Editing Frank Sinatra

{{Short description|American singer and actor (1915–1998)}}
{{Redirect|Sinatra}}
{{Good article}}
{{Use American English|date=January 2024}}
{{Use mdy dates|date=November 2023}}
{{Infobox person
| image              = Frank Sinatra (1957 studio portrait close-up).jpg
| caption            = Sinatra, {{circa|1957}}
| birth_name         = Francis Albert Sinatra
| birth_date         = {{birth date|1915|12|12}}
| birth_place        = [[Hoboken, New Jersey]], U.S.
| death_date         = {{death date and age|1998|5|14|1915|12|12}}
| death_place        = Los Angeles, California, U.S.
| burial_place       = [[Desert Memorial Park]]
| years_active       = 1935–1995
| works              = {{flatlist|
*[[Frank Sinatra discography|Albums and singles]]
*[[List of songs recorded by Frank Sinatra|songs]]
*[[Frank Sinatra filmography|filmography]]
}}
| signature          = Frank Sinatra signature.svg
| occupation         = {{flatlist|
*Singer
*actor
*producer
}}
| spouse             = {{plainlist|
* {{marriage|[[Nancy Barbato]] |February 4, 1939|October 29, 1951|end=divorced}}
* {{marriage|[[Ava Gardner]]|1951|1957|end=divorced}}
* {{marriage|[[Mia Farrow]]|July 19, 1966|1968|end=divorced}}
* {{marriage|[[Barbara Sinatra|Barbara Marx]]|July 11, 1976|<!--Year omitted per Template:Marriage instructions-->}}}}
| children           = {{flatlist|
* [[Nancy Sinatra|Nancy]]
* [[Frank Sinatra Jr.|Frank Jr.]]
* [[Tina Sinatra|Tina]]
}}
| parents            = {{plainlist|
* [[Anthony Martin Sinatra|Antonino Martino Sinatra]]
* [[Dolly Sinatra|Natalina Garaventa]]
}}
| module             = <!--Musical career embed infobox-->{{Infobox musical artist
 | embed  = yes
 | genre = {{flatlist|class=nowraplinks|
* [[Traditional pop]]
* [[easy listening]]
* [[jazz]]
* [[swing music|swing]]
* [[big band]]
}}
 | instrument = Vocals
 | label = {{flatlist|class=nowraplinks|
* [[RCA Victor]]
* [[Columbia Records|Columbia]]
* [[Capitol Records|Capitol]]
* [[Reprise Records|Reprise]]
* [[Warner Bros. Records|Warner Bros.]]
}}
| past_member_of = [[Rat Pack]]
}}
| website            = {{URL|sinatra.com}}
}}

'''Francis Albert Sinatra''' ({{IPAc-en|s|ᵻ|ˈ|n|ɑː|t|r|ə}}; December 12, 1915 – May 14, 1998) was an American singer and actor. Nicknamed the "[[Honorific nicknames in popular music|Chairman of the Board]]" and "Ol' Blue Eyes", he is regarded as one of the [[Time 100: The Most Important People of the Century|most popular entertainers of the 20th century]].<ref>{{Cite magazine |date=June 14, 1999 |title=TIME 100 Persons of The Century |url=https://content.time.com/time/subscriber/article/0,33009,991227-1,00.html |magazine=Time |via=content.time.com}}</ref> Sinatra is among the [[List of best-selling music artists|world's best-selling music artists]], with an estimated 150 million record sales globally.<ref>{{cite news|url=https://www.standard.co.uk/culture/theatre/ol-blue-eyes-frank-sinatra-is-coming-back-to-west-end-in-new-musical-a3262126.html|title=Blue Eyes Frank Sinatra ia coming back to west end in new musical|work=Evening Standard|access-date=June 21, 2021|archive-date=June 24, 2021|archive-url=https://web.archive.org/web/20210624205315/https://www.standard.co.uk/culture/theatre/ol-blue-eyes-frank-sinatra-is-coming-back-to-west-end-in-new-musical-a3262126.html|url-status=live}}</ref><ref>{{Cite web|last=Pisani|first=Bob|date=December 11, 2015|title=The business of Frank Sinatra|url=https://www.cnbc.com/2015/12/11/the-business-of-frank-sinatra.html|access-date=June 26, 2021|website=CNBC|language=en|archive-date=April 10, 2019|archive-url=https://web.archive.org/web/20190410082612/https://www.cnbc.com/2015/12/11/the-business-of-frank-sinatra.html|url-status=live}}</ref>

Born to [[Italian Americans|Italian immigrants]] in [[Hoboken, New Jersey]], Sinatra began his musical career in the [[swing era]] and was influenced by the easy-listening vocal style of [[Bing Crosby]].<ref>Giddens, Garry ''Bing Crosby: The Unsung King of Song'', published 2001</ref> He joined the [[Harry James]] band as the vocalist in 1939 before finding success as a solo artist after signing with [[Columbia Records]] in 1943, becoming the idol of the "[[Bobby-soxer|bobby soxers]]". In 1946, Sinatra released his debut album, ''[[The Voice of Frank Sinatra]]''. He then signed with [[Capitol Records]] and released several albums with arrangements by [[Nelson Riddle]], notably ''[[In the Wee Small Hours]]'' (1955) and ''[[Songs for Swingin' Lovers!]]'' (1956). In 1960, Sinatra left Capitol Records to start his own record label, [[Reprise Records]], releasing a string of successful albums. He collaborated with [[Count Basie]] on ''[[Sinatra-Basie: An Historic Musical First]]'' (1962) and ''[[It Might as Well Be Swing]]'' (1964). In 1965, he recorded ''[[September of My Years]]'' and starred in the [[Emmy]]-winning television special ''[[Frank Sinatra: A Man and His Music]]''. After releasing ''[[Sinatra at the Sands]]'' in 1966, Sinatra recorded one of his most famous collaborations with [[Tom Jobim]], ''[[Francis Albert Sinatra & Antonio Carlos Jobim]]''. It was followed by 1968's ''[[Francis A. & Edward K.]]'' with [[Duke Ellington]]. Sinatra retired in 1971 following the release of "[[My Way]]" but came out of retirement two years later. He recorded several albums and released "[[Theme from New York, New York|New York, New York]]" in 1980.

Sinatra also forged a highly successful acting career. After winning the [[Academy Award for Best Supporting Actor]] for ''[[From Here to Eternity]]'' (1953), he starred in ''[[The Man with the Golden Arm]]'' (1955) and ''[[The Manchurian Candidate (1962 film)|The Manchurian Candidate]]'' (1962). Sinatra also appeared in musicals such as ''[[On the Town (film)|On the Town]]'' (1949), ''[[Guys and Dolls (film)|Guys and Dolls]]'' (1955), ''[[High Society (1956 film)|High Society]]'' (1956), and ''[[Pal Joey (film)|Pal Joey]]'' (1957), which won him a [[Golden Globe Award for Best Actor – Motion Picture Musical or Comedy|Golden Globe Award]]. Toward the end of his career, he frequently played detectives, including the title character in ''[[Tony Rome]]'' (1967). Sinatra received the [[Golden Globe Cecil B. DeMille Award]] in 1971. On television, ''[[The Frank Sinatra Show (1950 TV series)|The Frank Sinatra Show]]'' began on [[CBS]] in 1950, and he continued to make appearances on television throughout the 1950s and 1960s.

In 1983, Sinatra was honored at the [[Kennedy Center Honors]]. He was awarded the [[Presidential Medal of Freedom]] in 1985 and the [[Congressional Gold Medal]] in 1997. Sinatra received eleven [[Grammy Awards]], including the [[Grammy Trustees Award]], [[Grammy Legend Award]], and the [[Grammy Lifetime Achievement Award]]. American music critic [[Robert Christgau]] called him "the greatest singer of the 20th century"<ref name="Christgau" /> and he continues to be regarded as an iconic figure.{{sfn|Rojek|2004|p=1}}

== Early life ==
{{Main|Early life of Frank Sinatra}}

{{quote box|width=320px|bgcolor=#c6dbf7|align=right|quote="They'd fought through his childhood and continued to do so until her dying day. But I believe that to counter her steel will he'd developed his own. To prove her wrong when she belittled his choice of career{{nbsp}}... Their friction first had shaped him; that, I think, had remained to the end and a litmus test of the grit in his bones. It helped keep him at the top of his game."|source=—Sinatra's daughter Nancy on the importance of his mother Dolly in his life and character.{{sfn|Santopietro|2008|p=427}}}}
Francis Albert Sinatra{{efn|On his original birth certificate, Sinatra's name was recorded incorrectly as "Frank Sinestro", a clerical error. In May 1945, he officially corrected the name on his birth certificate to "Francis A. Sinatra".{{sfnm|1a1=Sinatra|1y=1995|1p=17|2a1=Summers|2a2=Swan|2y=2010|2p=15}}}} was born on December 12, 1915, in a tenement at 415 Monroe Street in [[Hoboken, New Jersey]],<ref>{{cite news|url=http://news.bbc.co.uk/2/hi/special_report/1998/05/98/sinatra/67911.stm|title=Frank Sinatra obituary|date=May 16, 1998|access-date=May 15, 2008|work=BBC News|archive-date=April 11, 2019|archive-url=https://web.archive.org/web/20190411080810/http://news.bbc.co.uk/2/hi/special_report/1998/05/98/sinatra/67911.stm|url-status=live}}</ref>{{sfn|Sinatra|1995|p=15}}{{efn|The house at 415 Monroe Street burned down and no longer exists.<ref name="NJ">{{cite web|url=http://www.nj.com/hobokennow/index.ssf/2010/03/frank_sinatra_for_hoboken_tour.html|title=Frank Sinatra's dwindling tourist turf in Hoboken|work=The Jersey Journal|date=March 31, 2010|access-date=October 6, 2015|archive-date=November 10, 2016|archive-url=https://web.archive.org/web/20161110071744/http://www.nj.com/hobokennow/index.ssf/2010/03/frank_sinatra_for_hoboken_tour.html|url-status=live}}</ref> The site is marked by a brick archway with a bronze plaque on the sidewalk that reads, "Francis Albert Sinatra: The Voice".<ref name="NJ" /> The building at 417 Monroe Street has a "From Here to Eternity", sign with images of an Oscar statue.<ref>{{cite web|url=https://www.google.com/maps/place/417+Monroe+St,+Hoboken,+NJ+07030,+USA/@40.7434928,-74.0407959,17z/data=!3m1!4b1!4m5!3m4!1s0x89c257677ec83b73:0xbff3dba59c2c59bf!8m2!3d40.7434928!4d-74.0386072|title=415 Monroe Street|publisher=Google Maps|access-date=October 6, 2015|archive-date=March 8, 2021|archive-url=https://web.archive.org/web/20210308155540/https://www.google.com/maps/place/417+Monroe+St,+Hoboken,+NJ+07030,+USA/@40.7434928,-74.0407959,17z/data=!3m1!4b1!4m5!3m4!1s0x89c257677ec83b73:0xbff3dba59c2c59bf!8m2!3d40.7434928!4d-74.0386072|url-status=live}}</ref> It was opened as a museum by Ed Shirak in 2001, but closed after five years due to maintenance issues.<ref name="NJ" />}} the only child of [[Italian People|Italian]] immigrants [[Dolly Sinatra|Natalina "Dolly" Garaventa]] and [[Anthony Martin Sinatra|Antonino Martino "Marty" Sinatra]].{{Sfn|Sinatra|1986|p=3}}{{sfn|Petkov|Mustazza|1995|p=113}}{{efn|Other sources incorrectly say Catania.{{sfnm|1a1=Howlett|1y=1980|1p=5|2a1=Summers|2a2=Swan|2y=2010|2pp=22–25|3a1=Kaplan|3y=2011|3p=8: 415 Monroe Street}}}} Sinatra weighed {{convert|13.5|lbs}} at birth and had to be [[Childbirth#Second stage: fetal expulsion|delivered]] with the aid of [[Forceps in childbirth|forceps]], which caused severe scarring to his left cheek, neck, and ear, and perforated his eardrum—which remained damaged for the rest of his life. His grandmother resuscitated him by running him under cold water until he gasped.{{sfnm|1a1=Kelley|1y=1986|1p=13|2a1=Travis|2y=2001|2p=1|3a1=Turner|3y=2004|3p=4}} Due to his injuries, his baptism at St. Francis Church in Hoboken was delayed until April 2, 1916.{{sfn|Sinatra|1995|p=16}} A childhood operation on his [[Mastoid part of the temporal bone|mastoid]] bone left major scarring on his neck, and during adolescence he was further scarred by [[Acne vulgaris|cystic acne]].{{sfn|Kaplan|2011|pp=4–5}} Sinatra was raised in the [[Catholic Church]].<ref>{{cite web|url=http://www.esquire.com/news-politics/a638/esq1003-oct-sinatra-rev/?click=main_sr|first=Gay|last=Talese|title=Frank Sinatra Has a Cold|work=Esquire|date=October 8, 2007|access-date=October 12, 2010|archive-date=February 28, 2015|archive-url=https://web.archive.org/web/20150228125520/http://www.esquire.com/news-politics/a638/esq1003-oct-sinatra-rev/?click=main_sr|url-status=live}}</ref>

Sinatra's mother was energetic and driven;{{sfn|Kaplan|2011|p=6}} biographers believe that she was the dominant factor in the development of her son's personality and self-confidence.{{Sfnm|1a1=Rojek|1y=2004|1p=25|2a1=Santopietro|2y=2008|2p=15}} Sinatra's fourth wife [[Barbara Sinatra|Barbara]] would later claim that Dolly "knocked him around a lot" when he was a child.{{sfn|Sinatra|2011|p=86}} Dolly became influential in Hoboken and in local [[Democratic Party (United States)|Democratic Party]] circles.{{sfn|Sann|1967|p=351}} She worked as a [[midwife]],{{sfn|Kaplan|2011|pp=8–9}} and according to Sinatra biographer [[Kitty Kelley]], ran an illegal abortion service that catered to Italian Catholic girls, for which she was nicknamed "Hatpin Dolly".{{sfn|Kelley|1986|p=28}}{{efn|Dolly was reportedly arrested six or seven times and convicted twice for providing illegal abortions,{{sfnm|1a1=Kuntz|1a2=Kuntz|1y=2000|1p=36|2a1=Summers|2a2=Swan|2y=2010|2p=16}} the first of which was in 1937.{{sfn|Kelley|1986|p=29}}}} She had a gift for languages and served as a local interpreter.{{sfn|Kaplan|2011|pp=6, 8–9}}

Sinatra's illiterate father was a [[bantamweight]] boxer{{sfnm|1a1=Howlett|1y=1980|1p=5|2a1=Kaplan|2y=2011|2p=7}} who later worked at the Hoboken Fire Department, working his way up to captain.{{sfn|Goldstein|1982|p=2}} Due to his illiteracy, he stressed the importance of a "complete and full" education and had instilled in his son the desire to become a civil engineer and enroll at [[Stevens Institute of Technology]] in Hoboken.<ref>{{cite web|url=https://www.youtube.com/watch?v=xHUEvKyq7Zo|title=Frank Sinatra- Interview (snippet) 1975|date=September 18, 2019 |publisher=YouTube|accessdate=18 May 2024}}</ref> Sinatra spent much time at his parents' tavern in Hoboken,{{efn|In 1920, [[Prohibition in the United States|Prohibition]] of alcohol became law in the US. Dolly and Marty ran a tavern during those years, allowed to operate openly by local officials who refused to enforce the law.{{sfn|Kaplan|2011|pp=9–11}}}} working on his homework and occasionally singing for spare change.{{sfn|Kaplan|2011|p=11}} During the [[Great Depression]], Dolly provided money to her son for outings with friends and to buy expensive clothes, resulting in neighbors describing him as the "best-dressed kid in the neighborhood".{{sfn|Kelley|1986|pp=20–23}} Excessively thin and small as a child and young man, Sinatra's skinny frame later became a staple of jokes during stage shows.<ref name="SS">''Sinatra at the Sands'' (1966), [[Reprise Records]]</ref>{{sfn|Sinatra|2011|p=193}}

At a young age, Sinatra developed an interest in music, particularly [[big band]] jazz{{sfn|Rojek|2004|p=135}} and listened to [[Gene Austin]], [[Rudy Vallée]], [[Russ Colombo]], and [[Bob Eberly]] while idolizing [[Bing Crosby]].{{sfn|Lahr|2000|p=56}} For his 15th birthday, his uncle Domenico gave him a [[ukulele]], with which he performed at family gatherings.{{sfn|Donnelley|2003|p=642}} Sinatra attended David E. Rue Jr. High School from 1928,{{Sfn|Sinatra|1986|p=8}} and A. J. Demarest High School (since renamed as [[Hoboken High School]]) in 1931, where he arranged bands for school dances,{{sfn|Donnelley|2003|p=642}} but left without graduating after having attended only 47 days before being expelled for "general rowdiness".{{sfnm|1a1=Hodge|1y=1992|1p=8|2a1=Rojek|2y=2004|2p=135}} 

To please his mother, he enrolled at Drake Business School, but departed after 11 months.{{sfn|Donnelley|2003|p=642}} Dolly found her son work as a delivery boy at the ''Jersey Observer'' newspaper (since merged into ''[[The Jersey Journal]]''), where his godfather Frank Garrick worked;{{efn|Sinatra's loss of employment at the newspaper led to a life-long rift with Garrick. Dolly said of it, "My son is like me. You cross him, he never forgets."{{sfn|Lahr|2000|p=54}}}} he later worked as a riveter at the [[Tietjen & Lang Dry Dock Company|Tietjen and Lang]] shipyard.{{sfn|Summers|Swan|2010|pp=44, 47}}<ref>{{cite web|url=https://www.loc.gov/item/sn84026051/|title=Jersey Observer (Hoboken, N.J.) 1924–1951|publisher=Library of Congress|access-date=March 19, 2024}}</ref> He began performing in local Hoboken social clubs and sang for free on radio stations such as [[WNYM|WAAT]] in Jersey City.{{sfn|Kelley|1986|pp=44–45}} In New York, Sinatra found jobs singing for his supper or for cigarettes.{{sfn|Donnelley|2003|p=642}} To improve his speech, he began taking [[elocution]] lessons for a dollar each from vocal coach John Quinlan, one of the first people to notice his impressive vocal range.{{sfn|Kelley|1986|p=45}}

== Music career ==
{{See also|Frank Sinatra discography}}

=== 1935–1942: Hoboken Four, Harry James, and Tommy Dorsey ===
[[File:The Hoboken Four on the Major Bowes Amateur Hour.jpg|thumb|Sinatra (''far right'') with the [[Hoboken Four]] on ''[[Major Bowes' Amateur Hour]]'' in 1935]]
Sinatra began singing professionally as a teenager. He never learned to read music but [[Learning music by ear|learned by ear]].<ref>{{cite web | url=http://www.phoenixnewtimes.com/music/top-ten-things-that-make-frank-sinatra-cool-6614026 | title=Top Ten Things That Make Frank Sinatra Cool | work=Phoenix New Times | date=July 7, 2011 | access-date=September 28, 2015 | author=D'Andrea, Niki | archive-date=September 29, 2015 | archive-url=https://web.archive.org/web/20150929090722/http://www.phoenixnewtimes.com/music/top-ten-things-that-make-frank-sinatra-cool-6614026 | url-status=live }}</ref>{{sfn|Young|Young|2007|p=474}} He got his first break in 1935 when his mother persuaded a local singing group called the [[Hoboken Four|3 Flashes]] to let him join. [[Baritone]] Fred Tamburro stated that "Frank hung around us like we were gods or something", admitting that they only took him on board because he owned a car{{efn|Nancy Sinatra notes that he owned a Chrysler and people would show amazement that such a young kid could afford it.{{sfn|Sinatra|1986|p=18}}}} and could chauffeur the group. Sinatra soon learned they were auditioning for the ''[[Major Bowes Amateur Hour]]'' show and "begged" the group to let him join.{{sfn|Kelley|1986|p=39}} 

With Sinatra, the group became known as the "Hoboken Four" and passed an audition from [[Edward Bowes]] to appear on the show. They each earned $12.50,{{sfn|Santopietro|2008|p=25}} and attracted 40,000 votes to win first prize—a six-month contract to perform on stage and radio across the U.S.{{sfn|Rojek|2004|p=40}} Sinatra quickly became the group's lead singer, and, much to the jealousy of his fellow group members, garnered most of the attention from the girls.{{sfn|Kelley|1986|p=42}}{{efn|The jealousy exhibited by the group members often led to brawls in which they would beat up the small, skinny young Sinatra.{{sfn|Quirk|Schoell|1999|pp=19–20}}}} Due to the success of the group, Bowes kept asking for them to return, disguised under different names, varying from "The Secaucus Cockamamies" to "The Bayonne Bacalas".<ref name="SS" />

[[File:Frank Sinatra and Harry James at the Hollywood Canteen, 1943.jpg|thumb|left|Sinatra performing with [[Harry James]] at the [[Hollywood Canteen]] in 1943]]
In 1938, Sinatra found employment as a singing waiter at a [[Roadhouse (facility)#United States|roadhouse]] called "The Rustic Cabin" in [[Englewood Cliffs, New Jersey]], for which he was paid $15 a week.{{sfnm|1a1=Hodge|1y=1992|1p=11|2a1=Rojek|2y=2004|2p=41}} The roadhouse was connected to the [[WBBR|WNEW]] radio station in New York City, and he began performing with a group live during the ''Dance Parade'' show.{{sfn|Santopietro|2008|p=27}} Despite the low salary, Sinatra felt that this was the break he was looking for, and boasted to friends that he was going to "become so big that no one could ever touch him".{{sfn|Kelley|1986|p=46}} In March 1939, saxophone player Frank Mane, who knew Sinatra from Jersey City radio station WAAT, arranged for him to audition and record "[[Our Love (1939 song)|Our Love]]", his first solo studio recording.<ref name=CoyneK />{{efn| Only one copy of this recording was made, a 78{{nbsp}}rpm disc. Mane wrote "Frank Sinatra" on the record label and kept the recording in a drawer through the years, giving Sinatra a copy on a cassette tape as a gift in 1979. Mane died in 1998, only months after Sinatra's death; in 2006, Mane's widow offered the recording for sale through Gurnsey's auction house in New York.<ref name=CoyneK>{{cite news|url=https://query.nytimes.com/gst/fullpage.html?res=9F05E4D71F30F931A15753C1A9609C8B63|author=Coyne, Kevin|date=October 22, 2006|title=Sinatra's First, Freed at Last|work=The New York Times|access-date=September 1, 2015|archive-date=September 29, 2015|archive-url=https://web.archive.org/web/20150929202454/http://query.nytimes.com/gst/fullpage.html?res=9F05E4D71F30F931A15753C1A9609C8B63|url-status=live}}</ref>}} In June, bandleader [[Harry James]], who had heard Sinatra sing on "Dance Parade", signed him to a two-year contract of $75 a week after a show at the [[Paramount Theatre (New York City)|Paramount Theatre]] in New York.{{sfnm|1a1=Kelley|1y=1986|1p=53|2a1=Ingham|2y=2005|2p=9}}{{efn|The only sticking point was that James wanted Sinatra to change his name to Frankie Satin, as he thought that Sinatra sounded too Italian.{{sfn|Rotella|2010|p=8}} Neither Sinatra nor his mother would agree to this; he told James that his cousin, [[Ray Sinatra]], was a bandleader in Boston, kept his own name and was doing well with it. James actually knew Ray Sinatra, so he did not press the issue.<ref>{{cite web|url=http://www.discogs.com/artist/463189-Ray-Sinatra|title=Ray Sinatra|publisher=[[discogs]]|access-date=September 1, 2015|archive-date=May 24, 2015|archive-url=https://web.archive.org/web/20150524084341/http://www.discogs.com/artist/463189-Ray-Sinatra|url-status=live}}</ref><ref>{{cite magazine|url=https://books.google.com/books?id=MykEAAAAMBAJ&q=frank+sinatra&pg=PT66|title=The Sinatra Report|date=November 20, 1965|author=Simon, George T.|magazine=Billboard|access-date=September 1, 2015|archive-date=August 18, 2021|archive-url=https://web.archive.org/web/20210818191444/https://books.google.com/books?id=MykEAAAAMBAJ&q=frank+sinatra&pg=PT66|url-status=live}}</ref>}} It was with the James band that Sinatra released his first commercial record "From the Bottom of My Heart" in July. No more than 8,000 copies were sold,{{sfn|Petkov|Mustazza|1995|p=85}} and further records released with James through 1939, such as "[[All or Nothing at All]]", also had weak sales on their initial release.<ref name=rollingstone>{{cite news|title=Frank Sinatra|url=https://www.rollingstone.com/music/artists/frank-sinatra/biography|magazine=Rolling Stone|access-date=September 19, 2011|archive-date=September 20, 2011|archive-url=https://web.archive.org/web/20110920061203/http://www.rollingstone.com/music/artists/frank-sinatra/biography|url-status=live}}</ref> Thanks to his vocal training, Sinatra could now sing two tones higher, and developed a repertoire which included songs such as "[[My Buddy (song)|My Buddy]]", "[[Willow Weep for Me]]", "[[It's Funny to Everyone but Me]]", "Here Comes the Night", "[[On a Little Street in Singapore]]", "[[Ciribiribin]]", and "Every Day of My Life".{{sfn|Kelley|1986|p=55}}

[[File:Frank Sinatra and Tommy Dorsey, 1942 (close-up).jpg|thumb|Sinatra and [[Tommy Dorsey]] in ''[[Ship Ahoy (film)|Ship Ahoy]]'' (1942)]]
Sinatra became increasingly frustrated with the Harry James band, feeling that he was not achieving the major success and acclaim he was looking for. His pianist and close friend [[Hank Sanicola]] persuaded him to stay with the group,{{sfn|Kelley|1986|p=54}} but in November 1939 he left James to replace Jack Leonard{{efn|the vocalist, not to be confused with the comedian [[Jack E. Leonard]].}} as the lead singer of the [[Tommy Dorsey]] band. Sinatra earned $125 a week, appearing at the Palmer House in [[Chicago]],{{sfn|Wood|1996|p=135}} and James released Sinatra from his contract.<ref name=pc1a>{{Pop Chronicles 40s|1|A |url=https://digital.library.unt.edu/ark:/67531/metadc1633217/m1/#track/3}}</ref>{{efn|Sinatra acknowledged his debt to James throughout his life, and upon hearing of James' death in 1983, stated: "he is the one that made it all possible."{{sfn|Sinatra|1986|p=24}}}} 

On January 26, 1940, he made his first public appearance with the band at the [[Coronado Theatre]] in [[Rockford, Illinois]],{{sfn|Silva|2000|p=12}} opening the show with "[[Stardust (1927 song)|Stardust]]".{{sfn|Lees|1998|p=94}} Dorsey recalled: "You could almost feel the excitement coming up out of the crowds when the kid stood up to sing. Remember, he was no [[matinée idol]]. He was just a skinny kid with big ears. I used to stand there so amazed I'd almost forget to take my own solos".{{sfn|Lahr|2000|pp=59–60}} 

Dorsey was a major influence on Sinatra and became a [[father figure]]. Sinatra copied Dorsey's mannerisms and traits, becoming a demanding perfectionist like him, even adopting his hobby of toy trains. He asked Dorsey to be godfather to his daughter [[Nancy Sinatra|Nancy]] in June 1940.{{sfnm|1a1=Kelley|1y=1986|1pp=59–60|2a1=Lahr|2y=2000|2p=59}} Sinatra later said that "The only two people I've ever been afraid of are my mother and Tommy Dorsey."{{sfn|Kaplan|2011|p=1}} Though Kelley says that Sinatra and drummer [[Buddy Rich]] were bitter rivals,{{efn|Kelley says that arguments and fights regularly broke out between Sinatra and Rich, who were both arrogant with volatile tempers. In one incident witnessed by Stafford backstage at the [[Astor Hotel]] in New York, Rich called Sinatra a name, and Sinatra threw a heavy glass pitcher filled with water and ice at Rich's head. In another incident at the [[Golden Gate Theater]] in San Francisco, Rich reportedly attempted to ram Sinatra against the wall with his high F cymbal.{{sfn|Kelley|1986|pp=58–59}}}} other authors state that they were friends and even roommates when the band was on the road, but professional jealousy surfaced as both men wanted to be considered the star of Dorsey's band. Later, Sinatra helped Rich form his own band with a $25,000 loan and provided financial help to Rich during times of the drummer's serious illness.{{sfnm|1a1=Shaw|1y=1968|1p=34|2a1=Consiglio|2a2=Douskey|2y=2011|2p=135}}

In his first year with Dorsey, Sinatra recorded more than forty songs. Sinatra's first vocal hit was the song "[[Polka Dots and Moonbeams]]" in late April 1940.{{sfn|Whitburn|1986|p=136}} Two more chart appearances followed with "[[Say It (Frank Sinatra song)|Say It]]" and "[[Imagination (1940 song)|Imagination]]", which was Sinatra's first top-10 hit.{{sfn|Whitburn|1986|p=136}} His fourth chart appearance (and his first on the first officially published [[Billboard chart|''Billboard'' chart]])<ref name="bronson">{{cite book |url=https://books.google.com/books?id=RVFLAAAAYAAJ&pg=PA202 |title=The Billboard Book of Number One Hits |first= Fred |last=Bronson |date= 1997|isbn=9780823076413 |publisher=Billboard Books|page=202}}</ref> was "[[I'll Never Smile Again]]", topping the charts for twelve weeks beginning in mid-July.{{sfnm|1a1=Whitburn|1y=1986|1p=136|2a1=Summers|2a2=Swan|2y=2010|2p=91}} Other records with Tommy Dorsey issued by [[RCA Victor]] include "[[Our Love Affair]]" and "Stardust" in 1940; "[[Oh! Look at Me Now]]", "[[Dolores (song)|Dolores]]", "[[Everything Happens to Me (song)|Everything Happens to Me]]", and "[[This Love of Mine]]" in 1941; "[[Just as Though You Were There]]", "[[Take Me (Frank Sinatra song)|Take Me]]", and "[[There Are Such Things]]" in 1942; and "[[It Started All Over Again]]", "[[In the Blue of Evening]]", and "[[It's Always You]]" in 1943.{{sfn|Kelley|1986|pp=567–568}} 

As his success and popularity grew, Sinatra pushed Dorsey to allow him to record some solo songs. Dorsey eventually relented, and on January 19, 1942, Sinatra recorded "[[Night and Day (song)|Night and Day]]", "[[The Night We Called It a Day (song)|The Night We Called It a Day]]", "[[The Song is You]]", and "[[Lamplighter's Serenade]]" at a Bluebird recording session, with [[Axel Stordahl]] as arranger and conductor.{{sfnm|1a1=Kelley|1y=1986|1p=67|2a1=Lees|2y=1998|2p=97}} Sinatra first heard the recordings at the [[Hollywood Palladium]] and [[Hollywood Plaza Hotel|Hollywood Plaza]] and was astounded at how good he sounded. Stordahl recalled: "He just couldn't believe his ears. He was so excited you almost believed he had never recorded before. I think this was a turning point in his career. I think he began to see what he might do on his own".{{sfn|Kelley|1986|p=67}}

After the 1942 recordings, Sinatra believed he needed to go solo,{{sfn|Kelley|1986|pp=67–68}} with an insatiable desire to compete with [[Bing Crosby]],{{efn|Sinatra said: "The reason I wanted to leave Tommy's band was that Crosby was Number One, way up on top of the pile. In the open field, you might say, were some awfully good singers with the orchestras. [[Bob Eberly]] (with [[Jimmy Dorsey]]) was a fabulous vocalist. [[Perry Como|Mr. Como]] (with [[Ted Weems]]) is such a wonderful singer. I thought if I don't make a move out of this and try to do it on my own soon, one of those guys will do it, and I'll have to fight all three of them to get a position".{{sfn|Lahr|2000|p=60}}}} but he was hampered by his contract which gave Dorsey 43% of Sinatra's lifetime earnings.{{sfn|Lahr|2000|p=60}} A legal battle ensued, eventually settled in August 1942.{{sfn|Kelley|1986|p=70}}{{efn|Sinatra's lawyer, Henry Jaffe, met with Dorsey's lawyer N. Joseph Ross in Los Angeles in August 1943. In the words of Kelley: "In the end, MCA, an agency representing Dorsey and courting Sinatra, made Dorsey a $60,000 offer, which he accepted. To obtain Frank as a client, the agency paid Dorsey $35,000 while Sinatra paid $25,000, which he borrowed from Manie Sacks as an advance against his royalties from Columbia Records. MCA agreed that until 1948, it would split its commissions on Sinatra with GAC, the agency Frank had signed with when he left the Dorsey band."{{sfn|Kelley|1986|p=70}} However, during a 1979 concert at the [[Universal Amphitheatre]] in Los Angeles, Sinatra said that it took him years to escape the contract and that Dorsey had cost him 7{{nbsp}}million dollars.{{sfn|Kelley|1986|p=72}}}} On September 3, 1942, Dorsey bade farewell to Sinatra, reportedly saying "I hope you fall on your ass",{{sfn|Lahr|2000|p=60}} but he was more gracious on the air when replacing Sinatra with singer [[Dick Haymes]].<ref name="pc1a" /> 

Rumors began spreading in newspapers that Sinatra's mobster godfather, [[Willie Moretti]], coerced Dorsey at gunpoint to let Sinatra out of his contract for a few thousand dollars.{{sfn|Anastasia|Macnow|Pistone|2011|p=301}}{{efn|The incident started rumors of Sinatra's involvement with the Mafia and was fictionalized in the book and film ''The Godfather''.{{sfn|Levinson|2009|p=161}}}} Sinatra persuaded Stordahl to come with him and become his personal arranger, offering him $650 a month, five times his salary from Dorsey.{{Sfn|Goldstein|1982|p=9}} Dorsey and Sinatra, who had been very close, never reconciled their differences.{{sfn|Kelley|1986|p=71}}

=== 1942–1945: Onset of Sinatramania and Role in World War II ===
[[File:Sinatra Radio.gif|left|thumb|Sinatra with [[Alida Valli]], {{circa|1940}}s]]
{{blockquote|Perfectly simple: It was the war years, and there was a great loneliness, and I was the boy in every corner drugstore, the boy who'd gone off drafted to the war. That's all.|Sinatra, on his popularity with young women<ref name="tcm">{{Cite web |url=https://www.tcm.com/this-month/article/194235 |title=Ship Ahoy |last=Arnold |first=Jeremy |website=Turner Classic Movies |access-date=2018-12-16 |archive-date=December 16, 2018 |archive-url=https://web.archive.org/web/20181216074217/http://www.tcm.com/this-month/article/194235%7C0/Ship-Ahoy.html |url-status=live }}</ref>}}

By May 1941, Sinatra topped the male singer polls in ''[[Billboard (magazine)|Billboard]]'' and ''[[DownBeat]]'' magazines.{{sfn|Summers|Swan|2010|p=94}} His appeal to [[Bobby-soxer|bobby soxers]], as teenage girls of that time were called, revealed a new audience for popular music, which had previously been recorded mainly for adults.<ref>{{cite news|url=https://www.theguardian.com/century/1940-1949/Story/0,,127764,00.html|title=Frank Sinatra and the 'bobby-soxers'|newspaper=The Guardian|location=London|date=January 10, 1945|access-date=June 2, 2012|archive-date=November 16, 2020|archive-url=https://web.archive.org/web/20201116080008/https://www.theguardian.com/century/1940-1949/Story/0,,127764,00.html|url-status=live}}</ref> The phenomenon became officially known as "Sinatramania" after his "legendary opening" at the Paramount Theatre in New York on December 30, 1942.{{sfn|Lahr|2000|p=60}} 

According to Nancy Sinatra, [[Jack Benny]] later said, "I thought the goddamned building was going to cave in. I never heard such a commotion{{nbsp}}... All this for a fellow I never heard of."{{sfn|Sinatra|1986|p=44}} Sinatra performed for four weeks at the theatre, his act following the [[Benny Goodman]] orchestra, after which his contract was renewed for another four weeks by Bob Weitman due to his popularity. He became known as "Swoonatra" or "The Voice", and his fans "Sinatratics". They organized meetings and sent masses of letters of adoration, and within a few weeks of the show, some 1,000 Sinatra fan clubs had been reported across the US.{{sfn|Sinatra|1986|p=76}} 

Sinatra's publicist, George Evans, encouraged interviews and photographs with fans and was the man responsible for depicting Sinatra as a vulnerable, shy, Italian–American with a rough childhood who made good.{{sfn|Kelley|1986|pp=78, 99}} When Sinatra returned to the Paramount in October 1944, only 250 persons left the first show, and 35,000 fans left outside caused a near riot, known as the Columbus Day Riot, outside the venue because they were not allowed in.{{sfn|Roby|2010|p=111}}<ref>{{cite news|url=https://www.theguardian.com/music/2011/jun/11/frank-sinatra-pop-star|title=The Columbus Day riot: Frank Sinatra is pop's first star|newspaper=The Guardian|first=Jon|last=Savage|author-link=Jon Savage|date=June 11, 2011|access-date=October 19, 2015|archive-date=September 8, 2015|archive-url=https://web.archive.org/web/20150908023401/http://www.theguardian.com/music/2011/jun/11/frank-sinatra-pop-star|url-status=live}}</ref>{{sfn|Booker|2004|p=79}} Such was the bobby-soxer devotion to Sinatra that they were known to write Sinatra's song titles on their clothing, bribe hotel maids for an opportunity to touch his bed, and steal clothing he was wearing, most commonly his [[bow-tie|bow tie]].{{sfn|Booker|2004|pp=79–80}}

[[File:Ivan Ives - Sinatra Club - Wynyard Park.jpg|thumb|Young Sinatra fans listening to his records on a portable gramophone in [[Sydney, Australia]], 1945.]]
Sinatra signed with [[Columbia Records]] as a solo artist on June 1, 1943, during the [[1942–44 musicians' strike]].{{sfnm|1a1=Sinatra|1y=1986|1p=60|2a1=Ackelson|2y=1992|2p=6}} Columbia Records re-released Harry James and Sinatra's August 1939 version of "All or Nothing at All",{{sfn|Sinatra|1986|p=24}} which reached number 2 on June 2 and was on the best-selling list for 18 weeks.{{sfn|Peters|O'Brien|Sayers|1982|pp=123, 157}} He initially had great success,{{sfn|Shaw|1968|p=67}} and performed on the radio on ''[[Your Hit Parade]]'' from February 1943 until December 1944,{{sfn|Tyler|2007|p=267}} and on stage. 

Columbia wanted new recordings of their growing star as quickly as possible, so [[Alec Wilder]] was hired as an arranger and [[Conducting|conductor]] for several sessions with a vocal group called the Bobby Tucker Singers.{{sfn|Friedwald|1995|p=133}} Of the nine songs recorded during these sessions, seven charted on the best-selling list.<ref>{{Cite AV media notes|type=CD booklet|title=Frank Sinatra: The Columbia Years: 1943–1952, The Complete Recordings|year=1993}}</ref> That year he made his first solo nightclub appearance at New York's [[Riobamba (nightclub)|Riobamba]],{{sfn|Kaplan|2010|pp=88–89}} and a successful concert in the Wedgewood Room of the prestigious [[Waldorf-Astoria New York]] that year secured his popularity in New York high society.{{sfn|Kelley|1986|pp=93–95}} Sinatra released "[[You'll Never Know]]", "[[Close to You (1943 song)|Close to You]]", "[[Sunday, Monday, or Always]]" and "[[People Will Say We're in Love]]" as singles. By the end of 1943, he was more popular in a ''DownBeat'' poll than Bing Crosby.{{sfn|Kelley|1986|pp=96, 568}}

Sinatra did not serve in the military during World War II. On December 11, 1943, he was officially classified [[Class 1-A|4-F]] ("Registrant not acceptable for military service") by his draft board because of his perforated eardrum. However, Army files reported that Sinatra had actually been rejected because he was "not acceptable material from a psychiatric viewpoint;" his emotional instability was hidden to avoid "undue unpleasantness for both the selectee and the induction service".{{sfn|Santopietro|2008|p=45}} Briefly, there were rumors reported by columnist [[Walter Winchell]] that Sinatra paid $40,000 to avoid military service, but the FBI found this to be without merit.<ref>{{cite magazine|magazine=Billboard|title=Sinatra FBI Files Opened|first=Bill|last=Holland|url=https://books.google.com/books?id=KQoEAAAAMBAJ&q=walter+winchell|date=December 19, 1998|page=10|issn=0006-2510|access-date=October 9, 2018|archive-date=August 1, 2020|archive-url=https://web.archive.org/web/20200801195218/https://books.google.com/books?id=KQoEAAAAMBAJ&q=walter+winchell|url-status=live}}</ref>{{sfn|Newton|2003|p=314}}<ref>{{cite web|url=http://vault.fbi.gov/Frank%20Sinatra|title=The Vault — Frank Sinatra|work=FBI |publisher=[[Federal Bureau of Investigation|FBI]]|access-date=October 20, 2015|archive-date=April 26, 2021|archive-url=https://web.archive.org/web/20210426204352/https://vault.fbi.gov/Frank%20Sinatra/|url-status=live}}</ref>

[[File:Sinatra Shore Crosby AFRS.jpg|thumb|Sinatra (left) on the Armed Forces Radio in 1944 with [[Dinah Shore]] and [[Bing Crosby]] (right)]]
Toward the end of the war, Sinatra entertained the troops during several successful overseas [[USO]] tours with comedian [[Phil Silvers]].{{sfn|Andrews|Gilbert|1993|p=293}} During one trip to Rome, he met [[Pope Pius XII|the Pope]], who asked him if he was an operatic tenor.{{sfn|Kelley|1986|pp=115–116}} Sinatra worked frequently with the popular [[The Andrews Sisters|Andrews Sisters]] in radio in the 1940s,{{sfn|Nimmo|2004|p=228}} and many USO shows were broadcast to troops via the [[Armed Forces Radio Service]] (AFRS).{{sfn|Sforza|2015|p=80}} In 1944, Sinatra released "[[I Couldn't Sleep a Wink Last Night]]" as a single and recorded his own version of Irving Berlin's "[[White Christmas (song)|White Christmas]]". The following year he released "[[I Dream of You (More Than You Dream I Do)]]", "[[Saturday Night (Is the Loneliest Night of the Week)]]", "[[Dream (1944 song)|Dream]]", and "[[Nancy (with the Laughing Face)]]" as singles.{{sfn|Kelley|1986|p=568}}

=== 1946–1952: Columbia years and career slump ===
Despite being heavily involved in political activity in 1945 and 1946, in those two years, Sinatra sang on 160 radio shows, recorded 36 times, and shot four films. By 1946, he was performing on stage up to 45 times a week, singing up to 100 songs daily, and earning up to $93,000 a week.{{Sfn|Summers|Swan|2010|p=150}}

In 1946, Sinatra released "[[Oh! What it Seemed to Be]]", "[[Day by Day (1945 song)|Day by Day]]", "[[They Say It's Wonderful]]", "[[Five Minutes More]]", and "[[The Coffee Song]]" as singles,{{sfn|Kelley|1986|p=569}} and launched his first album, ''[[The Voice of Frank Sinatra]]'',{{sfn|Rojek|2004|p=43}} which reached No. 1 on the ''Billboard'' chart. William Ruhlmann of AllMusic wrote that Sinatra "took the material very seriously, singing the love lyrics with utter seriousness" and that his "singing and the classically influenced settings gave the songs unusual depth of meaning."<ref>{{cite web|url=http://www.allmusic.com/album/the-voice-of-frank-sinatra-mw0000659223|title=The Voice of Frank Sinatra|website=AllMusic|access-date=October 28, 2015|archive-date=October 24, 2015|archive-url=https://web.archive.org/web/20151024012157/http://www.allmusic.com/album/the-voice-of-frank-sinatra-mw0000659223|url-status=live}}</ref> He was soon selling 10{{nbsp}}million records a year.{{sfn|Kelley|1986|p=129}} 

Such was Sinatra's command at Columbia that his love of conducting was indulged with the release of the set ''[[Frank Sinatra Conducts the Music of Alec Wilder]]'', an offering unlikely to appeal to Sinatra's core fanbase of teenage girls at the time.{{sfn|Gigliotti|2002|p=21}} The following year he released his second album, ''[[Songs by Sinatra]]'', featuring songs of a similar mood and tempo such as [[Irving Berlin]]'s "[[How Deep is the Ocean?]]" and [[Harold Arlen]]'s and [[Jerome Kern]]'s "[[All The Things You Are]]".{{sfn|Osborne|2014|p=98}} "[[Mam'selle]]", composed by [[Edmund Goulding]] with lyrics by [[Mack Gordon]] for the film ''[[The Razor's Edge (1946 film)|The Razor's Edge]]'' (1946),{{Sfn|Kennedy|2004|p=236}} was released as a single.{{Sfn|Kelley|1986|p=569}} 

Sinatra had competition; versions by [[Art Lund]], [[Dick Haymes]], [[Dennis Day]], and The Pied Pipers also reached the top ten of the ''Billboard'' charts.<ref>{{cite magazine|url=https://books.google.com/books?id=6h8EAAAAMBAJ&q=Mam%27selle+billboard&pg=PA23|magazine=Billboard|title=Most Played Juke Box Records|page=23|date=May 31, 1947|issn=0006-2510|access-date=October 17, 2020|archive-date=August 19, 2021|archive-url=https://web.archive.org/web/20210819013311/https://books.google.com/books?id=6h8EAAAAMBAJ&q=Mam%27selle+billboard&pg=PA23|url-status=live}}</ref> In December, he recorded "[[Sweet Lorraine]]" with the [[Metronome All-Stars]], featuring talented jazz musicians such as [[Coleman Hawkins]], [[Harry Carney]] and [[Charlie Shavers]], with [[Nat King Cole]] on piano, in what Charles L. Granata describes as "one of the highlights of Sinatra's Columbia epoch".{{Sfn|Granata|2003|p=50}}

Sinatra's third album, ''[[Christmas Songs by Sinatra]]'', was originally released in 1948 as a 78{{nbsp}}rpm album set,{{sfn|Granata|2003|pp=47–48}} and a 10" LP record was released two years later.{{sfn|Larkin|2002|p=397}} When Sinatra was featured as a priest in ''[[The Miracle of the Bells]]'', due to press negativity surrounding his alleged Mafia connections at the time,{{efn|Sinatra was spotted in Havana in 1946 with mobster [[Lucky Luciano]], which started a series of negative press articles, implicating Sinatra with the Mafia.{{sfn|Hanna|1998|p=21}} In 1947, he was involved in a violent incident with journalist [[Lee Mortimer]], who had written some of the most scathing articles on his alleged connections. Kelley says that his articles grew so offensive that Sinatra pounced on him outside Ciro's and punched him behind the left ear in response to an insult in which he was called a "dago". Sinatra was taken to court, and according to Kelley, Mortimer received Mafia threats to drop the case or lose his life.{{sfn|Kelley|1986|pp=139–141}}}} it was announced to the public that Sinatra would donate his $100,000 in wages from the film to the [[Catholic Church]].{{sfn|Hanna|1998|p=21}} 

By the end of 1948, Sinatra had slipped to fourth on ''DownBeat''{{'}}s annual poll of most popular singers,{{sfn|Summers|Swan|2010|p=149}} and in the following year he was pushed out of the top spots in polls for the first time since 1943.{{Sfn|Kelley|1986|p=158}} ''[[Frankly Sentimental]]'' (1949) was panned by ''DownBeat'', who commented that "for all his talent, it seldom comes to life."{{Sfn|Shaw|1968|p=131}}

[[File:Frank Sinatra Metronome magazine November 1950.JPG|thumb|left|upright|Sinatra in November 1950]]
Though "[[The Hucklebuck]]" reached the top ten,{{Sfn|Sinatra|1986|p=301}} it was his last single release under the Columbia label.{{Sfn|Kelley|1986|p=569}} Sinatra's last two albums with Columbia, ''[[Dedicated to You (Frank Sinatra album)|Dedicated to You]]'' and ''[[Sing and Dance with Frank Sinatra]]'', were released in 1950.{{sfn|Granata|2003|p=218}} Sinatra would later feature a number of the ''Sing and Dance with Frank Sinatra'' album's songs, including "[[Lover (Rodgers and Hart song)|Lover]]", "[[It's Only a Paper Moon (song)|It's Only a Paper Moon]]", and "[[It All Depends on You]]", on his 1961 Capitol release, ''[[Sinatra's Swingin' Session!!!]]''.{{sfn|Granata|2003|p=67}}

Culminating the low of his career was the death of publicist George Evans in January 1950. According to [[Jimmy Van Heusen]], Sinatra's close friend and songwriter, Evans's death to him was "an enormous shock which defies words", as he had been crucial to his career and popularity with the "[[Bobby soxer (subculture)|Bobby soxers]]".{{Sfn|Kelley|1986|p=161}} 

Sinatra's reputation continued to decline as reports broke in February of his affair with Ava Gardner and the destruction of his marriage to Nancy,{{sfn|Small|2009|p=59}} though he insisted that his marriage had long been over even before he met Gardner.{{Sfn|Kelley|1986|p=162}} In April, Sinatra was engaged to perform at the [[Copacabana (nightclub)|Copa]] club in New York, but had to cancel five days of the booking due to a submucosal hemorrhage of the throat.{{Sfn|Kelley|1986|pp=168–169}} Evans once said that whenever Sinatra suffered from a bad throat and loss of voice it was always due to emotional tension, which "absolutely destroyed him".{{Sfn|Summers|Swan|2010|p=151}}

[[File:The Desert Inn Vegas 1968.jpg|thumb|The [[Desert Inn]], Las Vegas, where Sinatra began performing in 1951]]
In financial difficulty following his divorce and career decline, Sinatra was forced to borrow $200,000 from Columbia to pay his back taxes after MCA refused to front the money.{{Sfn|Kelley|1986|p=172}} Rejected by Hollywood, he turned to [[Las Vegas]] and made his debut at the [[Desert Inn]] in September 1951,{{sfn|Shaw|1982|p=48}} and also began singing at the Riverside Hotel in [[Reno, Nevada]]. 

Sinatra's decline in popularity was evident in his concert appearances. At a brief run at the Paramount in New York, he drew small audiences.{{sfn|Summers|Swan|2010|p=164}} At the Desert Inn in Las Vegas, he performed to half-filled houses.{{sfn|Summers|Swan|2010|p=529}} At a concert at [[Chez Paree]] in Chicago, only 150 people turned up in a 1,200-seat venue.{{sfn|Kaplan|2011|p=529}} By April 1952, he was performing at the [[Kauai County Fair]] in Hawaii.{{sfn|Sinatra|1986|p=93}} Sinatra's relationship with Columbia Records was disintegrating, with [[Artists and repertoire|A&R]] executive [[Mitch Miller]] claiming he "couldn't give away" Sinatra records.{{sfn|Summers|Swan|2010|p=164}}{{efn|Miller tried to offset Sinatra's declining record sales by introducing "gimmicky novel tunes" in his repertoire, such as "Mama Will Bark" to appeal to younger audiences.<ref name="columbia-yrs-hemming-36">{{Cite AV media notes |title=The Best of the Columbia Years: 1943–1952 |title-link=The Best of the Columbia Years: 1943–1952 |year=1995 |chapter=Sinatra Standards |first=Hemming |last=Roy |page=36 |type=booklet |publisher=SONY Music Entertainment |id=C4K 64681 |location=New York }}</ref>{{sfn|Kaplan|2011|pp=476–477}} "Mama Will Bark" is often cited as the worst of Sinatra's career. Miller thought he would try this novelty approach for Sinatra because he felt his "great records" were not selling.{{sfn|Granata|2003|p=74}} Initially, Sinatra went along with this approach, but eventually, he came to resent Miller for the poor material he was being offered.{{sfn|Kaplan|2011|pp=476, 509}}}} Though several notable recordings were made during this time period, such as "[[I Could Write a Book|If I Could Write a Book]]" in January 1952, which Granata sees as a "turning point", forecasting his later work with its sensitivity,{{sfn|Granata|2003|p=74}} 

Columbia and MCA dropped him later that year.{{sfn|Granata|2003|p=76}} His last studio recording for Columbia, "Why Try To Change Me Now", was recorded in New York on September 17, 1952, with an orchestra arranged and conducted by [[Percy Faith]].{{sfn|Kaplan|2011|p=535}} Journalist [[Burt Boyar]] observed, "Sinatra had had it. It was sad. From the top to the bottom in one horrible lesson."{{sfn|Summers|Swan|2010|p=164}}

=== 1953–1960: Career revival and the Capitol years ===
[[File:Nelson Riddle 1958.JPG|thumb|[[Nelson Riddle]], Sinatra's album arranger for Capitol Records]]
The release of the film ''[[From Here to Eternity]]'' in August 1953 marked the beginning of a remarkable career revival.{{sfn|Kidder|Oppenheim|2008|p=157}} [[Tom Santopietro]] notes that Sinatra began to bury himself in his work, with an "unparalleled frenetic schedule of recordings, movies and concerts",{{Sfn|Santopietro|2008|p=187}} in what authors Anthony Summers and Robbyn Swan describe as "a new and brilliant phase".{{sfn|Summers|Swan|2010|p=188}} 

On March 13, 1953, Sinatra met with Capitol Records vice president [[Alan Livingston]] and signed a seven-year recording contract.{{sfn|Kaplan|2011|pp=601}} His first session for Capitol took place at KHJ studios at Studio C, 5515 Melrose Avenue in Los Angeles, with Axel Stordahl conducting.{{sfn|Kaplan|2011|pp=604, 615}} The session produced four recordings, including "[[I'm Walking Behind You]]",{{sfn|Kaplan|2011|p=604}} Sinatra's first Capitol single.{{sfn|Sinatra|1986|p=101}} 

After spending two weeks on location in Hawaii filming ''From Here to Eternity'', Sinatra returned to KHJ on April 30 for his first recording session with [[Nelson Riddle]], an established arranger and conductor at Capitol who was Nat King Cole's musical director.{{sfn|Kaplan|2011|pp=614–615, 618}} After recording the first song, "[[I've Got the World on a String]]", Sinatra offered Riddle a rare expression of praise, "Beautiful!",{{sfn|Kaplan|2011|p=616}} and after listening to the playbacks, he could not hide his enthusiasm, exclaiming, "I'm back, baby, I'm back!"{{sfn|Summers|Swan|2010|p=191}}

[[File:Frank Sinatra (1957 Pal Joey publicity photo).jpg|thumb|Sinatra in 1957 publicity shot]]
In subsequent sessions in May and November 1953,{{sfn|Kline|1990|p=33}} Sinatra and Riddle developed and refined their musical collaboration, with Sinatra providing specific guidance on the arrangements.{{sfn|Summers|Swan|2010|p=191}} Sinatra's first album for Capitol, ''[[Songs for Young Lovers]]'', was released on January 4, 1954, and included "[[A Foggy Day]]", "[[I Get a Kick Out of You]]", "[[My Funny Valentine]]", "[[Violets for Your Furs]]", and "[[They Can't Take That Away from Me]]",{{sfnm|1a1=Kline|1y=1990|1p=18|2a1=Granata|2y=2003|2p=91}} songs which became staples of his later concerts.<ref name="SS" /><ref name="SC57" /> 

That same month, Sinatra released the single "[[Young at Heart (Frank Sinatra song)|Young at Heart]]", which reached No. 2 and was awarded Song of the Year.{{sfnm|1a1=Sinatra|1y=1986|1p=103|2a1=O'Brien|2y=2014}}<ref>{{cite web|url=http://sinatrafamily.com/single/young-at-heart-125/|title=Young at Heart|publisher=Sinatra Discography|access-date=September 5, 2015|archive-date=September 25, 2015|archive-url=https://web.archive.org/web/20150925104833/http://sinatrafamily.com/single/young-at-heart-125/|url-status=live}}</ref><ref>{{cite web|url=http://www.allmusic.com/album/young-at-heart-mw0000867619/awards|title=Young at Heart album awards|website=AllMusic|access-date=September 5, 2015|archive-date=September 25, 2015|archive-url=https://web.archive.org/web/20150925232314/http://www.allmusic.com/album/young-at-heart-mw0000867619/awards|url-status=live}}</ref>{{efn|Sinatra was not very enthusiastic about the song initially. His friend, Jimmy Van Heusen, convinced him that the song would be a success.{{sfn|O'Brien|2014}} ''Young at Heart'' was produced by Day's husband at the time, [[Marty Melcher]], whom Sinatra detested. Their feud grew worse when Melcher suggested that Day sing "Young at Heart" as the film's title song when Sinatra's recording of the song was already a hit—Day conceded that she did not care whose voice was heard singing the film's title song. Because of the rift, the ''Young at Heart'' soundtrack album contains all the songs heard in the film but the title ''Young at Heart''. Sinatra's hit recording is heard at the beginning and end of the film.{{sfn|Bret|2014|p=63}}}} In March, he recorded and released the single "[[Three Coins in the Fountain (song)|Three Coins in the Fountain]]", a "powerful ballad"<ref name="Inc.1954">{{cite magazine|magazine=Billboard|title=The Billboard Music Popularity Charts|url=https://books.google.com/books?id=YB8EAAAAMBAJ&pg=PA22|date=May 8, 1954|page=22|issn=0006-2510|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429120208/https://books.google.com/books?id=YB8EAAAAMBAJ&pg=PA22|url-status=live}}</ref> that reached No. 4.{{sfn|Kline|1990|p=19}} Sinatra's second album with Riddle, ''[[Swing Easy!]]'', which reflected his "love for the jazz idiom" according to Granata,{{sfn|Granata|2003|p=91}} was released on August 2 of that year and included "[[Just One of Those Things (song)|Just One of Those Things]]", "[[Taking a Chance on Love]]", "[[Get Happy (song)|Get Happy]]", and "[[All of Me (Ruth Etting song)|All of Me]]".{{sfn|Kline|1990|p=19}}<ref name="Inc.1965">{{cite magazine|magazine=Billboard|title=The Sinatra Discography|url=https://books.google.com/books?id=MykEAAAAMBAJ&pg=PT117|date=November 20, 1965|page=117|issn=0006-2510|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429084115/https://books.google.com/books?id=MykEAAAAMBAJ&pg=PT117|url-status=live}}</ref> ''Swing Easy!'' was named Album of the Year by ''Billboard'', and he was named "Favorite Male Vocalist" by ''Billboard'', ''DownBeat'', and ''[[Metronome]]'' that year.{{sfnm|1a1=Sinatra|1y=1986|1p=103|2a1=Evanier|2y=2011|2p=99}}<ref>{{cite magazine|magazine=Billboard|title=Artists Favorites|url=https://books.google.com/books?id=LCEEAAAAMBAJ&pg=PA42|date=November 13, 1954|page=42|issn=0006-2510|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429112532/https://books.google.com/books?id=LCEEAAAAMBAJ&pg=PA42|url-status=live}}</ref> 

Sinatra came to consider Riddle "the greatest arranger in the world",{{sfn|Summers|Swan|2010|p=192}} and Riddle, who considered Sinatra, "a perfectionist",{{sfn|Summers|Swan|2010|p=191}} said: "It's not only that his intuitions as to tempo, phrasing, and even configuration are amazingly right, but his taste is so impeccable{{nbsp}}... There is still no one who can approach him."{{sfn|Summers|Swan|2010|p=192}}

Sinatra became one of Las Vegas's pioneer [[concert residency|residency]] entertainers,<ref>{{cite book|title=The New York Times Biographical Service, Volume 29 – Las Vegas Playground And Kennedy Campaign|url=https://books.google.com/books?id=eN8zAQAAIAAJ|date=May 1998|publisher=New York Times & Arno Press|page=745|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429140318/https://books.google.com/books?id=eN8zAQAAIAAJ|url-status=live}}</ref> and a prominent figure on the Vegas scene [[Las Vegas in the 1950s|throughout the 1950s]] and 1960s onwards, a period described by Rojek as the "high-water mark" of Sinatra's "hedonism and self-absorption". Rojek notes that the [[Rat Pack]] "provided an outlet for gregarious banter and wisecracks" but argues that it was Sinatra's vehicle, possessing an "unassailable command over the other performers".{{sfn|Rojek|2004|p=136}} Sinatra would fly to Las Vegas from Los Angeles in Van Heusen's plane.{{sfn|Sinatra|2011|p=97}} On October 4, 1953, Sinatra made his first performance at the [[Sands Hotel and Casino]], after an invitation by the manager [[Jack Entratter]].{{sfn|Clarke|2004|p=189}}{{sfn|Ainlay|Gabaldon|2003|p=108}} Sinatra typically performed there three times a year and later acquired a share in the hotel.{{sfnm|1a1=Kelley|1y=1986|1p=243|2a1=Kaplan|2y=2011|2p=656}}{{efn|Sinatra bought a two percent share in the hotel for $54,000.{{sfn|Kaplan|2011|p=656}} At one point the share reached nine percent.{{Sfn|Kelley|1986|p=245}} He was reportedly ordered to sell his interest in the Sands in 1963, due to his association with mobster [[Sam Giancana]].<ref>{{cite news|url=https://www.newspapers.com/clip/2881720/sinatra_drives_golf_cart_through_sands/|title=Sinatra Hit in Mouth in Vegas Melee|work=The Times ([[San Mateo, California]])|date=September 12, 1967|page=8|access-date=July 29, 2015|via=[[Newspapers.com]]|archive-date=October 30, 2021|archive-url=https://web.archive.org/web/20211030014852/https://www.newspapers.com/clip/2881720/sinatra-drives-golf-cart-through-sands/|url-status=live}} {{Open access}}</ref>}}

[[File:Frank Sinatra (circa 1955 in Capitol Studios).jpg|thumb|Sinatra recording at [[Capitol Studios]], {{circa|1955}}]]
In 1955, Sinatra released ''[[In the Wee Small Hours]]'', his first 12" LP,{{Sfn|Smith|2009|p=18}} featuring songs such as "[[In the Wee Small Hours of the Morning]]", "[[Mood Indigo]]", "[[Glad to Be Unhappy]]" and "[[When Your Lover Has Gone]]".<ref>{{cite web|url=http://www.allmusic.com/album/in-the-wee-small-hours-mw0000650776|title=In the Wee Small Hours|website=AllMusic|access-date=October 9, 2015|archive-url=https://web.archive.org/web/20140204131932/http://www.allmusic.com/album/in-the-wee-small-hours-mw0000650776|archive-date=February 4, 2014}}</ref> According to Granata it was the first [[concept album]] of his to make a "single persuasive statement", with an extended program and "melancholy mood".{{Sfn|Granata|2003|p=91}} Sinatra embarked on his first tour of Australia the same year.{{sfn|Sinatra|1986|p=302}} 

Another collaboration with Riddle resulted in ''[[Songs for Swingin' Lovers!]]'', sometimes seen as one of his best albums, which was released in March 1956.{{Sfn|Weatherford|2001|p=14}} It features a recording of "[[I've Got You Under My Skin]]" by [[Cole Porter]],<ref>{{cite book|url=https://books.google.com/books?id=1_i5f3jhD9UC|title=The New York Times Guide to the Arts of the 20th Century: 1900–1929 – A New Family and A New Fame|publisher=Taylor & Francis|year=2002|page=3072|isbn=978-1-57958-290-6|access-date=August 28, 2017|archive-date=August 1, 2020|archive-url=https://web.archive.org/web/20200801202454/https://books.google.com/books?id=1_i5f3jhD9UC|url-status=live}}</ref> which reportedly took 22 takes to perfect.{{Sfn|Granata|2003|p=102}}

His February 1956 recording sessions inaugurated the studios at the [[Capitol Records Building]],{{sfn|Gigliotti|2002|p=22}} complete with a 56-piece symphonic orchestra.{{sfn|Granata|2003|p=117}} According to Granata, his recordings of "Night and Day", "Oh! Look at Me Now", and "[[From This Moment On (Cole Porter song)|From This Moment On]]" revealed "powerful sexual overtones, stunningly achieved through the mounting tension and release of Sinatra's best-teasing vocal lines", while his recording of "River, Stay 'Way from My Door" in April demonstrated his "brilliance as a syncopational improviser".{{sfn|Granata|2003|p=98}} 

Riddle said that Sinatra took "particular delight" in singing "The Lady is a Tramp", commenting that he "always sang that song with a certain amount of salaciousness", making "cue tricks" with the lyrics.{{sfn|Friedwald|1995|p=236}} His penchant for conducting was displayed again in 1956's ''[[Frank Sinatra Conducts Tone Poems of Color]]'', an instrumental album that has been interpreted to be a catharsis to his failed relationship with Gardner.{{sfn|Gigliotti|2002|pp=21–22}} Sinatra also sang at [[1956 Democratic National Convention|that year's Democratic National Convention]] and performed with [[The Dorsey Brothers]] for a week soon afterward at the Paramount Theatre.{{sfn|Turner|2004|p=95}}

[[File:Pal Joey trailer1957.ogv|thumb|left|upright=0.9|thumbtime=120|Sinatra introducing his character to the audience in the 1957 trailer for the film ''[[Pal Joey (film)|Pal Joey]]'']]
In 1957, Sinatra released ''[[Close to You (Frank Sinatra album)|Close to You]]'', ''[[A Swingin' Affair!]]'', and ''[[Where Are You? (Frank Sinatra album)|Where Are You?]]''—his first album in stereo, with [[Gordon Jenkins]].{{sfn|Morrell|2013|p=40}} Granata considers "Close to You" to have been thematically his closest concept album to perfection during the "golden" era, and Nelson Riddle's finest work, which was "extremely progressive" by the standards of the day. It is structured like a three-act play, each commencing with the songs "[[With Every Breath I Take]]", "[[Blame It on My Youth]]" and "[[It Could Happen to You (song)|It Could Happen to You]]".{{Sfn|Granata|2003|p=121}} For Granata, Sinatra's ''A Swingin' Affair!'' and ''Songs for Swingin' Lovers!'' solidified "Sinatra's image as a 'swinger', from both a musical and visual standpoint." [[Buddy Collette]] considered the swing albums to have been heavily influenced by [[Sammy Davis Jr.]] and stated that when he worked with Sinatra in the mid-1960s, he approached a song much differently than he had done in the early 1950s.{{Sfn|Granata|2003|p=102}} 

On June 9, 1957, he performed in a 62-minute concert conducted by Riddle at the [[McCaw Hall|Seattle Civic Auditorium]],{{sfn|Levinson|2001|p=138}} his first appearance in [[Seattle]] since 1945.<ref name="SC57">''Sinatra '57 in Concert'' (1999), [[Artanis Entertainment Group]].</ref> The recording was first released as a bootleg, but [[Artanis Entertainment Group]] officially released it as ''[[Sinatra '57 in Concert]]'' in 1999, after Sinatra's death.<ref name="LAT99">{{cite web|author=Hilburn, Robert|url=https://www.latimes.com/archives/la-xpm-1999-jun-11-ca-45246-story.html|title=Getting a Kick Out of Sinatra, Live in Concert in 1957|work=Los Angeles Times|date=June 11, 1999|access-date=October 5, 2015|archive-date=December 10, 2015|archive-url=https://web.archive.org/web/20151210220825/http://articles.latimes.com/1999/jun/11/entertainment/ca-45246|url-status=live}}</ref> 

In 1958, Sinatra released the concept album ''[[Come Fly with Me (Frank Sinatra album)|Come Fly with Me]]'' with [[Billy May]], designed as a musical world tour.{{Sfnm|1a1=Mirtle|1y=1998|1pp=154–155|2a1=Turner|2y=2004|2p=107}} It reached the top spot on the ''Billboard'' album chart in its second week, remaining at the top for five weeks,{{sfn|Whitburn|2001|p=797}} and was nominated for the [[Grammy Award for Album of the Year]] at the [[1st Grammy Awards|inaugural Grammy Awards]].{{Sfn|Mirtle|1998|p=155}} The title song, "[[Come Fly with Me (1957 song)|Come Fly With Me]]", written especially for him, would become one of his best-known standards.<ref>{{cite book|title=London Theatre Record, Volume 7, Issues 14–26 – Sammy Cahn Words And Music|url=https://books.google.com/books?id=uClaAAAAMAAJ|year=1987|publisher=I. Herbert|page=888|access-date=October 20, 2015|archive-date=April 27, 2016|archive-url=https://web.archive.org/web/20160427042307/https://books.google.com/books?id=uClaAAAAMAAJ|url-status=live}}</ref> On May 29, he recorded seven songs in a single session, more than double the usual yield of a recording session, and an eighth, "[[Lush Life (jazz song)|Lush Life]]", was abandoned as Sinatra found it too technically demanding.{{sfn|Granata|2003|pp=141–142}} In September, Sinatra released ''[[Frank Sinatra Sings for Only the Lonely]]'', a stark collection of introspective{{efn|Granata noted that Riddle himself believed that the album came across as darker and more introspective than normal due to the death of his own mother who had recently died earlier in the month that it was recorded.{{sfn|Granata|2003|p=139}}}} saloon songs and blues-tinged ballads, which proved a huge commercial success, spending 120 weeks on ''Billboard''{{'}}s album chart and peaking at No. {{nbsp}}1.{{sfn|Ackelson|1992|p=11}} Cuts from this LP, such as "[[Angel Eyes (1946 song)|Angel Eyes]]" and "[[One for My Baby (and One More for the Road)]]", would remain staples of the "saloon song" segments of Sinatra's concerts.<ref>{{cite book|title=The Mojo Collection: 4th Edition{{nbsp}}– Frank Sinatra Sings For Only The Lonely|url=https://books.google.com/books?id=AVQbF9lTBwgC&pg=PA22|date=November 1, 2007|publisher=Canongate Books|isbn=978-1-84767-643-6|page=22|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429125201/https://books.google.com/books?id=AVQbF9lTBwgC&pg=PA22|url-status=live}}</ref>

[[File:Frank Sinatra2, Pal Joey.jpg|thumb|Sinatra in ''Pal Joey'' (1957)]]
In 1959, Sinatra released ''[[Come Dance with Me! (album)|Come Dance with Me!]]'', a highly successful, critically acclaimed album that stayed on ''Billboard''{{'}}s Pop album chart for 140 weeks, peaking at No. 2. It won the Grammy Award for Album of the Year, as well as [[Grammy Award for Best Vocal Performance, Male|Best Vocal Performance, Male]] and [[Grammy Award for Best Arrangement|Best Arrangement]] for Billy May.{{sfn|Granata|2003|p=143}} 

He released ''[[No One Cares]]'' in the same year, a collection of "brooding, lonely" torch songs, which critic [[Stephen Thomas Erlewine]] thought was "nearly as good as its predecessor ''Where Are You?'', but lacked the "lush" arrangements of it and the "grandiose melancholy" of ''Only the Lonely''.<ref>{{cite web|url=http://www.allmusic.com/album/no-one-cares-mw0000312462|title=No One Cares|website=AllMusic|access-date=October 12, 2015|archive-date=October 12, 2015|archive-url=https://web.archive.org/web/20151012093455/http://www.allmusic.com/album/no-one-cares-mw0000312462|url-status=live}}</ref>

In the words of Kelley, by 1959, Sinatra was "not simply the leader of the Rat Pack" but had "assumed the position of ''il padrone'' in Hollywood." He was asked by 20th Century Fox to be the master of ceremonies at a luncheon attended by Soviet Premier [[Nikita Khrushchev]] on September 19, 1959.{{sfn|Kelley|1986|pp=287–288}} ''[[Nice 'n' Easy]]'', a collection of ballads, topped the ''Billboard'' chart in October 1960 and remained in the charts for 86 weeks,{{Sfn|Fuchs|Prigozy|2007|p=101}} winning critical plaudits.{{Sfn|Campbell|2008|p=220}}<ref>{{cite magazine|magazine=Billboard|title=Cap Captures Honors at Disc Jockey Poll|url=https://books.google.com/books?id=lx0EAAAAMBAJ&pg=PA2|date=December 19, 1960|page=2|issn=0006-2510|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429111245/https://books.google.com/books?id=lx0EAAAAMBAJ&pg=PA2|url-status=live}}</ref>

=== 1960–1969: Reprise years ===
Sinatra grew discontented at Capitol and feuded with [[Alan Livingston]], which lasted over six months.{{Sfn|Granata|2003|p=146}} His first attempt at owning his own label was with his pursuit of buying declining jazz label [[Verve Records]], which ended once an initial agreement with Verve founder [[Norman Granz]] "failed to materialize".<ref>{{Cite web|url=http://ultimateclassicrock.com/reprise-records-history/|title=To Play and Play Again: How Frank Sinatra's Thirst for Creative Freedom Led to Some of Classic Rock's Greatest Records|website=Ultimate Classic Rock|date=February 13, 2016 |access-date=October 28, 2017|archive-date=August 19, 2017|archive-url=https://web.archive.org/web/20170819193252/http://ultimateclassicrock.com/reprise-records-history/|url-status=live}}</ref> 

He decided to form his own label, [[Reprise Records]],{{Sfnm|1a1=Friedwald|1y=1995|1p=367|2a1=Rojek|2y=2004|2p=142}} and, in an effort to assert his new direction, temporarily parted with Riddle, May and Jenkins, working with other arrangers such as [[Neil Hefti]], [[Don Costa]], and [[Quincy Jones]].{{Sfn|Granata|2003|p=153}} Sinatra built the appeal of Reprise Records as one in which artists were promised creative control, as well as a guarantee that they would eventually gain "complete ownership of their work, including publishing rights."<ref>{{Cite web|url=http://www.rhino.com/article/label-retrospective-sinatra-forms-reprise-records-on-this-day-in-1960|title=Label Retrospective: Sinatra forms Reprise Records on this day in 1960 {{!}} Rhino|website=www.rhino.com|language=en|access-date=October 28, 2017|archive-date=October 29, 2017|archive-url=https://web.archive.org/web/20171029065325/http://www.rhino.com/article/label-retrospective-sinatra-forms-reprise-records-on-this-day-in-1960|url-status=live}}</ref> 

Under Sinatra the company developed into a music industry "powerhouse", and he later sold it for an estimated $80{{nbsp}}million.{{sfn|Santopietro|2008|p=340}} His first album on the label, ''[[Ring-a-Ding-Ding!]]'' (1961), was a major success, peaking at No.4 on ''Billboard''.<ref>{{cite magazine|magazine=Billboard|title=Cliff Richard a Four-Time Winner|url=https://books.google.com/books?id=jiAEAAAAMBAJ&pg=PA26|date=December 11, 1961|first=Espen|last=Eriksen|page=26|issn=0006-2510|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429140520/https://books.google.com/books?id=jiAEAAAAMBAJ&pg=PA26|url-status=live}}</ref> The album was released in February 1961, the same month that Reprise Records released [[Ben Webster]]'s ''[[The Warm Moods]]'', [[Sammy Davis Jr.]]'s ''The Wham of Sam'', [[Mavis Chloe Rivers|Mavis River]]'s ''Mavis'' and [[Joe E. Lewis]]'s ''It is Now Post Time''.{{sfn|Friedwald|1995|p=377}} During the initial years of Reprise, Sinatra was still under contract to record for Capitol, completing his contractual commitment with the release of ''[[Point of No Return (Frank Sinatra album)|Point of No Return]]'', recorded on September 11 and 12, 1961.{{sfn|Granata|2003|p=149}}

[[File:Dean Martin, Judy Garland and Frank Sinatra in 1962.jpg|thumb|left|Sinatra with [[Dean Martin]] and [[Judy Garland]] in 1962]]
In 1962, Sinatra released ''[[Sinatra and Strings]]'', a set of standard ballads arranged by Don Costa, which became one of the most critically acclaimed works of Sinatra's Reprise period. Frank Jr., who was present during the recording, noted the "huge orchestra", which Nancy Sinatra stated "opened a whole new era" in pop music, with orchestras getting bigger, embracing a "lush string sound".{{Sfn|Granata|2003|p=162}} 

Sinatra and [[Count Basie]] collaborated for the album ''[[Sinatra–Basie: An Historic Musical First|Sinatra-Basie]]'' the same year,{{sfn|Shaw|1982|p=25}} a popular and successful release which prompted them to rejoin two years later for the follow-up ''[[It Might as Well Be Swing]]'', arranged by Quincy Jones.{{sfnm|1a1=Sinatra|1y=1986|1p=372|2a1=Granata|2y=2003|2p=169}} The two became frequent performers together,<ref>{{cite magazine|magazine=Billboard|title=The Sinatra Report|url=https://books.google.com/books?id=MykEAAAAMBAJ&pg=PT36|date=November 20, 1965|page=36|issn=0006-2510|access-date=October 20, 2015|archive-date=April 25, 2016|archive-url=https://web.archive.org/web/20160425135258/https://books.google.com/books?id=MykEAAAAMBAJ&pg=PT36|url-status=live}}</ref> and appeared at the [[Newport Jazz Festival]] in 1965.{{sfn|Sinatra|1986|p=302}} Also in 1962, as the owner of his own record label, Sinatra was able to step on the podium as conductor again, releasing his third instrumental album ''[[Frank Sinatra Conducts Music from Pictures and Plays]]''.{{sfn|Gigliotti|2002|p=22}}

In 1963, Sinatra reunited with Nelson Riddle for ''[[The Concert Sinatra]]'', an ambitious album featuring a 73-piece symphony orchestra arranged and conducted by Riddle. The concert was recorded on a motion picture scoring soundstage with the use of multiple synchronized recording machines that employed an optical signal onto 35{{nbsp}}mm film designed for movie soundtracks. Granata considers the album to have been "impeachable" [sic], "one of the very best of the Sinatra-Riddle ballad albums", in which Sinatra displayed his vocal range, particularly in "[[Ol' Man River]]", in which he darkened the hue.{{sfn|Granata|2003|pp=171–173}}

In 1964, the song "[[My Kind of Town]]" was nominated for the [[Academy Award for Best Original Song]].<ref>{{cite web | url=https://www.oscars.org/oscars/ceremonies/1965 | title=The 37th Academy Awards | date=October 5, 2014 | publisher=Academy of Motion Picture Arts and Sciences | access-date=October 4, 2015 | archive-date=October 31, 2014 | archive-url=https://web.archive.org/web/20141031093059/https://www.oscars.org/oscars/ceremonies/1965 | url-status=live }}</ref> Sinatra released ''[[Softly, as I Leave You (album)|Softly, as I Leave You]]'',<ref>{{cite web|url=http://www.allmusic.com/album/softly-as-i-leave-you-mw0000653242|title=Softly, as I Leave You|website=AllMusic|access-date=October 8, 2015|archive-date=October 12, 2015|archive-url=https://web.archive.org/web/20151012080304/http://www.allmusic.com/album/softly-as-i-leave-you-mw0000653242|url-status=live}}</ref> and collaborated with Bing Crosby and [[Fred Waring]] on ''[[America, I Hear You Singing]]'', a collection of patriotic songs recorded as a tribute to the assassinated President John F. Kennedy.{{Sfn|Avant-Mier|2010|p=15}}<ref>{{cite magazine|magazine=Billboard|title=Album Reviews|url=https://books.google.com/books?id=iEUEAAAAMBAJ&pg=PT1|date=May 9, 1964|page=1|issn=0006-2510|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429125407/https://books.google.com/books?id=iEUEAAAAMBAJ&pg=PT1|url-status=live}}</ref> Sinatra increasingly became involved in charitable pursuits in this period. In 1961 and 1962, he went to Mexico to put on performances for Mexican charities. {{efn|Nancy Sinatra notes that her father had a falling out with a bureaucrat in the country, who refused to admit Sinatra into his house. She says that though he was not formally banned from the country, the bureaucrat "made it seem so" and stated that the situation caused much humiliation to the family.{{Sfn|Sinatra|1986|p=212}}}} and in July 1964, he was present at the dedication of the Frank Sinatra International Youth Center for Arab and Jewish children in [[Nazareth]].{{sfn|Turner|2004|p=144}}

Sinatra's phenomenal success in 1965, coinciding with his 50th birthday, prompted ''Billboard'' to proclaim that he may have reached the "peak of his eminence".<ref name="Billboard 0598" /> In June 1965, Sinatra, Sammy Davis Jr., and [[Dean Martin]] played live in [[St. Louis]] to benefit Dismas House, a prisoner rehabilitation and training center with nationwide programs that, in particular, helped serve black Americans. 

The Rat Pack concert, called The Frank Sinatra Spectacular, was broadcast live via satellite to numerous movie theaters across America.<ref>{{cite web | url=https://variety.com/1997/film/news/rat-pack-perf-found-1117433048/ | title=Rat pack perf found | work=Variety | date=January 26, 1997 | access-date=October 4, 2015 | author=Richmond, Ray | archive-date=October 5, 2015 | archive-url=https://web.archive.org/web/20151005124153/http://variety.com/1997/film/news/rat-pack-perf-found-1117433048/ | url-status=live }}</ref><ref>{{Cite journal|url=https://muse.jhu.edu/article/649439|title=Frank Sinatra and the Hoodlum Priest|first=Stephen|last=Werner|date=April 5, 2016|journal=American Catholic Studies|volume=127|issue=4|pages=101–108|via=Project MUSE|doi=10.1353/acs.2016.0074|s2cid=185983040|access-date=August 9, 2018|archive-date=August 9, 2018|archive-url=https://web.archive.org/web/20180809215503/https://muse.jhu.edu/article/649439|url-status=live|issn=2161-8534}}</ref> The album ''[[September of My Years]]'' was released September 1965, and went on to win the Grammy Award for best album of the year.{{sfnm|1a1=Sinatra|1y=1986|1p=306|2a1=Jackson|2y=2015|2p=178}} Granata considers the album to have been one of the finest of his Reprise years, "a reflective throwback to the concept records of the 1950s, and more than any of those collections, distills everything that Frank Sinatra had ever learned or experienced as a vocalist".{{Sfn|Granata|2003|p=175}} One of the album's singles, "[[It Was a Very Good Year]]", won the Grammy Award for Best Vocal Performance, Male.<ref>{{cite web|url=http://www.grammy.com/awards/8th-annual-grammy-awards|title=8th Annual Grammy Awards|publisher=National Academy of Recording Arts and Sciences|access-date=October 6, 2015|archive-date=October 7, 2015|archive-url=https://web.archive.org/web/20151007154853/http://www.grammy.com/awards/8th-annual-grammy-awards|url-status=live}}</ref> A career anthology, ''[[A Man and His Music]]'', followed in November, winning Album of the Year at the Grammys the following year.<ref>{{cite web|url=http://www.grammy.com/awards/9th-annual-grammy-awards|title=9th Annual Grammy Awards|publisher=National Academy of Recording Arts and Sciences|access-date=October 9, 2015|archive-date=September 24, 2015|archive-url=https://web.archive.org/web/20150924044822/http://www.grammy.com/awards/9th-annual-grammy-awards|url-status=live}}</ref>

In 1966, Sinatra released ''[[That's Life (Frank Sinatra album)|That's Life]]'', with both the single of "[[That's Life (song)|That's Life]]" and album becoming Top Ten hits on ''Billboard''{{'}}s pop charts.<ref>{{cite magazine | url=http://www.billboard.com/charts/hot-100/1966-12-31 | title=The Hot 100 – December 31, 1966 | magazine=Billboard | date=December 31, 1966 | access-date=October 4, 2015 | archive-date=September 9, 2015 | archive-url=https://web.archive.org/web/20150909051550/http://www.billboard.com/charts/hot-100/1966-12-31 | url-status=live }}</ref> ''[[Strangers in the Night]]'' went on to top the ''Billboard'' and UK pop singles charts,<ref name="UKCharts">{{cite web | url=http://www.officialcharts.com/chart-news/all-the-number-1-singles__7931/ | title=All The Number 1 Singles | publisher=Official Charts Company | date=January 30, 2015 | access-date=October 4, 2015 | archive-date=October 4, 2015 | archive-url=https://web.archive.org/web/20151004120737/http://www.officialcharts.com/chart-news/all-the-number-1-singles__7931/ | url-status=live }}</ref><ref>{{cite magazine | url=http://www.billboard.com/charts/hot-100/1966-07-02 | title=The Hot 100 – July 2, 1966 | magazine=Billboard | date=July 2, 1966 | access-date=October 4, 2015 | archive-date=February 11, 2016 | archive-url=https://web.archive.org/web/20160211191248/http://www.billboard.com/charts/hot-100/1966-07-02 | url-status=live }}</ref> winning the award for Record of the Year at the Grammys.<ref>{{cite web | url=http://www.grammy.com/nominees/search?artist=&title=&year=1966&genre=All | title=1966 Winners | publisher=National Academy of Recording Arts and Sciences | access-date=October 4, 2015 | archive-date=May 11, 2011 | archive-url=https://web.archive.org/web/20110511195922/http://www.grammy.com/nominees/search?artist=&title=&year=1966&genre=All | url-status=live }}</ref> Sinatra's first live album, ''[[Sinatra at the Sands]]'', was recorded during January and February 1966 at the Sands Hotel and Casino in Las Vegas. Sinatra was backed by the Count Basie Orchestra, with Quincy Jones conducting.{{sfn|Lonstein|Marino|1970|p=324}} Sinatra pulled out from the Sands the following year when he was driven out by its new owner [[Howard Hughes]] after a fight.{{sfn|Jones|1995|p=25}}{{efn|Hughes still resented Sinatra for marrying Ava Gardner, the subject of his own affections.{{sfn|Jones|1995|p=25}} After Hughes saw to it that the hotel imposed restrictions on what he could gamble in the casino,<ref>{{cite news|url=https://www.newspapers.com/clip/2881690/san_antonio_express/|title=Jimmy Despises Casino Gambling|author=Snyder, Jimmy "the Greek"|date=July 3, 1975|work=San Antonio Express|page=8|access-date=July 29, 2015|via=[[Newspapers.com]]|archive-date=October 1, 2015|archive-url=https://web.archive.org/web/20151001194934/http://www.newspapers.com/clip/2881690/san_antonio_express/|url-status=live}} {{Open access}}</ref> Sinatra began what ''[[The Los Angeles Times]]'' describes as a "weekend-long tirade" against the "hotel's management, employees and security forces",<ref>{{cite web|url=https://www.latimes.com/archives/la-xpm-1986-12-30-me-1117-story.html|title=Ex-Casino Executive Carl Cohen; Noted for Punching Frank Sinatra|work=Los Angeles Times|date=December 30, 1986|access-date=July 25, 2015|archive-date=October 2, 2015|archive-url=https://web.archive.org/web/20151002055655/http://articles.latimes.com/1986-12-30/local/me-1117_1_carl-cohen|url-status=live}}</ref> culminating in a punch from executive [[Carl Cohen (businessman)|Carl Cohen]] that knocked the caps off Sinatra's front teeth.{{sfn|Anka|Dalton|2013|pp=168–171}} He began performing at [[Caesars Palace]].{{sfn|Sheridan|2011|p=54}}}}

[[File:Frank Sinatra Jill St. John Tony Rome.jpg|thumb|upright|Sinatra with [[Jill St. John]] in ''[[Tony Rome]]'' (1967)]]
Sinatra started 1967 with a series of recording sessions with [[Antônio Carlos Jobim]]. He recorded one of his collaborations with Jobim, the Grammy-nominated album ''[[Francis Albert Sinatra & Antônio Carlos Jobim]]'', which was one of the best-selling albums of the year, behind the Beatles's ''[[Sgt. Pepper's Lonely Hearts Club Band]]''.<ref>{{cite book|title=Jazz Education Journal, Volume 37, Issues 4–6 – Talking with Paolo Jobim about Antônio Carlos Jobim and the continuation of his legacy|url=https://books.google.com/books?id=snIJAQAAMAAJ|year=2005|publisher=International Association for Jazz Education|pages=7–8|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429091631/https://books.google.com/books?id=snIJAQAAMAAJ|url-status=live}}</ref> 

According to Santopietro the album "consists of an extraordinarily effective blend of bossa nova and slightly swinging jazz vocals, and succeeds in creating an unbroken mood of romance and regret."{{Sfn|Santopietro|2008|p=387}} Writer [[Stan Cornyn]] wrote that Sinatra sang so softly on the album that it was comparable to the time that he suffered from a vocal hemorrhage in 1950.{{sfn|Granata|2003|p=183}}

Sinatra released the album ''[[The World We Knew]]'', which features a chart-topping duet of "[[Somethin' Stupid]]" with daughter Nancy.<ref name="UKCharts" /><ref>{{cite magazine | url=http://www.billboard.com/articles/columns/chart-beat/6531810/rewinding-the-charts-in-1967-frank-nancy-sinatra-shared-a-no-1 | title=Rewinding the Charts: In 1967, Frank & Nancy Sinatra Shared a No. 1 | magazine=Billboard | date=April 15, 2015 | access-date=October 4, 2015 | author=Caulfield, Keith | archive-date=September 29, 2015 | archive-url=https://web.archive.org/web/20150929064656/http://www.billboard.com/articles/columns/chart-beat/6531810/rewinding-the-charts-in-1967-frank-nancy-sinatra-shared-a-no-1 | url-status=live }}</ref> In December, Sinatra collaborated with [[Duke Ellington]] on the album ''[[Francis A. & Edward K.]]''.<ref>{{cite magazine|magazine=Billboard|title=Album Reviews|url=https://books.google.com/books?id=rAcEAAAAMBAJ&pg=RA1-PA78|date=February 3, 1968|page=78|issn=0006-2510|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429084201/https://books.google.com/books?id=rAcEAAAAMBAJ&pg=RA1-PA78|url-status=live}}</ref> According to Granata, the recording of "[[Indian Summer (Victor Herbert song)|Indian Summer]]" on the album was a favorite of Riddle's, noting the "contemplative mood [which] is heightened by a [[Johnny Hodges]] alto sax solo that will bring a tear to your eye".{{sfn|Granata|2003|p=189}} 

With Sinatra in mind, singer-songwriter [[Paul Anka]] wrote the song "[[My Way]]", using the melody of the French "Comme d'habitude" ("As Usual"), composed by [[Claude François]] and [[Jacques Revaux]].{{sfn|Ingham|2005|p=270}} Sinatra recorded it in one take, just after Christmas 1968.{{Sfn|Friedwald|1995|p=446}} "My Way", Sinatra's best-known song on the Reprise label, was not an instant success, charting at No. 27 in the US and No. 5 in the UK.{{sfn|Kutner|2010|p=296}} However, it remained in the UK charts for 122 weeks, including 75 non-consecutive weeks in the [[American Top 40|Top 40]], between April 1969 and September 1971, which was still a record in 2015.<ref>{{cite web|title=Frank Sinatra |url=http://www.officialcharts.com/artist/15791/frank-sinatra/|publisher=[[Official Charts Company]]|access-date=October 8, 2015|archive-date=October 1, 2015|archive-url=https://web.archive.org/web/20151001051256/http://www.officialcharts.com/artist/15791/frank-sinatra/|url-status=live}}</ref><ref>{{cite news|title=Sheeran hit first to remain a year in UK chart|url=http://www.rte.ie/ten/news/2015/0624/710330-sheeran-hit-first-to-remain-a-year-in-uk-chart/|access-date=October 8, 2015|publisher=[[Raidió Teilifís Éireann]] Ten |date=June 24, 2015|archive-date=August 2, 2015|archive-url=https://web.archive.org/web/20150802123126/http://www.rte.ie/ten/news/2015/0624/710330-sheeran-hit-first-to-remain-a-year-in-uk-chart/|url-status=dead }}</ref> Sinatra told songwriter [[Ervin Drake]] in the 1970s that he "detested" singing the song because he believed audiences would think it was a "self-aggrandizing tribute".{{sfn|Granata|2003|p=xvii}} According to [[NPR]], "My Way" has become one of the most requested songs at funerals.<ref>{{Cite news |title=A Toast To 'My Way', America's Anthem Of Self-Determination |language=en |publisher=NPR |work=All Things Considered |first=Sonari |last=Glinton |date=November 19, 2019 |series=American Anthem |url=https://www.npr.org/2019/11/19/774805536/frank-sinatra-my-way-self-determination-american-anthem |access-date=June 6, 2022}}</ref>

In an effort to maintain his commercial viability in the late 1960s, Sinatra would record works by [[Paul Simon]] ("[[Mrs. Robinson]]"), [[the Beatles]] ("[[Yesterday (Beatles song)|Yesterday]]"), and [[Joni Mitchell]] ("[[Both Sides, Now]]") in 1969.<ref>{{cite magazine | url=http://www.time.com/time/time100/artists/profile/sinatra2.html|archive-url=https://web.archive.org/web/20071005141811/http://www.time.com/time/time100/artists/profile/sinatra2.html|archive-date=October 5, 2007|title=Frank Sinatra&nbsp;– The Time 100 Profile|magazine=Time| url-status=dead|access-date=October 24, 2015}}</ref>

=== 1970–1981: "Retirement" and return ===
[[File:Caesars Palace in 1970.jpg|thumb|left|[[Caesars Palace]] in 1970, where Sinatra performed from 1967 to 1970 and 1973 onwards]]
In 1970, Sinatra released ''[[Watertown (album)|Watertown]]'', a critically acclaimed concept album, with music by [[Bob Gaudio]] (of the Four Seasons) and lyrics by [[Jake Holmes]].{{sfn|Ingham|2005|p=216}} However, it sold a mere 30,000 copies that year and reached a peak chart position of 101.{{sfn|Knight|2010|p=260}} 

He left Caesars Palace in September of that year after an incident in which executive Sanford Waterman pulled a gun on him.{{efn|Sinatra was playing a high stakes [[Baccarat (card game)|baccarat]] at Caesars Palace in the early morning of September 6, 1970. Normal limits for the game are US$2,000 per hand; Sinatra had been playing for US$8,000 and wanted the stakes to be raised to US$16,000.<ref>{{cite news|url=https://www.newspapers.com/clip/3360435/sinatra_confrontation_at_caesars/|title=At Gunpoint Sinatra Ousted|work=The Odessa American ([[Odessa, Texas]])|date=September 7, 1970|page=11|access-date=October 6, 2015|via=[[Newspapers.com]]|archive-date=October 6, 2015|archive-url=https://web.archive.org/web/20151006191252/http://www.newspapers.com/clip/3360435/sinatra_confrontation_at_caesars/|url-status=live}} {{Open access}}</ref> When Sinatra began shouting, hotel executive Sanford Waterman came to talk with him. Witnesses said Waterman and Sinatra both made threats, and Waterman pointed a gun at Sinatra. Sinatra returned to Palm Springs without completing his three-week engagement. Waterman was arrested<ref>{{cite news|url=https://www.newspapers.com/clip/3360441/sinatra_confrontation_at_caesars_2/|title=Caesars Palace Boss Arrested for Pulling Gun on Sinatra|work=The Evening Times ([[Sayre, Pennsylvania]])|date=September 8, 1970|page=5|access-date=October 6, 2015|via=[[Newspapers.com]]|archive-date=October 6, 2015|archive-url=https://web.archive.org/web/20151006185830/http://www.newspapers.com/clip/3360441/sinatra_confrontation_at_caesars_2/|url-status=live}} {{Open access}}</ref> but not prosecuted.<ref>{{cite news|url=https://www.newspapers.com/clip/3360451/sinatra_confrontation_at_caesars/|title=No Charges Will be Filed in Sinatra Gun Incident|work=The Bridgeport Telegram ([[Bridgeport, Connecticut]])|date=September 17, 1970|page=45|access-date=October 6, 2015|via=[[Newspapers.com]]|archive-date=October 6, 2015|archive-url=https://web.archive.org/web/20151006181635/http://www.newspapers.com/clip/3360451/sinatra_confrontation_at_caesars/|url-status=live}} {{Open access}}</ref>}} He performed several charity concerts with Count Basie at the [[Royal Festival Hall]] in London.{{sfn|Sinatra|1986|p=307}} On November 2, 1970, Sinatra recorded the last songs for Reprise Records before his self-imposed retirement,{{sfn|Ackelson|1992|p=415}} announced the following June at a concert in Hollywood to raise money for the Motion Picture and TV Relief Fund.<ref>{{cite magazine|magazine=Billboard|title=Retirement Isn't The Life For Francis Albert|first=Laura|last=Deni|url=https://books.google.com/books?id=EwkEAAAAMBAJ&pg=PA35|date=November 24, 1973|page=35|issn=0006-2510|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429140515/https://books.google.com/books?id=EwkEAAAAMBAJ&pg=PA35|url-status=live}}</ref> He gave a "rousing" performance of "That's Life", and finished the concert with a [[Matt Dennis]] and Earl Brent song, "Angel Eyes" which he had recorded on the ''Only the Lonely'' album in 1958.<ref>Sinatra The Chairman James Kaplan pages 845–46</ref> He sang the last line. "'Scuse me while I disappear." The spotlight went dark, and he left the stage.{{Sfn|Sinatra|1986|p=223}} 

He told ''LIFE'' journalist [[Thomas Thompson (American author)|Thomas Thompson]] that "I've got things to do, like the first thing is not to do {{em|anything}} at all for eight months{{nbsp}}... maybe a year",{{sfn|Granata|2003|p=191}} while Barbara Sinatra later said that Sinatra had grown "tired of entertaining people, especially when all they really wanted were the same old tunes he had long ago become bored by".{{sfn|Sinatra|2011|p=102}} Around this time, Sinatra designed ''Villa Maggio'', a holiday home and retreat near [[Palm Desert]].<ref>{{cite web |last1=Pitcher |first1=Greg |title=Frank Sinatra's Californian desert hideaway, with three houses, helipad and parking for 24 cars on sale for £3.4m |url=https://www.standard.co.uk/homesandproperty/celebrity-homes/frank-sinatra-villa-maggio-california-desert-house-for-sale-b1125551.html |website=Evening Standard |date=December 12, 2023 |access-date=27 December 2023}}</ref> While he was in retirement, President [[Richard Nixon]] asked him to perform at a Young Voters Rally in anticipation of the upcoming campaign. Sinatra obliged and chose to sing "My Kind of Town" for the rally held in Chicago on October 20, 1972.{{sfn|Sinatra|1986|p=231}}

[[File:Frank Sinatra Standing with President Richard Nixon, Pat Nixon, and President of the Council of Ministers of the Italian Republic Giulio Andreotti.jpg|thumb|Sinatra with President [[Richard Nixon]] and Italian Prime Minister [[Giulio Andreotti]] in 1973]]
In 1973, Sinatra came out of his short-lived retirement with a television special and album. The album, entitled ''[[Ol' Blue Eyes Is Back]]'',{{Sfn|Knight|2010|p=260}} arranged by Gordon Jenkins and [[Don Costa]],{{sfn|Granata|2003|p=224}} was a success, reaching number 13 on ''Billboard'' and number 12 in the UK.<ref>{{cite magazine|magazine=Billboard|title=Jazzmen Favor|url=https://books.google.com/books?id=EwkEAAAAMBAJ&pg=RA1-PA26|date=November 24, 1973|page=26|issn=0006-2510|access-date=October 20, 2015|archive-date=April 26, 2016|archive-url=https://web.archive.org/web/20160426205643/https://books.google.com/books?id=EwkEAAAAMBAJ&pg=RA1-PA26|url-status=live}}</ref>{{Sfn|Gillett|1978|p=438}} The television special, ''[[Magnavox Presents Frank Sinatra]]'', reunited Sinatra with [[Gene Kelly]]. 

He initially developed problems with his vocal cords during the comeback due to a prolonged period without singing.{{sfn|Sinatra|1986|p=233}} That Christmas, he performed at the [[Sahara Hotel]] in Las Vegas,{{sfn|Sinatra|1986|p=234}} and returned to Caesars Palace the following month in January 1974.{{sfn|Kelley|1986|p=436}} He began what Barbara Sinatra describes as a "massive comeback tour of the United States, Europe, the Far East, and Australia."{{sfn|Sinatra|2011|p=135}} In July, while on a second tour of Australia,{{sfn|Sinatra|1986|p=237}} he caused an uproar by describing journalists there{{snd}}who were aggressively pursuing his every move and pushing for a press conference{{snd}}as "bums, parasites, fags, and buck-and-a-half hookers."{{sfn|Sinatra|2011|p=136}} After he was pressured to apologize, Sinatra instead insisted that the journalists apologize for "fifteen years of abuse I have taken from the world press." Union actions canceled concerts and grounded Sinatra's plane, essentially trapping him in Australia.{{sfn|Kelley|1986|p=464}} 

Sinatra's lawyer, Mickey Rudin, arranged for Sinatra to issue a written conciliatory note and a final concert that was televised to the nation.{{sfn|Sinatra|1986|p=238}} In October 1974, he appeared at New York City's [[Madison Square Garden]] in a televised concert that was later released as an album under the title ''[[The Main Event&nbsp;– Live]]''. Backing him was bandleader [[Woody Herman]] and the Young Thundering Herd, who accompanied Sinatra on a European tour later that month.{{Sfn|Ackelson|1992|p=416}}<ref>{{cite book|title=Heritage Auctions Music and Entertainment Auction Catalog #696 – The Jilly Rizzo Estate Archive|url=https://books.google.com/books?id=1ko8xoiFxZwC&pg=PA46|date=September 1, 2008|publisher=Heritage Capital Corporation|isbn=978-1-59967-288-5|page=46|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429114219/https://books.google.com/books?id=1ko8xoiFxZwC&pg=PA46|url-status=live}}</ref>

In 1975, Sinatra performed in concerts in New York with Count Basie and [[Ella Fitzgerald]], and at the [[London Palladium]] with Basie and [[Sarah Vaughan]], and in Tehran [[Frank Sinatra: Live at Aryamehr Stadium|at Aryamehr Stadium]], giving 140 performances in 105 days.{{sfn|Sinatra|1986|p=245}} In August he held several concerts at [[Lake Tahoe]] together with the newly risen singer [[John Denver]],<ref>{{cite magazine|magazine=Billboard|title=Denver-Sinatra Superb Contrast at Lake Tahoe|first=Eliot|last=Tiegel|url=https://books.google.com/books?id=aBEEAAAAMBAJ&pg=PA1|date=August 16, 1975|page=1|issn=0006-2510|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429140104/https://books.google.com/books?id=aBEEAAAAMBAJ&pg=PA1|url-status=live}}</ref>{{Sfn|Fleischer|1976|p=46}} who became a frequent collaborator.<ref>{{cite web|author=Chilton, Martin|url=https://www.telegraph.co.uk/culture/music/music-news/9972507/John-Denver-gets-a-modern-makeover.html|title=John Denver gets a modern makeover|work=The Telegraph|date=April 6, 2006|access-date=October 1, 2015|archive-date=October 6, 2015|archive-url=https://web.archive.org/web/20151006002803/http://www.telegraph.co.uk/culture/music/music-news/9972507/John-Denver-gets-a-modern-makeover.html|url-status=live}}</ref> Sinatra had recorded Denver's "[[Leaving on a Jet Plane]]" and "[[My Sweet Lady]]" for ''[[Sinatra & Company]]'' (1971),{{sfn|Bogdanov|Woodstra|Erlewine|2002|p=1171}}<ref>{{cite web|url=http://www.allmusic.com/album/sinatra-company-mw0000318860|title=Sinatra & Company|website=AllMusic|access-date=October 8, 2015|archive-date=October 12, 2015|archive-url=https://web.archive.org/web/20151012081944/http://www.allmusic.com/album/sinatra-company-mw0000318860|url-status=live}}</ref> and according to Denver, his song "A Baby Just Like You" was written at Sinatra's request for his new grandchild, Angela.{{sfn|Denver|2002|p=28}} 

During the Labor Day weekend held in 1976, Sinatra was responsible for reuniting old friends and comedy partners Dean Martin and [[Jerry Lewis]] for the first time in nearly twenty years, when they performed at the "[[Jerry Lewis MDA Telethon]]".{{Sfn|Moser|2011|p=1959}}<ref>{{cite web|url=http://www.nydailynews.com/entertainment/tv/jerry-lewis-telethon-ends-decades-long-run-mda-article-1.2207512|title=Jerry Lewis telethon ends decades-long run, fundraising awareness for Muscular Dystrophy Association|work=Daily News|date=May 2, 2015|access-date=October 1, 2015|archive-date=October 2, 2015|archive-url=https://web.archive.org/web/20151002055339/http://www.nydailynews.com/entertainment/tv/jerry-lewis-telethon-ends-decades-long-run-mda-article-1.2207512|url-status=live}}</ref> That year, the [[New York Friars Club|Friars Club]] selected him as the "Top Box Office Name of the Century", and he was given the Scopus Award by the American Friends of the [[Hebrew University of Jerusalem]] in Israel and an honorary Doctor of Humane Letters from the [[University of Nevada, Las Vegas|University of Nevada]].{{sfn|Sinatra|1986|p=245}}

Sinatra continued to perform at Caesars Palace in the late 1970s and was performing there in January 1977 when his mother Dolly died in a plane crash on the way to see him.{{sfnm|1a1=Goldstein|1y=1982|1p=123|2a1=Turner|2y=2004|2p=173}}<ref name="mdtgsi">{{cite news |url=https://news.google.com/newspapers?id=CPpLAAAAIBAJ&pg=4998%2C1870220 |work=Spokane Daily Chronicle |location=(Washington) |agency=Associated Press |title=Mother's death grieves Sinatra |date=January 10, 1977 |page=2 |access-date=October 17, 2020 |archive-date=October 30, 2021 |archive-url=https://web.archive.org/web/20211030014853/https://news.google.com/newspapers?id=CPpLAAAAIBAJ&pg=4998%2C1870220 |url-status=live }}</ref> He canceled two weeks of shows and spent time recovering from the shock in Barbados.{{sfn|Sinatra|2011|p=201}} In March, he performed in front of [[Princess Margaret]] at the [[Royal Albert Hall]] in London, raising money for the [[National Society for the Prevention of Cruelty to Children]].{{sfn|Sinatra|1986|p=261}} On March 14, he recorded with Nelson Riddle for the last time, recording the songs "[[Linda (1946 song)|Linda]]", "Sweet Lorraine", and "Barbara".{{sfn|Granata|2003|p=192}} The two men had a major falling out and later patched up their differences in January 1985 at a dinner organized for Ronald Reagan when Sinatra asked Riddle to make another album with him. Riddle was ill at the time and died that October before they had a chance to record.{{sfn|Granata|2003|p=200}}

In 1978, Sinatra filed a $1{{nbsp}}million lawsuit against a land developer for using his name in the "Frank Sinatra Drive Center" in West Los Angeles.<ref>{{cite news|url=https://www.newspapers.com/clip/3405266/sinatra_sues_for_1_million/|title=Sinatra Sues for $1 Million|work=The Sanbernardino Sun ([[San Bernardino, California]])|date=January 21, 1978|page=17|access-date=October 12, 2015|via=[[Newspapers.com]]|archive-date=January 27, 2016|archive-url=https://web.archive.org/web/20160127052824/https://www.newspapers.com/clip/3405266/sinatra_sues_for_1_million/|url-status=live}} {{Open access}}</ref> During a party at Caesars in 1979, he was awarded the [[Grammy Trustees Award]], while celebrating 40 years in show business and his 64th birthday.{{sfn|Kelley|1986|p=505}}<ref>{{cite web | url=https://www.grammy.org/recording-academy/awards/trustee-awards | title=Trustees Award | publisher=[[Grammy Award|Grammy.org]] | access-date=October 1, 2015 | url-status=dead | archive-url=https://web.archive.org/web/20151002091150/https://www.grammy.org/recording-academy/awards/trustee-awards | archive-date=October 2, 2015 | df=mdy-all }}</ref> That year, former President [[Gerald Ford]] awarded Sinatra the [[American Biographical Institute|International Man of the Year Award]],{{sfn|Sinatra|1986|p=309}} and he performed in front of the [[Egyptian pyramids]] for [[Anwar Sadat]], which raised more than $500,000 for [[Jehan Sadat|Sadat's wife]]'s charities.{{sfn|Sinatra|1986|p=261}}

In 1980, Sinatra's first album in six years was released, ''[[Trilogy: Past Present Future]]'', a highly ambitious triple album that features an array of songs from both the pre-rock and rock eras.<ref name="Trilogy">{{cite web|url=http://www.allmusic.com/album/trilogy-past-present-future-mw0000197932/awards|title=Trilogy: Past, Present & Future&nbsp;– Awards|website=AllMusic|access-date=October 4, 2015|archive-date=October 7, 2015|archive-url=https://web.archive.org/web/20151007140105/http://www.allmusic.com/album/trilogy-past-present-future-mw0000197932/awards|url-status=live}}</ref> It was the first studio album of Sinatra's to feature his touring pianist at the time, Vinnie Falcone, and was based on an idea by [[Sonny Burke]].{{sfn|Granata|2003|pp=192–193}} The album garnered six [[Grammy]] nominations{{nbsp}}– winning for best liner notes{{nbsp}}– and peaked at number 17 on ''Billboard''{{'}}s album chart,<ref name="Trilogy" /> and spawned yet another song that would become a signature tune, "[[Theme from New York, New York]]".{{sfn|Granata|2003|p=192}} 

That year, as part of the Concert of the Americas, he performed in the [[Maracanã Stadium]] in [[Rio de Janeiro]], Brazil, which broke records for the "largest live paid audience ever recorded for a solo performer".{{sfn|Sinatra|1986|p=310}} The following year, Sinatra built on the success of ''Trilogy'' with ''[[She Shot Me Down]]'', an album that was praised for embodying the dark tone of his Capitol years.<ref name="She Shot Me Down">"[{{AllMusic|class=album|id=r26337|pure_url=yes}} ''She Shot Me Down'']. AllMusic. Retrieved November 28, 2006.</ref> Also in 1981, Sinatra was embroiled in controversy when he worked a 10-day engagement for $2{{nbsp}}million in [[Sun City, North West|Sun City]], in the internationally unrecognized [[Bophuthatswana]], breaking a cultural boycott against apartheid-era South Africa. President [[Lucas Mangope]] awarded Sinatra with the highest honor, the Order of the Leopard, and made him an honorary tribal chief.{{sfn|Lamb|2011|p=328}}

=== 1982–1998: Later career and final projects ===
[[File:Fremont street 1983.jpg|thumb|left|Sinatra signed a $16{{nbsp}}million three-year deal with the [[Golden Nugget Las Vegas]] in 1982.]]
[[File:Handprint of Frank Sinatra.jpg|thumb|Handprint of Sinatra. Atlantic City Boardwalk, New Jersey, US, 2006]]
Santopietro stated that by the early 1980s, Sinatra's voice had "coarsened, losing much of its power and flexibility, but audiences didn't care."{{sfn|Santopietro|2008|p=431}} In 1982, he signed a $16{{nbsp}}million three-year deal with the [[Golden Nugget Las Vegas|Golden Nugget]] of Las Vegas. 

Kelley notes that by this period, Sinatra's voice had grown "darker, tougher and loamier", but he "continued to captivate audiences with his immutable magic." She added that his baritone voice "sometimes cracked, but the gliding intonations still aroused the same raptures of delight as they had at the Paramount Theater."{{sfn|Kelley|1986|p=540}} 

That year, he made a reported further $1.3{{nbsp}}million from the Showtime television rights to his "Concert of the Americas" in the Dominican Republic, $1.6{{nbsp}}million for a concert series at [[Carnegie Hall]], and $250,000 in just one evening at the Chicago Fest. He donated a lot of his earnings to charity.{{sfn|Kelley|1986|p=542}} He put on a performance at the White House for Italian president [[Sandro Pertini]], and performed at the [[Radio City Music Hall]] with [[Luciano Pavarotti]] and [[George Shearing]].{{sfn|Sinatra|1986|p=311}}<ref>{{cite news|url=https://www.washingtonpost.com/archive/lifestyle/1982/03/26/romans-holiday/844354a7-5981-4b46-97d6-c71ea0a9a7cc/|title=Roman's Holiday|newspaper=The Washington Post|date=March 26, 1982|access-date=March 19, 2024}}</ref>

Sinatra was honored at the 1983 [[Kennedy Center Honors]], alongside [[Katherine Dunham]], [[James Stewart]], [[Elia Kazan]], and [[Virgil Thomson]]. Quoting [[Henry James]], President Reagan said in honoring his old friend that "art was the shadow of humanity" and that Sinatra had "spent his life casting a magnificent and powerful shadow."{{sfn|Kelley|1986|p=544}} 

On September 21, 1983, Sinatra filed a $2{{nbsp}}million court case against [[Kitty Kelley]], suing her for punitive damages, before her unofficial biography, ''His Way'', was even published. The book became a best-seller for "all the wrong reasons" and "the most eye-opening [[celebrity biographer|celebrity biography]] of our time", according to [[William Safire]] of ''The New York Times''.<ref name="ESSAY">{{cite news|author=Safire, William|url=https://www.nytimes.com/1986/09/29/opinion/essay-the-truth-about-frank.html|title=Essay: The Truth About Frank|work=The New York Times|date=September 19, 1986|access-date=September 30, 2015|archive-date=October 11, 2015|archive-url=https://web.archive.org/web/20151011023908/http://www.nytimes.com/1986/09/29/opinion/essay-the-truth-about-frank.html|url-status=live}}</ref> Sinatra was always adamant that such a book would be written on his terms, and he himself would "set the record straight" in details of his life.{{sfn|Kelley|1986|p=Author's note xvii}} 

According to Kelley, the family detested her and the book, which took its toll on Sinatra's health. Kelley says that Tina Sinatra blamed her for her father's colon surgery in 1986.{{sfn|Kelley|1986|p=Introduction xv}} He was forced to drop the case on September 19, 1984, with several leading newspapers expressing concerns about censorship.{{sfn|Kelley|1986|p=Author's note xviii}}

In 1984, Sinatra worked with Quincy Jones for the first time in nearly two decades on the album ''[[L.A. Is My Lady]]'', which was well received critically.{{sfn|Turner|2004|p=188}} The album was a substitute for another Jones project, an album of duets with [[Lena Horne]], which had to be abandoned.{{efn|Horne developed vocal problems, and Sinatra, committed to other engagements, could not wait to record.{{sfn|Gavin|2009|p=444}}}} In 1986, Sinatra collapsed on stage while performing in [[Atlantic City]] and was hospitalized for [[diverticulitis]],{{sfn|Rojek|2004|p=55}} which left him looking frail.{{sfn|Santopietro|2008|p=442}} Two years later, Sinatra reunited with Martin and Davis and went on the Rat Pack Reunion Tour, during which they played many large arenas. When Martin dropped out of the tour early on, a rift developed between them, and the two never spoke again.{{sfn|Santopietro|2008|p=444}}

On June 6, 1988, Sinatra made his last recordings with Reprise for an album that was not released. He recorded "[[My Foolish Heart (song)|My Foolish Heart]]", "[[Cry Me a River (1953 song)|Cry Me a River]]", and other songs. Sinatra never completed the project, but take number 18 of "My Foolish Heart" may be heard in ''[[The Complete Reprise Studio Recordings]]'' (1995).<ref>{{Cite web|url=http://www.newzbreaker.com/2016/08/30/foolish-heart-the-lost-albums-of-frank-sinatra/|title=Foolish Heart: The Lost Albums of Frank Sinatra |website=Newz Breaker|first=Jerry|last=Pearce|date=August 30, 2016 |access-date=July 10, 2017|archive-date=September 11, 2017|archive-url=https://web.archive.org/web/20170911205647/http://www.newzbreaker.com/2016/08/30/foolish-heart-the-lost-albums-of-frank-sinatra/|url-status=live}}</ref>

[[File:Brendan Grace with Frank Sinatra.JPG|thumb|[[Brendan Grace]] and Sinatra in 1991]]
In 1990, Sinatra was awarded the second "Ella Award" by the Los Angeles-based [[Society of Singers]], and performed for a final time with Ella Fitzgerald at the award ceremony.{{sfn|Levinson|2001|p=159}} Sinatra maintained an active touring schedule in the early 1990s, performing 65 concerts in 1990, 73 in 1991, and 84 in 1992 in seventeen countries.{{sfn|Santopietro|2008|p=448}}

In 1993, Sinatra returned to Capitol Records and the recording studio for ''[[Duets (Frank Sinatra album)|Duets]]'', which became his best-selling album.{{sfn|Santopietro|2008|p=451}} The album and its sequel, ''[[Duets II (Frank Sinatra album)|Duets II]]'', released the following year,{{sfn|Santopietro|2008|p=452}} would see Sinatra remake his classic recordings with popular contemporary performers, who added their vocals to a pre-recorded tape.{{sfn|Cole|Browning|Schroeder|2003|p=28}}

During his tours in the early 1990s, his memory failed him at times during concerts, and he fainted onstage in [[Richmond, Virginia]] in March 1994.{{sfn|Friedwald|1995|p=445}} His final public concerts were held in [[Fukuoka Dome]] in Japan on December 19–20, 1994.{{sfn|Turner|2004|p=196}} The following year, Sinatra sang for the last time on February 25, 1995, before a live audience of 1200 select guests at the Palm Desert Marriott Ballroom on the closing night of the Frank Sinatra Desert Classic golf tournament.{{sfnm|1a1=Santopietro|1y=2008|1p=452|2a1=Sinatra|2y=2011|2p=274}} 

''[[Esquire (magazine)|Esquire]]'' reported of the show that Sinatra was "clear, tough, on the money" and "in absolute control".{{sfn|Ingham|2005|p=104}} Sinatra was awarded the [[Grammy Legend Award|Legend Award]] at the [[1994 Grammy Awards]], where he was introduced by [[Bono]], who said of him, "Frank's the chairman of the bad attitude{{nbsp}}... Rock 'n roll plays at being tough, but this guy is the boss{{nbsp}}– the chairman of boss".<ref name="bono">{{cite web|url=http://www.mtv.com/news/1434089/bono-on-sinatras-legacy/|title=Bono On Sinatra's Legacy|publisher=MTV|date=May 15, 1998|access-date=August 17, 2015|archive-date=October 2, 2015|archive-url=https://web.archive.org/web/20151002232251/http://www.mtv.com/news/1434089/bono-on-sinatras-legacy/|url-status=dead}}</ref><ref>{{cite news|title=Top Grammy to Houston; 5 for 'Aladdin{{'-}}|url=https://www.nytimes.com/1994/03/02/movies/top-grammy-to-houston-5-for-aladdin.html|date=March 2, 1994|first=Jon|last=Pareles|work=The New York Times|access-date=February 15, 2012|archive-date=June 2, 2009|archive-url=https://web.archive.org/web/20090602224016/http://www.nytimes.com/1994/03/02/movies/top-grammy-to-houston-5-for-aladdin.html|url-status=live}}</ref>

In 1995, to mark Sinatra's 80th birthday, the [[Empire State Building]] glowed blue.<ref name="Guides2014">{{cite book|title=Insight Guides: New York City Guide&nbsp;– Illuminated Display|url=https://books.google.com/books?id=K7UxBgAAQBAJ&pg=PT323|date=November 6, 2014|publisher=APA|isbn=978-1-78005-837-5|page=323|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429135725/https://books.google.com/books?id=K7UxBgAAQBAJ&pg=PT323|url-status=live}}</ref> A star-studded birthday tribute, ''Sinatra: 80 Years My Way'', was held at the [[Shrine Auditorium]] in Los Angeles, featuring performers such as [[Ray Charles]], [[Little Richard]], [[Natalie Cole]] and [[Salt-N-Pepa]] singing his songs.{{sfn|Kelley|1986|p=Introduction x}} At the end of the program, Sinatra performed on stage for the last time to sing the final notes of the "Theme from New York, New York" with an ensemble.<ref>{{cite web|url=https://variety.com/1995/tv/reviews/sinatra-80-years-my-way-1200444080/|title=Review: 'Sinatra: 80 Years My Way'|work=Variety|first=Phil|last=Gallo|date=December 13, 1995|access-date=October 2, 2015|archive-date=October 3, 2015|archive-url=https://web.archive.org/web/20151003154808/http://variety.com/1995/tv/reviews/sinatra-80-years-my-way-1200444080/|url-status=live}}</ref> In recognition of his many years of association with Las Vegas, Sinatra was elected to the [[Gaming Hall of Fame]] in 1997.<ref>{{cite web|title=The Gaming Hall of Fame|url=http://gaming.unlv.edu/hof/index.html|publisher=[[University of Nevada, Las Vegas]]|access-date=August 30, 2009|archive-date=March 18, 2012|archive-url=https://web.archive.org/web/20120318103112/http://gaming.unlv.edu/hof/index.html|url-status=live}}</ref>

== Artistry ==
{{anchor|Sinatra, the musician}}
[[File:(Portrait of Frank Sinatra and Axel Stordahl, Liederkrantz Hall, New York, N.Y., ca. 1947) (LOC) (4843758568).jpg|thumb|left|upright|Sinatra with Axel Stordahl at the Liederkrantz Hall in New York, {{circa|1947}}]]
While Sinatra never learned how to read music well, he had a natural understanding of it,{{sfn|Lees|1998|p=102}} and he worked very hard from a young age to improve his abilities in all aspects of music.{{sfn|Sinatra|1986|p=31}} He could follow a [[lead sheet]] (simplified sheet music showing a song's basic structure) during a performance by "carefully following the patterns and groupings of notes arranged on the page" and made his own notations to the music, using his ear to detect semitonal differences.{{sfn|Granata|2003|p=38}} 

Granata states that some of the most accomplished classically trained musicians soon noticed his musical understanding and remarked that Sinatra had a "sixth sense", which "demonstrated unusual proficiency when it came to detecting incorrect notes and sounds within the orchestra."{{sfn|Granata|2003|p=30}} 

Sinatra was an aficionado of classical music,{{sfn|Friedwald|1995|p=21}} and would often request classical strains in his music, inspired by composers such as [[Puccini]] and [[Impressionism in music|Impressionist]] masters. His personal favorite was [[Ralph Vaughan Williams]].{{sfn|Granata|2003|p=93}} He would insist on always recording live with the band because it gave him a "certain feeling" to perform live surrounded by musicians.{{sfn|Granata|2003|p=112}}
By the mid-1940s, such was his understanding of music that after hearing an [[air check]] of some compositions by [[Alec Wilder]], which were for strings and woodwinds, he became the conductor at Columbia Records for six of Wilder's compositions.{{efn|Mitch Miller played English horn and oboe on the Sinatra-led recordings.{{sfn|Lees|1998|p=102}}}} The works were considered by Wilder to have been among the finest renditions and recordings of his compositions, past or present.{{sfn|Lees|1998|p=102}} Critic Gene Lees, a lyricist and the author of the words to the Jobim melody "This Happy Madness", expressed amazement when he heard Sinatra's recording of it on ''[[Sinatra & Company]]'' (1971), considering him to have delivered the lyrics to perfection.{{sfn|Lees|1998|pp=102–103}}

Voice coach John Quinlan was impressed by Sinatra's vocal range, remarking, "He has far more voice than people think he has. He can vocalize to a B-flat on top in full voice, and he doesn't need a mic either".{{sfn|Kelley|1986|p=45}} As a singer, early on, he was primarily influenced by Bing Crosby,{{sfn|Lahr|2000|p=56}} but later believed that [[Tony Bennett]] was "the best singer in the business."{{sfn|Sinatra|2011|p=98}} Bennett himself claimed that as a performer, Sinatra had "perfected the art of intimacy."<ref>{{Cite journal|title = The Frank Sinatra Reader|last = White|first = John|year = 1996|journal = Journal of American Studies}}</ref> According to Nelson Riddle, Sinatra had a "fairly rangy voice", {{efn|Riddle notes that Sinatra's range was from the low G to the high F, almost two octaves, but that his practical range was the low A-flat to a D, in comparison to Bing Crosby whose range was G to C.{{sfn|Granata|2003|p=11}} Though Riddle stated that Sinatra's lowest was G, he often hit the low F in concerts and hit the low E at 0:41 in the recording of "[[What Is This Thing Called Love?]]" for the 1955 album ''In the Wee Small Hours''.}} remarking that "His voice has a very strident, insistent sound in the top register, a smooth lyrical sound in the middle register, and a very tender sound in the low. His voice is built on infinite taste, with an overall inflection of sex. He points everything he does from a sexual standpoint".{{sfn|Granata|2003|p=11}} 

Despite his heavy New Jersey accent, when Sinatra sang, his accent was barely detectable;{{sfn|Kelley|1986|loc=p. 66: {{" '}}Frank sang beautifully, but he spoke with "deze, dem, and doze" diction&nbsp;... He had a terrible New Jersey accent, but it didn't show in his singing{{' "}}}} according to Richard Schuller, his diction became "precise" while singing and his articulation "meticulous".{{sfn|Granata|2003|p=11}} His timing was impeccable, allowing him, according to Charles L. Granata, to "toy with the rhythm of a melody, bringing tremendous excitement to his reading of a lyric."{{sfn|Granata|2003|p=13}} Tommy Dorsey observed that Sinatra would "take a musical phrase and play it all the way through seemingly without breathing for eight, ten, maybe sixteen bars." Dorsey was a considerable influence on Sinatra's techniques for his vocal phrasing with his own exceptional breath control on the trombone,{{sfn|Lees|1998|pp=95–96}} and Sinatra regularly swam and held his breath underwater, thinking of song lyrics to increase his breathing power.{{sfn|Lahr|2000|pp=59–60}}
{{quote box|width=30em|bgcolor=#c6dbf7|align=left|quote="He'd always been critical of his voice, and that only intensified as he got older. He never liked to discuss a performance afterward because he knew his voice wasn't as good as it used to be. If someone told him he'd been great, he'd reply, 'It was a nice crowd, but my reed was off' or 'I wasn't so good on the third number.' Strangely, in spite of his hearing problems, he had the most incredible ear, which often drove those he worked with nuts. There could be an orchestra of a hundred musicians, and if one played a bum note, he'd know exactly who was responsible."|source=—Barbara Sinatra on Sinatra's voice and musical understanding.{{sfn|Sinatra|2011|p=240}}}}
Arrangers such as Nelson Riddle and Anthony Fanzo found Sinatra to be a perfectionist who constantly drove himself and others around him, stating that his collaborators approached him with uneasiness because of his unpredictable and often volatile temperament.{{sfn|Kelley|1986|p=234}} 

Granata comments that Sinatra was almost fanatically obsessed with perfection to the point that people began wondering if he was genuinely concerned about the music or showing off his power over others.{{sfn|Granata|2003|p=50}} On days when he felt that his voice was not right, he would know after only a few notes and would postpone the recording session until the following day, yet still pay his musicians.{{sfn|Granata|2003|p=105}} 

After a period of performing, Sinatra tired of singing a certain set of songs and was always looking for talented new songwriters and composers to work with. Once he found ones that he liked, he actively sought to work with them as often as he could and made friends with many of them. Over the years, he recorded 87 of [[Sammy Cahn]]'s songs, of which 24 were composed by [[Jule Styne]] and 43 by Jimmy Van Heusen. The Cahn-Styne partnership lasted from 1942 until 1954, when Van Heusen succeeded him as Sinatra's main composer.{{sfn|Granata|2003|pp=14–16}}

Unlike many of his contemporaries, Sinatra insisted upon direct input regarding arrangements and tempos for his recordings. He would spend weeks thinking about the songs he wanted to record and would keep an arranger in mind for each song.{{sfn|Friedwald|1995|pp=28–29}} Barbara Sinatra notes that Sinatra would almost always credit the songwriter at the end of each number and would often make comments to the audience, such as "Isn't that a pretty ballad" or "Don't you think that's the most marvelous love song", delivered with "childlike delight".{{sfn|Sinatra|2011|p=140}} She states that after each show, Sinatra would be "in a buoyant, electrically charged mood, a post-show high that would take him hours to come down from as he quietly relived every note of the performance he'd just given."{{sfn|Sinatra|2011|p=142}}
{{quote box|width=30em|bgcolor=#c6dbf7|align=right|quote="His voice is more interesting now: he has separated his voice into different colors, in different registers. Years ago, his voice was more even, and now it is divided into at least three interesting ranges: low, middle, and high. [He's] probing more deeply into his songs than he used to. That may be due to the ten years he's put on and the things he's been through."|source=—Nelson Riddle noting the development of Sinatra's voice in 1955.{{sfn|Granata|2003|p=137}}}}
Sinatra's split with Gardner in the fall of 1953 had a profound impact on the types of songs he sang and on his voice. He began to console himself in songs with a "brooding melancholy", such as "[[I'm a Fool to Want You]]", "[[Don't Worry 'Bout Me]]", "[[My One and Only Love]]" and "[[There Will Never Be Another You]]",{{sfn|Kelley|1986|p=232}} which Riddle believed was the direct influence of Ava Gardner. 

Lahr comments that the new Sinatra was "not the gentle boy balladeer of the forties. Fragility had gone from his voice, to be replaced by a virile adult's sense of happiness and hurt".{{sfn|Lahr|2000|p=69}} Author Granata considered Sinatra a "master of the art of recording", noting that his work in the studio "set him apart from other gifted vocalists." During his career, he made over 1000 recordings.{{sfn|Granata|2003|pp=xiii–xvi}} Recording sessions would typically last three hours. However, Sinatra would always prepare for them by spending at least an hour by the piano beforehand to vocalize, followed by a short rehearsal with the orchestra to ensure the balance of sound.{{sfn|Granata|2003|p=36}} 

During his Columbia years, Sinatra used an [[RCA Type 44]] microphone, which Granata describes as "the 'old-fashioned' microphone which is closely associated with Sinatra's crooner image of the 1940s".{{sfn|Granata|2003|p=37}} At Capitol, he used a [[Neumann U 47]], an "ultra-sensitive" microphone that better captured the timbre and tone of his voice.{{sfn|Granata|2003|pp=111–112}}

In the 1950s, Sinatra's career was facilitated by developments in technology. Up to sixteen songs could now be held by the twelve-inch L.P., and this allowed Sinatra to use song in a novelistic way, turning each track into a kind of chapter, which built and counterpointed moods to illuminate a larger theme".{{sfn|Lahr|2000|pp=69–70}} Santopietro writes that through the 1950s and well into the 1960s, "Every Sinatra LP was a masterpiece of one sort of another, whether uptempo, torch song, or swingin' affairs. Track after track, the brilliant concept albums redefined the nature of pop vocal art".{{Sfn|Santopietro|2008|p=239}}

== Film career ==
{{See also|Frank Sinatra filmography}}

=== 1941–1952: Debut, musical films, and career slump ===
Sinatra attempted to pursue an acting career in Hollywood in the early 1940s. While films appealed to him,{{Sfn|Young|Young|2010|p=635}} being exceptionally self-confident,{{sfn|Santopietro|2008|p=6}} he was rarely enthusiastic about his own acting, once remarking that "pictures stink".{{sfn|Santopietro|2008|p=57}} Sinatra made his film debut performing in an uncredited sequence in ''[[Las Vegas Nights]]'' (1941), singing "I'll Never Smile Again" with Tommy Dorsey's Pied Pipers.<ref>{{cite magazine|magazine=Billboard|title=Jazzmen Have Always Favored FS|url=https://books.google.com/books?id=EwkEAAAAMBAJ&pg=PA44|date=November 24, 1973|page=44|first=Leonard|last=Feather|issn=0006-2510|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429073015/https://books.google.com/books?id=EwkEAAAAMBAJ&pg=PA44|url-status=live}}</ref> He had a cameo role along with Duke Ellington and Count Basie in [[Charles Barton (director)|Charles Barton]]'s ''[[Reveille with Beverly]]'' (1943), making a brief appearance singing "[[Night and Day (song)|Night and Day]]".{{sfn|Knight|2010|p=80}} Next, he was given leading roles in ''[[Higher and Higher (film)|Higher and Higher]]'' and ''[[Step Lively (1944 film)|Step Lively]]'' (both 1944) for [[RKO Pictures|RKO]].{{sfn|Knight|2010|p=16, 20}}<ref>{{cite news|url=https://www.nytimes.com/movie/review?res=9900E6DC1030E53BBC4A51DFB766838F659EDE|title=Lower and Lower|work=The New York Times|first=Bosley|last=Crowther|date=January 22, 1944|access-date=August 31, 2015|archive-date=September 26, 2015|archive-url=https://web.archive.org/web/20150926065808/http://www.nytimes.com/movie/review?res=9900E6DC1030E53BBC4A51DFB766838F659EDE|url-status=live}}</ref>

[[File:Anchors Aweigh promo still (Sinatra and Kelly dancing).jpg|thumb|upright|alt=Black-and-white photograph of two dancing men in sailor suits|Sinatra and [[Gene Kelly]] in ''[[Anchors Aweigh (film)|Anchors Aweigh]]'' (1945)]]
[[Metro-Goldwyn-Mayer]] cast Sinatra opposite [[Gene Kelly]] and [[Kathryn Grayson]] in the [[Technicolor]] musical ''[[Anchors Aweigh (film)|Anchors Aweigh]]'' (1945), in which he played a sailor on leave in Hollywood.{{sfn|Knight|2010|p=29}}<ref>{{cite news | url=https://www.nytimes.com/movie/review?res=9F0DE3DC103BEE3BBC4851DFB166838E659EDE | title='Anchors Aweigh', Gay Musical Film, With Gene Kelly, Frank Sinatra and Miss Grayson, Opens at the Capitol Theatre | work=The New York Times | date=July 20, 1945 | author=Crowther, Bosley | access-date=October 5, 2015 | archive-date=January 29, 2016 | archive-url=https://web.archive.org/web/20160129180054/http://www.nytimes.com/movie/review?res=9F0DE3DC103BEE3BBC4851DFB166838E659EDE | url-status=live }}</ref> A major success,{{sfn|Knight|2010|p=32}} it garnered several Academy Award wins and nominations, and the song "[[I Fall in Love Too Easily]]", sung by Sinatra in the film, was nominated for the [[Academy Award for Best Original Song]].<ref>{{cite web | url=https://www.oscars.org/oscars/ceremonies/1946 | title=The 18th Academy Awards | publisher=Academy of Motion Picture Arts and Sciences | access-date=October 5, 2015 | archive-date=December 15, 2019 | archive-url=https://web.archive.org/web/20191215135117/https://oscars.org/oscars/ceremonies/1946 | url-status=live }}</ref> He briefly appeared at the end of [[Richard Whorf]]'s commercially successful ''[[Till the Clouds Roll By]]'' (1946), a Technicolor musical biopic of [[Jerome Kern]], in which he sang "[[Ol' Man River]]".{{sfnm|1a1=Green|1y=1999|1p=141|2a1=Santopietro|2y=2008|2p=81}}

Sinatra co-starred again with Gene Kelly in the Technicolor musical ''[[Take Me Out to the Ball Game (film)|Take Me Out to the Ball Game]]'' (1949), in which they play baseball players who are part-time vaudevillians.{{sfn|McGuiggan|2009|p=86}} He teamed up with Kelly for a third time in ''[[On the Town (film)|On the Town]]'' (1949), playing a sailor on leave in New York City. The film remains rated very highly by critics, and in 2006, it ranked No. 19 on the [[American Film Institute]]'s [[AFI's 100 Years of Musicals|list of best musicals]].<ref>{{cite web|url=http://www.afi.com/100years/musicals.aspx|title=AFI's 25 Greatest Movie Musicals of All Time|publisher=American Film Institute|access-date=August 31, 2015|archive-date=January 14, 2013|archive-url=https://web.archive.org/web/20130114195037/http://www.afi.com/100Years/musicals.aspx|url-status=live}}</ref> Both ''[[Double Dynamite]]'' (1951), an RKO [[Irving Cummings]] comedy produced by [[Howard Hughes]],{{sfn|Hernandez|2010|pp=287–288}} and [[Joseph Pevney]]'s ''[[Meet Danny Wilson (film)|Meet Danny Wilson]]'' (1952) failed to make an impression.{{sfnm|1a1=Santopietro|1y=2008|1pp=128–129|2a1=Knight|2y=2010|2p=77}}

=== 1953–1959: Career comeback and prime ===
{{multiple image
| align = left
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| image1 = Sinatra in From Here to Eternity (1953 publicity photo).jpg
| alt1 = 
| caption1 = {{resize|Sinatra as Maggio in ''[[From Here to Eternity]]''}}
| image2 = Frank Sinatra holding Oscar (1954-03-25).jpg
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| caption2 = {{resize|Sinatra at the [[26th Academy Awards]]}}
| footer = For his performance in ''From Here to Eternity'' (1953), Sinatra received the [[Academy Award for Best Supporting Actor]].}}
[[Fred Zinnemann]]'s ''[[From Here to Eternity]]'' (1953) deals with the tribulations of three soldiers, played by [[Burt Lancaster]], [[Montgomery Clift]], and Sinatra, stationed on [[Hawaii]] in the months leading up to the [[attack on Pearl Harbor]].{{sfn|Knight|2010|p=86}} Sinatra had long been desperate to find a film role that would bring him back into the spotlight, and Columbia Pictures boss [[Harry Cohn]] had been inundated by appeals from people across Hollywood to give Sinatra a chance to star as "Maggio" in the film.{{sfn|Kelley|1986|pp=210, 214}}{{efn|Sinatra successfully later sued a BBC interviewer who said that he'd used his Mafia connections to get the part.{{sfn|Kelley|1986|p=215}}}} During production, Montgomery Clift became a close friend,{{sfn|Wayne|2004|p=164}} and Sinatra later professed that he "learned more about acting from him than anybody I ever knew before".<ref>{{cite book|title=Out, Issues 82–85 – Sinatra on From Here to Eternity|url=https://books.google.com/books?id=dOXZAAAAMAAJ|date=September 2000|publisher=Out Pub., Incorporated|page=44|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429101252/https://books.google.com/books?id=dOXZAAAAMAAJ|url-status=live}}</ref> After several years of critical and commercial decline, his [[Academy Award for Best Supporting Actor]] win helped him regain his position as the top recording artist in the world.<ref>{{cite news|last=Schmidt|first=M.A.|url=https://www.nytimes.com/packages/html/movies/bestpictures/eternity-ar.html|title=Back on the High Road With a Busy Minstrel|work=The New York Times|date=May 9, 1954|access-date=August 31, 2015|archive-date=January 15, 2016|archive-url=https://web.archive.org/web/20160115181430/http://www.nytimes.com/packages/html/movies/bestpictures/eternity-ar.html|url-status=live}}</ref> His performance also won a [[Golden Globe Award for Best Supporting Actor – Motion Picture]].<ref name=GoldenGlobes>{{cite web | url=http://www.goldenglobes.com/frank-sinatra | title=Frank Sinatra at the Golden Globe Awards | publisher=[[Golden Globe Award]]s | access-date=October 7, 2015 | archive-url=https://web.archive.org/web/20150115021651/http://www.goldenglobes.com/frank-sinatra | archive-date=January 15, 2015}}</ref> The ''Los Angeles Examiner'' wrote that Sinatra is "simply superb, comical, pitiful, childishly brave, pathetically defiant", commenting that his death scene is "one of the best ever photographed".{{sfn|Kelley|1986|p=224}}

Sinatra starred opposite [[Doris Day]] in the musical film ''[[Young at Heart (1954 film)|Young at Heart]]'' (1954),<ref>{{cite news|url=https://www.nytimes.com/movie/review?res=9D04E3D7123AE53BBC4851DFB766838E649EDE|title=The Screen in Review; Doris Day and Sinatra Star at Paramount|work=The New York Times|date=January 20, 1955|author=Crowther, Bosley|access-date=October 5, 2015|archive-date=March 25, 2016|archive-url=https://web.archive.org/web/20160325014734/http://www.nytimes.com/movie/review?res=9D04E3D7123AE53BBC4851DFB766838E649EDE|url-status=live}}</ref> and earned critical praise for his performance as a psychopathic killer posing as an [[FBI]] agent opposite [[Sterling Hayden]] in the [[film noir]] ''[[Suddenly (1954 film)|Suddenly]]'' (1954).{{sfn|Santopietro|2008|pp=147–148}}

Sinatra was nominated for an [[Academy Award for Best Actor]] and [[BAFTA Award for Best Actor in a Leading Role]] for his role as a heroin addict in ''[[The Man with the Golden Arm]]'' (1955).{{sfn|Geraghty|2011|p=18}}{{efn|Sinatra later remarked that he had always considered his performance in ''The Man with the Golden Arm'' to have been the greatest of his film career and that he'd won the Oscar for the wrong role.{{Sfn|Santopietro|2008|p=195}}}} After roles in ''[[Guys and Dolls (film)|Guys and Dolls]]'',{{Sfn|Santopietro|2008|pp=168–170}} and ''[[The Tender Trap (film)|The Tender Trap]]'' (both 1955),{{sfnm|1a1=Turner|1y=2004|1p=93|2a1=Santopietro|2y=2008|2p=175}} Sinatra was nominated for a BAFTA Award for Best Actor in a Leading Role for his role as a medical student in [[Stanley Kramer]]'s directorial début, ''[[Not as a Stranger]]'' (1955).{{sfnm|1a1=Knight|1y=2010|1p=110|2a1=Epstein|2y=2013|2p=98}} During production, Sinatra got drunk with [[Robert Mitchum]] and [[Broderick Crawford]] and trashed Kramer's dressing room.{{sfn|Kelley|1986|p=257}} Kramer vowed at the time never to hire Sinatra again and later regretted casting him as a Spanish guerrilla leader in ''[[The Pride and the Passion]]'' (1957).{{sfn|Hickey|2015|p=76}}<ref>{{cite journal|title=New York Magazine&nbsp;– Television Highlights|website=Newyorkmetro.com|url=https://books.google.com/books?id=M-MCAAAAMBAJ&pg=PA85|date=September 7, 1992|page=85|issn=0028-7369|access-date=October 20, 2015|archive-date=April 25, 2016|archive-url=https://web.archive.org/web/20160425232330/https://books.google.com/books?id=M-MCAAAAMBAJ&pg=PA85|url-status=live}}</ref>

[[File:Grace Kelly Frank Sinatra on the set of High Society 1956.jpg|thumb|Sinatra with [[Grace Kelly]] on the set of ''[[High Society (1956 film)|High Society]]'' (1956)]]
Sinatra featured alongside [[Bing Crosby]] and [[Grace Kelly]] in ''[[High Society (1956 film)|High Society]]'' (1956) for MGM, earning a reported $250,000 for the picture.{{sfn|Santopietro|2008|p=203}} The public rushed to the cinemas to see Sinatra and Crosby together on-screen, and it ended up earning over $13{{nbsp}}million at the box office, becoming one of the highest-grossing pictures of its year.{{sfn|Knight|2010|p=136}} He starred opposite [[Rita Hayworth]] and [[Kim Novak]] in [[George Sidney]]'s ''[[Pal Joey (film)|Pal Joey]]'' (1957), for which Sinatra won a [[Golden Globe Award for Best Actor&nbsp;– Motion Picture Musical or Comedy]].<ref name=GoldenGlobes /> Santopietro considers the scene in which Sinatra sings "[[The Lady Is a Tramp]]" to have been the finest moment of his film career.{{sfn|Santopietro|2008|pp=235–236}} He next portrayed comedian [[Joe E. Lewis]] in ''[[The Joker Is Wild]]'' (1957);{{sfn|O'Brien|2014|p=221}} the song "[[All the Way (Frank Sinatra song)|All the Way]]" won the [[Academy Award for Best Original Song]].<ref>{{cite magazine|magazine=Billboard|title=The Billboard Eleventh Annual Disk Jockey Poll|url=https://books.google.com/books?id=7AoEAAAAMBAJ&pg=PA36|date=December 15, 1958|page=36|issn=0006-2510|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429145219/https://books.google.com/books?id=7AoEAAAAMBAJ&pg=PA36|url-status=live}}</ref> By 1958, Sinatra was one of the ten biggest box office draws in the United States,{{sfn|Kelley|1986|p=282}} appearing with Dean Martin and [[Shirley MacLaine]] in [[Vincente Minnelli]]'s ''[[Some Came Running (film)|Some Came Running]]'' and ''[[Kings Go Forth]]'' (both 1958) with [[Tony Curtis]] and [[Natalie Wood]].{{sfnm|1a1=Early|1y=2004|1p=16|2a1=O'Brien|2y=2014|2pp=236, 243}} "[[High Hopes (1959 song)|High Hopes]]", sung by Sinatra in the [[Frank Capra]] comedy, ''[[A Hole in the Head]]'' (1959),<ref>{{cite book|title=Italian Americana&nbsp;– A Hole in the Head|url=https://books.google.com/books?id=dS92AAAAMAAJ|year=1976|publisher=State University of New York College at Buffalo.|page=251|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429111448/https://books.google.com/books?id=dS92AAAAMAAJ|url-status=live}}</ref>{{sfn|Marill|1990|p=184}} won the Academy Award for Best Original Song,<ref>{{cite web | url=https://www.oscars.org/oscars/ceremonies/1960 | title=The 32nd Academy Awards | date=October 5, 2014 | publisher=[[Academy Awards|Academy of Motion Picture Arts and Sciences]] | access-date=October 1, 2015 | archive-date=December 15, 2019 | archive-url=https://web.archive.org/web/20191215135341/https://oscars.org/oscars/ceremonies/1960 | url-status=live }}</ref> and became a chart hit, lasting on the [[Billboard Hot 100|Hot 100]] for 17 weeks.{{sfn|Sackett|1995|p=152}}

=== 1960–1980: Later career ===
[[File:SinatraGraumans.jpg|left|thumb|Sinatra leaving his signature in concrete at Grauman's Chinese Theatre in Hollywood, California on July 21, 1965]]
Due to an obligation, he owed to [[20th Century Fox]] for walking off the set of [[Henry King (director)|Henry King]]'s ''[[Carousel (film)|Carousel]]'' (1956),{{efn|Sinatra had stormed off the set when he learned that the film was to be shot in both Cinemascope and a new 55-millimeter process. Refusing to make "two pictures for the price of one", he left the production and did not return. Fox initially sued Sinatra for a million dollars for breach of contract and replaced him with [[Gordon MacRae]]. Fox agreed to drop the claim on condition that he appear in another picture of theirs.{{sfn|Hickey|2015|p=76}}}} Sinatra starred opposite [[Shirley MacLaine]], [[Maurice Chevalier]] and [[Louis Jourdan]] in ''[[Can-Can (film)|Can-Can]]'' (1960). He earned $200,000 and 25% of the profits for the performance.{{sfn|Santopietro|2008|p=273}} Around the same time, he starred in the Las Vegas-set ''[[Ocean's 11]]'' (1960), the first film to feature the Rat Pack together and the start of a "new era of screen cool" for Santopietro.{{sfn|Santopietro|2008|p=285}} Sinatra personally financed the film and paid Martin and Davis fees of $150,000 and $125,000, respectively, sums considered exorbitant for the period.{{sfn|Rojek|2004|p=144}} He had a leading role opposite [[Laurence Harvey]] in ''[[The Manchurian Candidate (1962 film)|The Manchurian Candidate]]'' (1962), which he considered to be the role he was most excited about and the high point of his film career.{{sfnm|1a1=Sinatra|1y=1986|1p=336|2a1=Santopietro|2y=2008|2p=295}} [[Vincent Canby]], writing for the magazine ''Variety'', found the portrayal of Sinatra's character to be "a wide-awake pro creating a straight, quietly humorous character of some sensitivity."<ref>{{cite web | url=https://variety.com/1962/film/reviews/the-manchurian-candidate-1200420234/ | title=Review: 'The Manchurian Candidate' | work=Variety | date=October 17, 1962 | access-date=October 30, 2015 | author=Canby, Vincent | archive-date=October 10, 2015 | archive-url=https://web.archive.org/web/20151010102556/http://variety.com/1962/film/reviews/the-manchurian-candidate-1200420234/ | url-status=live }}</ref> He appeared with the Rat Pack in the western ''[[Sergeants 3]]'' (1962),{{sfn|Rojek|2004|p=144}} and again in the 1964 gangster-oriented musical ''[[Robin and the 7 Hoods]]''. For his performance in ''[[Come Blow Your Horn (film)|Come Blow Your Horn]]'' (1963), adapted from the [[Neil Simon]] play, he was nominated for the [[Golden Globe Award]] for Best Actor{{nbsp}}– Motion Picture Musical or Comedy.<ref name=GoldenGlobes />

[[File:Frank Sinatra as Tony Rome (alt).jpg|thumb|upright|Sinatra in ''[[Tony Rome]]'' (1967)]]
Sinatra directed ''[[None but the Brave]]'' (1965),{{sfn|Knight|2010|p=262}} and ''[[Von Ryan's Express]]'' <!-- released five months later in the US. -->(1965) was a major success.<ref>{{cite web|url=https://www.tcm.com/tcmdb/title/24787/marriage-on-the-rocks#articles-reviews|title=Marriage on the Rocks (1965)|publisher=Turner Classic Movies|access-date=October 3, 2015|author=LoBianco, Lorraine|archive-date=October 4, 2015|archive-url=https://web.archive.org/web/20151004131156/http://www.tcm.com/tcmdb/title/24787/Marriage-on-the-Rocks/articles.html|url-status=live}}</ref><ref>{{cite web|url=https://timeout.com/london/film/von-ryans-express-1965|title=Von Ryan's Express|work=Time Out|date=September 10, 2012 |access-date=October 3, 2015|archive-date=October 1, 2015|archive-url=https://web.archive.org/web/20151001233852/http://www.timeout.com/london/film/von-ryans-express-1965|url-status=live}}</ref> In the late 1960s, Sinatra became known for playing detectives,{{Sfn|Santopietro|2008|p=388}} including Tony Rome in ''[[Tony Rome]]'' (1967) and its sequel ''[[Lady in Cement]]'' (1968).<ref>{{cite web|url=https://rogerebert.com/reviews/tony-rome-1967|title=Tony Rome|publisher=RogerEbert.com|date=November 22, 1967|access-date=October 4, 2015|author=Ebert, Roger|archive-date=October 5, 2015|archive-url=https://web.archive.org/web/20151005012713/http://www.rogerebert.com/reviews/tony-rome-1967|url-status=live}}</ref><ref>{{cite news|url=https://www.nytimes.com/movie/review?res=9F01E4DA1230EF34BC4951DFB7678383679EDE|title=Lady in Cement' Here|work=The New York Times|date=November 21, 1968|access-date=October 4, 2015|last=Canby|first=Vincent|archive-date=March 7, 2016|archive-url=https://web.archive.org/web/20160307102655/http://www.nytimes.com/movie/review?res=9F01E4DA1230EF34BC4951DFB7678383679EDE|url-status=live}}</ref> He played a similar role in ''[[The Detective (1968 film)|The Detective]]'' (1968).<ref>{{cite web|url=https://rogerebert.com/reviews/the-detective-1968|title=The Detective|publisher=RogerEbert.com|date=July 12, 1968|access-date=October 4, 2015|author=Ebert, Roger|archive-date=October 5, 2015|archive-url=https://web.archive.org/web/20151005115519/http://www.rogerebert.com/reviews/the-detective-1968|url-status=live}}</ref> As ''[[Die Hard]]'' was based on the novel sequel to ''The Detective'', the studio{{vague|date=January 2025}}{{specify|date=January 2025}} was contractually obliged to offer Sinatra the role. Sinatra, who was 70 at the time, declined.<ref name="GeekDieHard">{{cite web | last=George | first=Joe | title=Frank Sinatra Starred in the Die Hard Prequel You Probably Never Saw | website=Den of Geek | date=2023-07-04 | url=https://www.denofgeek.com/movies/frank-sinatra-starred-in-the-die-hard-prequel-you-probably-never-saw/ | access-date=2025-03-13}}</ref><ref name="DieHardNR">{{cite web | title=Turns Out Frank Sinatra Was Offered the Role of John McClane in Die Hard | website=National Review | date=2021-11-23 | url=https://www.nationalreview.com/corner/turns-out-frank-sinatra-was-offered-the-role-of-john-mcclane-in-die-hard/ | access-date=2025-03-13}}</ref>

Sinatra starred opposite [[George Kennedy]] in the western ''[[Dirty Dingus Magee]]'' (1970), an "abysmal" affair according to Santopietro,{{sfn|Santopietro|2008|p=409}} which was panned by the critics.{{sfn|Santopietro|2008|p=414}}<ref>{{cite web|author=Ebert, Roger|url=https://rogerebert.com/reviews/dirty-dingus-magee-1970|title=Dirty Dingus Magee|publisher=RogerEbert.com|date=November 23, 1970|access-date=August 31, 2015|archive-date=September 24, 2015|archive-url=https://web.archive.org/web/20150924125527/http://www.rogerebert.com/reviews/dirty-dingus-magee-1970|url-status=live}}</ref> The following year, Sinatra received a [[Golden Globe Cecil B. DeMille Award]]<ref name=GoldenGlobes /> and had intended to play Detective [[Harry Callahan (character)|Harry Callahan]] in ''[[Dirty Harry]]'' (1971), but had to turn down the role due to developing [[Dupuytren's contracture]] in his hand.{{sfn|Santopietro|2008|pp=414–415}} Sinatra's last major film role was opposite [[Faye Dunaway]] in [[Brian G. Hutton]]'s ''[[The First Deadly Sin]]'' (1980). Santopietro said that as a troubled New York City homicide cop, Sinatra gave an "extraordinarily rich", heavily layered characterization, one which "made for one terrific farewell" to his film career.{{sfn|Santopietro|2008|p=648}}

== Television and radio career ==
[[File:Frank Sinatra (1944 CBS Radio publicity photo).jpg|thumb|upright|Sinatra on CBS Radio in 1944]]
After beginning on the ''[[Major Bowes Amateur Hour]]'' radio show with the Hoboken Four in 1935, and later WNEW and WAAT in Jersey City,{{sfn|Santopietro|2008|p=27}} Sinatra became the star of radio shows of his own on [[NBC]] and [[CBS]] from the early 1940s to the mid-1950s. In 1942, Sinatra hired arranger Axel Stordahl away from Tommy Dorsey before he began his first radio program that year, keeping Stordahl with him for all of his radio work..<ref name="dunningota">{{cite book |url=https://books.google.com/books?id=EwtRbXNca0oC&dq=%22Frank+Sinatra+Show+musical%22+%22For+his+own+radio+shows,+Sinatra+hired+arranger+Axel+Stordahl+away+from+Dorsey%22&pg=PA260 |author=Dunning, John |author-link=John Dunning (detective fiction author) |title=On the Air: The Encyclopedia of Old-Time Radio |section=Frank Sinatra Show |date=1998 |publisher=Oxford University Press |location=New York, NY |isbn=978-0-19-507678-3 |pages=260–261 |edition=Revised |access-date=2025-02-28}}</ref>  By the end of 1942, he was named the "Most Popular Male Vocalist on Radio" in a ''DownBeat'' poll.<ref>{{cite news|url=https://www.newspapers.com/clip/3406256/sinatra_most_popular_vocalist_on_radio/|title=Sinatra Most Popular Vocalist on Radio|work=Harrisburg Telegraph ([[Harrisburg, Pennsylvania]])|date=January 16, 1943|page=45|access-date=October 12, 2015|via=[[Newspapers.com]]|archive-date=March 6, 2016|archive-url=https://web.archive.org/web/20160306095307/https://www.newspapers.com/clip/3406256/sinatra_most_popular_vocalist_on_radio/|url-status=live}} {{Open access}}</ref> Early on he frequently worked with [[The Andrews Sisters]] on radio. They would appear as guests on each other's shows,{{sfn|Nimmo|2004|p=228}} as well as on many USO shows broadcast to troops via the [[Armed Forces Radio Service]] (AFRS).{{sfn|Sforza|2015|p=80}} He appeared as a special guest in the sisters' ABC ''Eight-to-the-Bar Ranch'' series,{{sfn|Nimmo|2004|p=444}} while the trio in turn guested on his ''[[Songs by Sinatra]]'' series on CBS.{{sfn|Sforza|2015|p=99}} Sinatra had two stints as a regular member of the cast of ''[[Your Hit Parade]]'';{{efn| ''[[Your Hit Parade]]'' was a popular weekly radio and television program from 1935 to 1958. Sponsored by American Tobacco Company's Lucky Strike brand of cigarettes, the show featured the top ten songs of each week.{{sfn|Nachman|2000|pp=170–173}}}} his first was from 1943 to 1945,{{sfn|Kaplan|2011|p=196}} and second was from 1946 to May 28, 1949,{{sfn|Dunning|1998|p=738}} during which he was paired with the then-new girl singer, [[Doris Day]].{{sfn|Nachman|2000|p=172}} Starting in September 1949, the [[BBDO|BBD&O]] advertising agency produced a radio series starring Sinatra for Lucky Strike called ''Light Up Time''{{nbsp}}– some 176 15-minute shows that featured him and [[Dorothy Kirsten]] singing{{nbsp}}– which lasted through to May 1950.{{sfnm|1a1=Ridgeway|1y=1977|1p=59|2a1=Sinatra|2y=1986|2p=70}}

In October 1951, the second season of ''[[The Frank Sinatra Show (CBS TV series)|The Frank Sinatra Show]]'' began on [[CBS Television]]. Ultimately, Sinatra did not find the success on television for which he had hoped.{{efn|Producer [[Irving Mansfield]] described Sinatra as being obsessed with the thought that his wife, Ava Gardner, was having an affair with her former husband, Artie Shaw. He often started shouting about this on the set of the television show when he phoned his home and could not reach Gardner. Mansfield had to communicate with Sinatra through the entourage that always accompanied him to CBS. Sinatra was always late to work and did not care to spend any time at rehearsal; he blamed all those connected with the program for the poor ratings it received. Mansfield was at his wits' end with Sinatra and his television show and quit the program. Mansfield informed him that he was a man of great talent but a failure as a person, which led to Sinatra attempting to angrily fire him. Mansfield replied that he was too late, as he had resigned that morning.{{sfn|Hernandez|2010|pp=284–285}}}} Santopietro writes that Sinatra "never appeared fully at ease on his own television series."{{sfn|Santopietro|2008|p=113}} In 1953 and 1954, Sinatra starred in the NBC radio program ''[[Rocky Fortune]]'', portraying Rocco Fortunato (a.k.a. Rocky Fortune).{{Sfn|Terrace|1998|p=287}}

[[File:Dean Martin Show 1958 Dean Martin Frank Sinatra.JPG|thumb|left|upright|Dean Martin with Sinatra on ''[[The Dean Martin Show]]'' in 1958]]
In 1957, Sinatra formed a three-year $3{{nbsp}}million contract with ABC to launch ''[[The Frank Sinatra Show (ABC)|The Frank Sinatra Show]]'', featuring himself and guests in 36 half-hour shows. ABC agreed to allow Sinatra's Hobart Productions to keep 60% of the residuals and bought stock in Sinatra's film production unit, Kent Productions, guaranteeing him $7{{nbsp}}million.{{Sfn|Kelley|1986|p=278}} Though an initial critical success upon its debut on October 18, 1957, it soon attracted negative reviews from ''Variety'' and ''[[The New Republic]]'', and ''[[The Chicago Sun-Times]]'' thought that Sinatra and frequent guest Dean Martin "performed like a pair of adult delinquents", "sharing the same cigarette and leering at girls."{{Sfn|Kelley|1986|p=280}} In return, Sinatra later made numerous appearances on ''[[The Dean Martin Show]]'' and Martin's TV specials.{{Sfn|Terrace|2013|p=123}}

Sinatra's fourth and final [[Timex Group USA|Timex]] TV special, ''[[The Frank Sinatra Timex Show: Welcome Home Elvis|Welcome Home Elvis]]'', was broadcast in March 1960, earning massive viewing figures. During the show, he performed a duet with Presley, who sang Sinatra's 1957 hit "[[Witchcraft (1957 song)|Witchcraft]]" with the host performing the 1956 Presley classic "[[Love Me Tender (song)|Love Me Tender]]". Sinatra had previously been highly critical of [[Elvis Presley]] and rock and roll in the 1950s, describing it as a "deplorable, a rancid smelling aphrodisiac" that "fosters almost totally negative and destructive reactions in young people."{{sfn|Kelley|1986|p=283}}{{efn|Presley had responded to the criticism: "...{{nbsp}}[Sinatra] is a great success and a fine actor, but I think he shouldn't have said it{{nbsp}}... [rock and roll] is a trend, just the same as he faced when he started years ago."{{sfn|Hopkins|2011|p=126}}}} A [[CBS News]] special about Sinatra's 50th birthday, ''[[Frank Sinatra: A Man and His Music]]'', was broadcast on November 16, 1965, and received an Emmy award and a [[Peabody Award]].{{sfn|Sinatra|1986|p=306}}

Continuing his musical collaboration with Jobim and [[Ella Fitzgerald]] in 1967, Sinatra appeared in the TV special, ''[[A Man and His Music + Ella + Jobim]]'', which was broadcast on CBS on November 13.{{sfn|Terrace|2013|p=157}} When Sinatra came out of retirement in 1973, he appeared in a TV special that shared its title with his contemporaneously released album, ''Ol' Blue Eyes Is Back''.{{sfn|Turner|2004|p=167}} In the late 1970s, [[John Denver]] appeared as a guest in the ''Sinatra and Friends'' ABC-TV Special, singing "September Song" as a duet.{{Sfn|Rees|Crampton|1999|p=286}}

Sinatra starred as a detective in ''[[Contract on Cherry Street]]'' (1977), cited as his "one starring role in a dramatic television film".{{sfn|Santopietro|2008|p=430}} Ten years later, he made a guest appearance opposite [[Tom Selleck]] in ''[[Magnum, P.I.]]''. Shot in January 1987, the episode aired on CBS on February 25.{{sfn|O'Brien|1998}}

== Personal life ==
{{Main|Personal life of Frank Sinatra}}
[[File:Sinatra family 1949.jpg|thumb|alt=Photo family portrait of a husband, wife, two young children, and an infant.|Family portrait, 1949. Sinatra with (from left) [[Nancy Sinatra|Nancy]], [[Tina Sinatra|Tina]], Nancy Barbato and [[Frank Sinatra Jr.|Frank Jr.]]]]
Sinatra was married to Nancy Sinatra (née Barbato) from 1939 to 1951. The couple had three children, [[Nancy Sinatra|Nancy]] (born 1940), [[Frank Sinatra Jr.|Frank Jr.]] (1944–2016), and [[Tina Sinatra|Tina]] (born 1948).<ref>{{cite news|url=http://news.bbc.co.uk/2/hi/special_report/1998/05/98/sinatra/94184.stm|title=Frank Sinatra's love and marriage|work=BBC News|date=May 15, 1998|access-date=October 9, 2015|archive-date=December 8, 2015|archive-url=https://web.archive.org/web/20151208215831/http://news.bbc.co.uk/2/hi/special_report/1998/05/98/sinatra/94184.stm|url-status=live}}</ref><ref>{{cite news |last1=Fox |first1=Margalit |title=Nancy Barbato Sinatra, an Idol's First Wife and Lasting Confidante, Dies at 101 |url=https://www.nytimes.com/2018/07/14/obituaries/nancy-barbato-sinatra-dead.html |access-date=July 14, 2018 |work=[[The New York Times]] |date=July 14, 2018 |language=en |archive-url=https://web.archive.org/web/20180714053447/https://www.nytimes.com/2018/07/14/obituaries/nancy-barbato-sinatra-dead.html |archive-date=July 14, 2018 |url-status=live}}</ref>

Sinatra met Barbato in [[Long Branch, New Jersey]], in the summer of 1934{{sfn|Santopietro|2008|p=37}} while working as a [[lifeguard]].{{sfn|Hazard|2007|p=99}} He agreed to marry her after an incident at "The Rustic Cabin" that led to his arrest.{{efn|While working at "The Rustic Cabin" in 1939, he became involved in a dispute between his girlfriend, Toni Della Penta, who suffered a miscarriage, and Nancy Barbato, a stonemason's daughter. After Della Penta attempted to tear off Barbato's dress, Sinatra ordered Barbato away and told Della Pinta that he would marry Barbato, several years his junior, because she was pregnant. Della Penta went to the police, and Sinatra was arrested on a morals charge for seduction. After a fight between Della Penta and Dolly, Della Penta was later arrested herself.{{sfn|Wilson|Wilson|2011}} Sinatra married Barbato that year,{{sfn|Turner|2004|p=15}} and Nancy Sinatra was born the following year.{{sfn|Goldstein|1982|p=8}}}} Sinatra had numerous extramarital affairs,{{sfn|Kelley|1986|pp=62–64}} and gossip magazines published details of affairs with women including [[Marilyn Maxwell]], [[Lana Turner]] and [[Joi Lansing]].{{sfn|Kelley|1986|p=127}}<ref>{{Cite web |date=June 3, 2021 |title=Frank Sinatra was told that Marilyn Monroe was murdered, new book claims |url=https://www.independent.co.uk/arts-entertainment/books/frank-sinatra-marilyn-monroe-b1859014.html |access-date=October 23, 2023 |website=The Independent |language=en}}</ref>{{efn|Turner later said the statements were not true in her 1992 autobiography, saying, "The closest things to dates Frank and I enjoyed were a few box lunches at MGM."{{Sfn|Summers|Swan|2010|p=157}}}}

{{quote box|width=22em|bgcolor=#c6dbf7|align=left|quote="Frank attracted women. He couldn't help it. Just to look at him—the way he moved, and how he behaved—was to know that he was a great lover and true gentleman. He adored the company of women and knew how to treat them. I had friends whose husbands were 'players', and every time the husbands had affairs my friends were showered with gifts. Well, I was constantly showered with gifts, but no matter what temptations Frank may have had while I wasn't around, he made me feel so safe and loved that I never became paranoid about losing him."|source=—Barbara Sinatra on Sinatra's popularity with women.{{sfn|Sinatra|2011|p=219}}}}

Sinatra was married to Hollywood actress [[Ava Gardner]] from 1951 to 1957. It was a turbulent marriage with many well-publicized fights and altercations.{{Sfn|Kelley|1986|p=202}} The couple formally announced their separation on October 29, 1953, through MGM.{{sfn|Kelley|1986|p=229}} Gardner filed for divorce in June 1954, at a time when she was dating matador [[Luis Miguel Dominguín]],{{sfn|Wayne|2004|p=15}} but the divorce was not settled until 1957.{{sfn|Sonneborn|2002|p=79}} Sinatra continued to feel very strongly for her,{{sfn|Sonneborn|2002|p=79}} and they remained friends for life.{{Sfn|Santopietro|2008|p=221}}

In 1957, Sinatra moved to a home in [[Rancho Mirage, California]], called The Compound.<ref name="Baker2008">{{cite book |author=Christopher P. Baker |url=https://books.google.com/books?id=dtUqQKw2H9EC |title=Explorer's Guide Palm Springs & Desert Resorts: A Great Destination (Explorer's Great Destinations) |date=3 November 2008 |publisher=The Countryman Press |isbn=978-1-58157-971-0 |page=117}}</ref>

Sinatra reportedly broke off engagements to [[Lauren Bacall]] in 1958{{sfn|Lahr|2000|pp=76–77}} and [[Juliet Prowse]] in 1962.{{sfn|Rojek|2004|pp=107–108}} He was romantically linked to [[Marilyn Monroe]], [[Pat Sheehan (model)|Pat Sheehan]], [[Vikki Dougan]], and [[Kipp Hamilton]].<ref>Clemens, Samuel. "Hollywood's Irish Lass", ''[[Classic Images]]''. p.13. July 2022</ref> Sinatra and [[Mia Farrow]] were married on July 19, 1966, and the couple divorced in August 1968.{{Sfn|Santopietro|2008|pp=361, 398}} They remained close friends for life,{{Sfn|Santopietro|2008|p=361}} and in a 2013 interview, Farrow said that Sinatra might be the father of her son, [[Ronan Farrow]] (born 1987).<ref name="GuardianFarrow">{{cite web | url=https://www.theguardian.com/film/2013/oct/02/woody-allen-son-ronan-frank-sinatra-mia-farrow | title=Mia Farrow: Woody Allen's son Ronan may be Frank Sinatra's | work=The Guardian | date=October 2, 2013 | access-date=October 7, 2015 | author=Shoard, Catherine | archive-date=October 7, 2013 | archive-url=https://web.archive.org/web/20131007123549/http://www.theguardian.com/film/2013/oct/02/woody-allen-son-ronan-frank-sinatra-mia-farrow | url-status=live }}</ref><ref>{{cite news| url = http://www.vanityfair.com/online/daily/2013/10/mia-farrow-children-family-scandal | title = Mia Farrow and Eight of Her Children Speak Out on Their Lives, Frank Sinatra, and the Scandals They've Endured| work = [[Vanity Fair (magazine)|Vanity Fair]] | date=October 2, 2013 | access-date=October 2, 2013 | archive-url=https://web.archive.org/web/20131031041558/http://www.vanityfair.com/online/daily/2013/10/mia-farrow-children-family-scandal | archive-date=October 31, 2013}}</ref> In a 2015 ''CBS Sunday Morning'' interview, Nancy Sinatra dismissed the claim as "nonsense". She said that her father had a [[vasectomy]] years before Farrow's birth.<ref>{{Cite news|last=Heller|first=Corinne|url=http://www.eonline.com/news/642284/nancy-sinatra-opens-up-about-frank-sinatra-sister-mia-farrow-and-ronan-farrow-paternity-rumor|title=Nancy Sinatra Opens Up About Frank Sinatra, Mia Farrow & Son Ronan|work=E! Online|access-date=November 6, 2017|language=en-US|archive-date=November 7, 2017|archive-url=https://web.archive.org/web/20171107032011/http://www.eonline.com/news/642284/nancy-sinatra-opens-up-about-frank-sinatra-sister-mia-farrow-and-ronan-farrow-paternity-rumor|url-status=live}}</ref><ref>[https://www.billboard.com/articles/news/6523895/ronan-farrow-frank-sinatra-son-nancy-sinatra Ronan Farrow Is Frank Sinatra's Son? Nancy Sinatra Says That's 'Nonsense']. ''Billboard''. April 2, 2015.</ref>

Sinatra was married to [[Barbara Marx]] from 1976 until his death.<ref>{{cite news | url=https://www.telegraph.co.uk/news/features/8556824/My-life-with-Frank-Sinatra.html | title=My life with Frank Sinatra | work=The Daily Telegraph | agency=June 5, 2011 | access-date=October 7, 2015 | author=Elsworth, Catherine | archive-date=January 21, 2019 | archive-url=https://web.archive.org/web/20190121040603/https://www.telegraph.co.uk/news/features/8556824/My-life-with-Frank-Sinatra.html | url-status=live }}</ref> The couple married on July 11, 1976, at [[Sunnylands]], in [[Rancho Mirage, California]], the estate of media magnate [[Walter Annenberg]].{{sfn|Sinatra|1986|pp=249–250}}

Sinatra was close friends with [[Jilly Rizzo]],{{sfn|Sinatra|2011|p=94}} songwriter Jimmy Van Heusen, golfer [[Ken Venturi]], comedian [[Pat Henry (comedian)|Pat Henry]], baseball manager [[Leo Durocher]], and president [[John F. Kennedy]] (for whom he organized an [[United States presidential inaugural balls|inaugural ball]] with [[Peter Lawford]]).{{sfn|Sinatra|2011|p=3}} In his spare time, he enjoyed listening to classical music.{{sfn|Friedwald|1995|p=21}} He swam daily in the Pacific Ocean.{{sfn|Granata|2003|p=95}} He often played golf with Venturi at the course in Palm Springs, where he lived in the house [[Twin Palms]] he had commissioned from [[E. Stewart Williams]] in 1947{{sfn|Sinatra|1986|p=242}}<ref>{{cite web |title=History |url=https://sinatrahouse.com/about-twin-palms/ |website=The Sinatra House |date=May 2, 2011 |access-date=December 27, 2023}}</ref> He liked painting, reading, and building model railways.{{sfn|Sinatra|2011|p=128}}

Though Sinatra was critical of the church on numerous occasions{{Sfn|Kelley|1986|p=493}} and had a [[Albert Einstein's religious views|pantheistic, Einstein-like view of God]] in his earlier life,<ref name=religion>{{cite news|url=http://sinatrafamily.com/forum/29275-Frank-Sinatra-s-1963-Playboy-Magazine-Interview.htm|title=Frank Sinatra's February 1963 Playboy Magazine Interview|last=Hyams|first=Joe|date=February 1963|work=Playboy|access-date=August 19, 2014|archive-date=October 9, 2014|archive-url=https://web.archive.org/web/20141009140229/http://sinatrafamily.com/forum/29275-Frank-Sinatra-s-1963-Playboy-Magazine-Interview.htm|url-status=live}}</ref> he was inducted into the Catholic [[Sovereign Military Order of Malta]] in 1976,<ref>{{Cite news|title=Saturday Review|url=https://www.newspapers.com/article/the-sydney-morning-herald-frank-sinatra/79447815/|access-date=June 13, 2021|newspaper=The Sydney Morning Herald| date=August 3, 1985 | page=41 |language=en}}</ref> and he turned to [[Catholic Church|Catholicism]] for healing after his mother died in a plane crash in 1977. He died as a practicing Catholic and had a Catholic burial.<ref>{{cite web|url=http://www.people.com/people/archive/article/0,,20125409,00.html|title=A Swinger with Swagger|work=People|date=June 1, 1998|first1=Alex|last1=Tresniowski|first2=Richard|last2=Lacayo|access-date=August 17, 2015|archive-date=September 24, 2015|archive-url=https://web.archive.org/web/20150924150106/http://www.people.com/people/archive/article/0,,20125409,00.html|url-status=live}}</ref>

=== Style and personality ===
Sinatra was known for his immaculate sense of style.{{sfn|Sinatra|2011|p=131}} He spent lavishly on expensive custom-tailored tuxedos and stylish pin-striped suits, which made him feel wealthy and important and that he was giving his very best to the audience.{{sfn|Santopietro|2008|p=51}}{{sfn|Kelley|1986|p=51}} He was also obsessed with cleanliness—while with the Tommy Dorsey band, he developed the nickname "Lady Macbeth" because of frequent showering and switching his outfits.{{sfn|Levinson|2001|p=116}} His deep blue eyes earned him the popular nickname "Ol' Blue Eyes".{{sfn|Sirvaitis|2010|p=23}}

[[File:Frank Sinatra in 1955.jpg|thumb|upright|left|Sinatra in 1955]]
For Santopietro, Sinatra was the personification of America in the 1950s: "cocky, eye on the main chance, optimistic, and full of the sense of possibility."{{sfn|Santopietro|2008|p=231}} Barbara Sinatra wrote, "A big part of Frank's thrill was the sense of danger that he exuded, an underlying, ever-present tension only those closest to him knew could be defused with humor."{{sfn|Sinatra|2011|p=3}} [[Cary Grant]], a friend of Sinatra, stated that Sinatra was the "most honest person he'd ever met", who spoke "a simple truth, without artifice which scared people", and was often moved to tears by his performances.{{sfn|Sinatra|2011|p=224}} Jo-Caroll Dennison commented that he possessed "great inner strength" and that his energy and drive were "enormous."{{sfn|Summers|Swan|2010|p=151}} A workaholic, he reportedly only slept four hours a night on average.{{sfn|Santopietro|2008|p=16}} Throughout his life, Sinatra had mood swings and bouts of mild to severe [[Depression (mood)|depression]],{{sfn|Sinatra|Coplon|2000|p=47}} stating to an interviewer in the 1950s that "I have an over-acute capacity for sadness as well as elation."{{sfn|Summers|Swan|2010|p=218}} Barbara Sinatra stated that he would "snap at anyone for the slightest misdemeanor",{{sfn|Sinatra|2011|p=148}} while Van Heusen said that when Sinatra got drunk, it was "best to disappear."{{sfn|Sinatra|2011|p=155}}

Sinatra's mood swings often developed into violence, directed at people he felt had crossed him, particularly journalists who gave him scathing reviews, publicists, and photographers.{{sfn|Kelley|1986|pp=249–250}} According to Rojek, he was "capable of deeply offensive behavior that smacked of a persecution complex."{{sfn|Rojek|2004|p=141}} He received negative press for fights with [[Lee Mortimer]] in 1947, photographer Eddie Schisser in [[Houston]] in 1950, Judy Garland's publicist [[Jim Byron]] on the [[Sunset Strip]] in 1954,{{sfn|Kelley|1986|pp=249–250}}<ref>{{cite news|url=https://www.newspapers.com/clip/3405214/sinatra_vs_jim_byron/|title=Sinatra, Press Agent Trade Blows, Few of Which Connect|work=Oneonta Star ([[Oneonta, New York]])|date=December 10, 1954|page=1|access-date=October 12, 2015|via=[[Newspapers.com]]|archive-date=December 22, 2015|archive-url=https://web.archive.org/web/20151222102043/https://www.newspapers.com/clip/3405214/sinatra_vs_jim_byron/|url-status=live}} {{Open access}}</ref> and for a confrontation with ''[[Washington Post]]'' journalist [[Maxine Cheshire]] in 1973, in which he implied that she was a cheap prostitute.{{sfn|Rojek|2004|p=141}}{{efn|Rojek states that Sinatra verbally assaulted Cheshire at a party in 1973, remarking, "Get away from me, you scum. Go home and take a bath{{nbsp}}... You're nothing but a two-dollar cunt. You know what that means, don't you? You've been laying down for two dollars all your life". According to Rojek, Sinatra then proceeded to place two-dollar bills in her wine glass and remarked, "Here's two dollars, baby, that's what you're used to."{{sfn|Rojek|2004|p=141}}}} His feud with then-''[[Chicago Sun Times]]'' columnist [[Mike Royko]] began when Royko wrote a column questioning why Chicago police offered free protection to Sinatra when he had his own security. Sinatra wrote an angry letter in response, calling Royko a "pimp" and threatening to "punch you in the mouth" for speculating that he wore a [[toupée]].<ref>[https://lettersofnote.com/2009/11/30/youre-nothing-but-a-pimp/ You're Nothing but a Pimp] {{Webarchive|url=https://web.archive.org/web/20200603045758/https://lettersofnote.com/2009/11/30/youre-nothing-but-a-pimp/ |date=June 3, 2020 }} ''lettersofnote.com'' (November 30, 2009); retrieved April 18, 2020</ref>

Sinatra was also known for his generosity,{{sfn|Sinatra|2011|p=146}} particularly after his comeback. Kelley notes that when [[Lee J. Cobb]] nearly died from a heart attack in June 1955, Sinatra flooded him with "books, flowers, delicacies", paid his hospital bills, and visited him daily, telling him that his "finest acting" was yet to come.{{sfn|Kelley|1986|pp=251–252}}

=== Alleged organized-crime links and Cal Neva Lodge ===
[[File:LuckyLucianoSmaller.jpeg|thumb|upright|Mobster [[Lucky Luciano]]]]
Sinatra became the stereotype of the "tough working-class Italian American", something which he embraced. He said that if it had not been for his interest in music, he would have likely ended up in a life of crime.{{sfn|McNally|2015|p=50}} [[Willie Moretti]] was Sinatra's godfather and the notorious [[underboss]] of the [[Genovese crime family]], and he helped Sinatra in exchange for kickbacks and was reported to have intervened in releasing Sinatra from his contract with Tommy Dorsey.{{sfn|Sifakis|2005|p=420}} Sinatra was present at the Mafia [[Havana Conference]] in 1946,{{sfn|Sifakis|2005|p=419}} and the press learned of his being there with [[Lucky Luciano]]. One newspaper published the headline "Shame, Sinatra".{{sfn|Lahr|2000|p=63}} He was reported to be a good friend of mobster [[Sam Giancana]],{{sfn|Santopietro|2008|p=343}} Kelley quoted Jo-Carrol Silvers that Sinatra "adored" [[Bugsy Siegel]] and boasted to friends about him and how many people Siegel had killed.{{sfn|Kelley|1986|pp=124–125}} Kelley says that Sinatra and mobster [[Joseph Fischetti]] had been good friends from 1938 onward and acted like "Sicilian brothers".{{sfn|Kelley|1986|p=135}} She also states that Sinatra and [[Hank Sanicola]] were financial partners with [[Mickey Cohen]] in the gossip magazine ''Hollywood Night Life''.{{sfn|Kelley|1986|p=176}} (Johnny) Roselli's membership in the Friars Club in Beverly Hills was sponsored by celebrity singer and Friars Club abbot Frank Sinatra.<ref>{{cite book |last1=Bash |first1=Avi |last2=Niotta |first2=J. Michael |year=2021 |title=Logo: Images of America Los Angeles Underworld |publisher=Arcadia Publishing |location=South Carolina |isbn=978-1-4671-0638-2 |page=89 |quote=...But when newly sponsored friar Johnny Roselli grew wise, he insisted on a one-fifth partnership.  Roselli's membership was sponsored by celebrity singer and Friars Club abbot Frank Sinatra}}</ref>

The FBI kept records amounting to 2,403 pages on Sinatra, who was a natural target with his alleged Mafia ties, his ardent [[New Deal]] politics, and his friendship with [[John F. Kennedy]].<ref>{{cite news|url=https://www.npr.org/templates/story/story.php?storyId=1075739|title=Sinatra: The FBI Files|newspaper=NPR|access-date=June 14, 2008|archive-date=January 8, 2009|archive-url=https://web.archive.org/web/20090108171522/http://www.npr.org/templates/story/story.php?storyId=1075739|url-status=live}}</ref> The FBI kept him under surveillance for almost five decades beginning in the 1940s. The documents include accounts of Sinatra as the target of death threats and extortion schemes.<ref>{{cite news|url=https://www.washingtonpost.com/wp-srv/national/daily/march99/sinatra7.htm|title=AKA Frank Sinatra|newspaper=The Washington Post Magazine|access-date=June 14, 2008|date=March 6, 1999|archive-date=July 26, 2008|archive-url=https://web.archive.org/web/20080726152122/http://www.washingtonpost.com/wp-srv/national/daily/march99/sinatra7.htm|url-status=live}}</ref> The FBI documented that Sinatra was losing esteem with the Mafia as he grew closer to President Kennedy, whose younger brother Attorney General [[Robert F. Kennedy]] was leading a crackdown on organized crime.{{sfn|Kelley|1986|pp=327–329}} Sinatra said he was not involved: "Any report that I fraternized with goons or racketeers is a vicious lie."{{sfn|McNally|2015|p=49}}

In 1960, Sinatra bought a share in the [[Cal Neva Lodge & Casino]], a casino hotel on the south shore of [[Lake Tahoe]]. Sinatra built the Celebrity Room theater, which attracted his show business friends [[Red Skelton]], [[Marilyn Monroe]], [[Victor Borge]], [[Joe E. Lewis]], [[Lucille Ball]], [[Lena Horne]], [[Juliet Prowse]], the [[McGuire Sisters]], and others. By 1962, he reportedly held a 50-percent share in the hotel.{{Sfn|Kelley|1986|pp=347–348, 355}} Sinatra's gambling license was temporarily suspended by the [[Nevada Gaming Control Board]] in 1963 after Giancana was spotted on the premises.<ref>{{cite web|last=Griffith|first=Martin|url=http://usatoday30.usatoday.com/travel/destinations/2010-03-31-lake-tahoe-rat-pack-casino_N.htm|title=Frank Sinatra's Lake Tahoe casino shuts down |work=USA Today|date=March 31, 2010|access-date=July 26, 2015|archive-url=https://web.archive.org/web/20131204182309/http://usatoday30.usatoday.com/travel/destinations/2010-03-31-lake-tahoe-rat-pack-casino_N.htm|archive-date=December 4, 2013}}</ref>{{efn|According to Kelley, Giancana blamed Sinatra for the ordeal and was fuming at the abuse he had given to the commission's chairman Ed Olsen. The two men never spoke again.{{sfn|Kelley|1986|pp=363–364}}}} Due to ongoing pressure from the FBI and Nevada Gaming Commission on mobster control of casinos, Sinatra agreed to give up his share in Cal Neva and the Sands.{{sfn|Waldman|Donovan|1999|p=139}} That year, his son [[Frank Sinatra Jr.#Kidnapping|Frank Jr. was kidnapped]] but was eventually released unharmed.<ref>{{cite news|url=https://www.newspapers.com/article/nashua-telegraph-sixties-considered-deca/170638629/|title=Sixties Considered Decade of Stress in Movie World|work=Nashua Telegraph ([[Nashua, New Hampshire]])|date=December 18, 1969|page=28|access-date=October 12, 2015|via=Newspapers.com|archive-date=November 26, 2015|archive-url=https://web.archive.org/web/20151126064602/https://www.newspapers.com/image/74976357/?terms=Frank%2BSinatra|url-status=live}} {{Open access}}</ref> Sinatra's gambling license was restored in February 1981, following support from [[Ronald Reagan]].{{Sfn|Santopietro|2008|p=408}}

== Political views and activism ==
{{Main|Political life of Frank Sinatra}}
[[File:Eleanor Roosevelt and Frank Sinatra in Los Angeles, California - NARA - 196117 (retouched).jpg|thumb|left|Sinatra, pictured with [[Eleanor Roosevelt]] in 1947, was an ardent supporter of the [[Democratic Party (United States)|Democratic Party]] until the early 1970s.]]
Sinatra held varied political views throughout his life. His mother, Dolly, was a [[Democratic Party (United States)|Democratic Party]] ward leader.{{sfn|Summers|Swan|2010|p=16}} After meeting President [[Franklin D. Roosevelt]] in 1944, he subsequently heavily campaigned for the Democrats in the [[1944 United States presidential election|1944 presidential election]].{{sfnm|1a1=Smith|1y=2005|1p=40|2a1=Summers|2a2=Swan|2y=2010|2p=125}} According to Jo Carroll Silvers, in his younger years, Sinatra had "ardent liberal" sympathies and was "so concerned about poor people that he was always quoting [[Henry A. Wallace|Henry Wallace]]."{{sfn|Kelley|1986|pp=118, 123}} He was outspoken against racism, particularly toward black people and Italians, from a young age. In the early 1950s, he was among those who campaigned to combine the racially segregated musicians' unions in Los Angeles.<ref name="Bryant1999">{{Cite book|title=Central Avenue Sounds: Jazz in Los Angeles|last=Bryant|first=Clara|publisher=University of California Press|year=1999|isbn=0-520-22098-6|location=Berkeley, CA|pages=154–159}}</ref> In November 1945, Sinatra was invited by the mayor of [[Gary, Indiana]], to try to settle a strike by white students of Froebel High School against the "Pro-Negro" policies of the new principal.{{sfn|Ingham|2005|p=26}} His comments, while praised by liberal publications, led to accusations by some that he was a [[Communism|communist]], which he denied.{{sfn|Kelley|1986|p=122–123}} In the [[1948 United States presidential election|1948 presidential election]], Sinatra actively campaigned for President [[Harry S. Truman]].<ref name="ws;">{{cite web|first=Steve|last=Pond|url=http://www.sinatra.com/legacy/frank-sinatra-and-politics|work=Legacy|title=Frank Sinatra and Politics|publisher=Sinatra.com|date=July 4, 1991|access-date=July 4, 2011|archive-url=https://web.archive.org/web/20110515000915/http://www.sinatra.com/legacy/frank-sinatra-and-politics|archive-date=May 15, 2011}}</ref> In 1952 and 1956, he campaigned for [[Adlai Stevenson II|Adlai Stevenson]].<ref name="ws;" />

[[File:Frank Sinatra and Ronald Reagan.jpg|thumb|Sinatra is awarded the [[Presidential Medal of Freedom]] by President [[Ronald Reagan]] in 1985.]]
Of all the U.S. presidents he associated with during his career, he was closest to John F. Kennedy.<ref name=ws; /> Sinatra often invited Kennedy to Hollywood and Las Vegas, and the two would womanize and enjoy parties together.{{sfn|Kelley|1986|pp=298–300}} In January 1961, Sinatra and [[Peter Lawford]] organized the [[United States presidential inaugural balls|Inaugural Gala]] in Washington, D.C., held on the evening before President Kennedy was sworn into office.<ref name=ws; /> After taking office, Kennedy distanced himself from Sinatra due partly to Sinatra's ties with the Mafia.<ref name=irishcentralreports>{{cite news|url=https://www.irishcentral.com/culture/what-s-the-connection-between-john-f-kennedy-and-frank-sinatra|title=What's the connection between John F. Kennedy and Frank Sinatra|first=James|last=Wilson|publisher=Irish Central|date=August 16, 2017|access-date=September 3, 2020|archive-date=November 28, 2020|archive-url=https://web.archive.org/web/20201128112653/https://www.irishcentral.com/culture/what-s-the-connection-between-john-f-kennedy-and-frank-sinatra|url-status=live}}</ref> In 1962, Sinatra was snubbed by the President as, during his visit to his [[Palm Springs, California|Palm Springs]], Kennedy stayed with the Republican Bing Crosby instead of Sinatra, citing FBI concerns about the latter's alleged connections to organized crime.{{efn| Kennedy was strongly advised by [[Henry E. Petersen]], a senior official of the Justice Department, to avoid staying with Sinatra.{{sfn|Kelley|1986|p=334}} }} Sinatra had spared no expense upgrading the facilities at his home in anticipation of the President's visit, fitting it with a heliport, which he smashed with a sledgehammer after the rejection.{{sfn|Thomas|2013|p=169}}<ref>{{Cite news|url=https://www.telegraph.co.uk/music/artists/sinatra-snow-storms-smashed-up-helipad-story-behind-john-f-kennedys/|title=Sinatra, snow storms, and a smashed-up helipad: the story behind John F Kennedy's star-studded inauguration|first=Alice|last=Vincent|newspaper=The Telegraph|date=January 19, 2017|via=www.telegraph.co.uk|access-date=September 3, 2020|archive-date=July 28, 2020|archive-url=https://web.archive.org/web/20200728210413/https://www.telegraph.co.uk/music/artists/sinatra-snow-storms-smashed-up-helipad-story-behind-john-f-kennedys/|url-status=live}}</ref> Despite the snub, when he learned of Kennedy's assassination he reportedly sobbed in his bedroom for three days.<ref name=ws; />{{efn|When Sinatra learned that Kennedy's killer [[Lee Harvey Oswald]] had watched ''Suddenly'' just days before the assassination, he withdrew it from circulation, and it only became distributed again in the late 1980s.{{sfn|Santopietro|2008|pp=151–152}}}} Sinatra worked with [[Hubert H. Humphrey]] in 1968,<ref>{{Cite journal|title=Ol' Red, White, and Blue Eyes: Frank Sinatra and the American Presidency|last=Nelson|first=Michael|year=2000|journal=Popular Music and Society|volume=24|issue=4|pages=79–102|doi=10.1080/03007760008591786|s2cid=159717929}}</ref> and remained a supporter of the Democratic Party until the early 1970s. Although still a registered Democrat, Sinatra endorsed [[Republican Party (United States)|Republican]] Ronald Reagan for a second term as [[Governor of California]] in 1970.{{sfn|Sinatra|1986|pp=224–227}}<ref name="ws;" /> He officially changed allegiance in July 1972 when he supported [[Richard Nixon]] in the [[1972 United States presidential election|1972 presidential election]].<ref name=ws; />

In the [[1980 United States presidential election|1980 presidential election]], Sinatra donated $4{{nbsp}}million to Ronald Reagan's campaign.<ref>{{cite web|url=https://www.telegraph.co.uk/culture/music/3673018/Frank-Sinatra-how-the-myth-was-made.html|title=Frank Sinatra: how the myth was made|work=The Daily Telegraph|date=April 30, 2008|access-date=October 4, 2015|author=Smart, Alastair|archive-date=October 7, 2015|archive-url=https://web.archive.org/web/20151007174636/http://www.telegraph.co.uk/culture/music/3673018/Frank-Sinatra-how-the-myth-was-made.html|url-status=live}}</ref> Sinatra arranged Reagan's Presidential gala, as he had done for Kennedy.<ref>{{cite journal|title=New York Magazine&nbsp;– Is Reagan Gala a Kennedy Snub?|website=Newyorkmetro.com|url=https://books.google.com/books?id=_eQCAAAAMBAJ&pg=PA12|date=December 8, 1980|page=12|issn=0028-7369|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429112753/https://books.google.com/books?id=_eQCAAAAMBAJ&pg=PA12|url-status=live}}</ref>{{Sfn|Farris|2013|p=196}} In 1985, Reagan presented Sinatra with the [[Presidential Medal of Freedom]], remarking, "His love of country, his generosity for those less fortunate{{nbsp}}... make him one of our most remarkable and distinguished Americans."<ref name=ESSAY />

In June 1984, Sinatra performed at the State Dinner in the White House honoring [[President of Sri Lanka|Sri Lankan President]] [[J. R. Jayewardene|J. R. Jayawardena]] at the invitation of Reagan.

[[File:Frank Sinatra visit to Israel (997009326703605171).jpg|thumb|Sinatra watching an [[Israel Defense Forces|IDF]] military parade during a visit to [[Israel]], 1962]]
Santopietro notes that Sinatra was a "lifelong sympathizer with [[Frank Sinatra and Jewish activism|Jewish causes]]."{{Sfn|Santopietro|2008|p=376}} He was awarded the [[Hollzer Memorial Award]] by the [[History of the Jews in Los Angeles|Los Angeles Jewish Community]] in 1949.{{sfn|Sinatra|1986|p=301}} He gave a series of concerts in Israel in 1962 and donated his entire $50,000 fee for appearing in a cameo role in ''[[Cast a Giant Shadow]]'' (1966) to the Youth Center in Jerusalem.{{Sfn|Santopietro|2008|p=376}} On November 1, 1972, he raised $6.5{{nbsp}}million in bond pledges for Israel,{{sfn|Sinatra|1986|p=231}} and was given the Medallion of Valor for his efforts.{{sfn|Sinatra|1986|p=307}} The Frank Sinatra Student Center at the [[Hebrew University of Jerusalem]] was dedicated in his name in 1978.{{sfn|Sinatra|1986|p=309}}

From his youth, Sinatra displayed sympathy for black Americans and worked both publicly and privately all his life to help the struggle for equal rights. He blamed racial prejudice on the parents of children.{{sfn|Summers|Swan|2010|p=138}} Sinatra played a major role in the [[Desegregation in the United States|desegregation]] of [[Nevada]] hotels and casinos in the 1950s and 1960s.<ref>{{cite book|title=Casino Journal: National ed, Volume 18&nbsp;– Desegregation of Nevada hotels and casinos|url=https://books.google.com/books?id=DWUsAQAAMAAJ|year=2005|publisher=Casino Journal of Nevada, Incorporated|pages=14–26|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429140713/https://books.google.com/books?id=DWUsAQAAMAAJ|url-status=live}}</ref> On January 27, 1961, Sinatra played a benefit show at Carnegie Hall for [[Martin Luther King Jr.]] and led his fellow Rat Pack members and Reprise label mates in boycotting hotels and casinos that refused entry to black patrons and performers. According to his son, Frank Jr., King sat weeping in the audience at one of his father's concerts in 1963 as Sinatra sang "[[Ol' Man River]]", a song from the musical ''[[Show Boat]]'' that is sung by a black American stevedore.<ref>{{cite news | work=Chicago Tribune | date=June 8, 1998 | url=https://www.chicagotribune.com/1998/06/08/race-relations-sinatras-way/ | title=Race Relations Sinatra's Way | access-date=January 10, 2015 | archive-date=September 23, 2015 | archive-url=https://web.archive.org/web/20150923181934/http://articles.chicagotribune.com/1998-06-08/news/9806080001_1_frank-sinatra-sinatra-fan-billie-holiday | url-status=live }}</ref> When he changed his political affiliations in 1970, Sinatra became less outspoken on racial issues.{{sfn|Kelley|1986|p=544}} Though he did much towards civil rights causes, it did not stop the occasional racial jibe from him and the other Rat Pack members toward Davis at concerts.<ref name="LAT99" />{{sfn|Sinatra|1986|p=133}}

== Death and funeral ==
[[File:Frank Sinatra.jpg|thumb|left|Sinatra's grave, as seen in 2004, located at [[Desert Memorial Park]] in Cathedral City, California (gravestone replaced in 2021)]]
During the final years of his life, Sinatra was in ill health and was frequently hospitalized for [[Cardiovascular disease|heart]] and [[breathing problems]], [[high blood pressure]], [[pneumonia]], and [[bladder cancer]]. He made no public appearances following a [[Myocardial infarction|heart attack]] in February 1997.<ref name="holden">{{cite news|last=Holden|first=Stephen|author-link=Stephen Holden|title=Frank Sinatra Dies at 82; Matchless Stylist of Pop|work=[[The New York Times]]|date=May 16, 1998 |url=https://www.nytimes.com/1998/05/16/movies/frank-sinatra-dies-at-82-matchless-stylist-of-pop.html|url-access=subscription|access-date=October 5, 2019|archive-url=https://web.archive.org/web/20210326201153/https://www.nytimes.com/1998/05/16/movies/frank-sinatra-dies-at-82-matchless-stylist-of-pop.html|archive-date=March 26, 2021}}</ref> A year later, on the night of May 14, 1998, Sinatra died in his sleep after suffering another heart attack at [[Cedars-Sinai Medical Center]] in Los Angeles, with his wife Barbara at his side. He was 82.<ref name=holden />{{sfn|Kelley|1986|p=Introduction xii}}<ref>{{Cite web |title=Frank Sinatra |url=https://findadeath.com/frank-sinatra/ |access-date=2024-01-09 |website=Celebrity Deaths: Findadeath |language=en-US}}</ref> Barbara encouraged Sinatra to "fight" while attempts were made to stabilize him, and reported that his final words were, "I'm losing."<ref name="farewell">{{cite news|url=http://www.cnn.com/SHOWBIZ/Music/9805/20/sinatra.funeral.early/index.html|title=Hollywood bids Sinatra last farewell|work=CNN|access-date=November 24, 2006|archive-date=October 4, 2018|archive-url=https://web.archive.org/web/20181004210136/http://www.cnn.com/SHOWBIZ/Music/9805/20/sinatra.funeral.early/index.html|url-status=live}}</ref> Sinatra's daughter, Tina, later wrote that she and her siblings had not been notified of their father's final hospitalization, and it was her belief that "the omission was deliberate. Barbara would be the grieving widow ''alone'' at her husband's side."{{sfn|Sinatra|Coplon|2000|p=286}} The night after Sinatra's death, the lights on the [[Empire State Building]] were turned blue, the lights at the [[Las Vegas Strip]] were dimmed in his honor, and the casinos stopped spinning for one minute.{{sfn|Kelley|1986|p=Introduction xii}}<ref name="BBCMay98">{{cite news|url=http://news.bbc.co.uk/2/hi/special_report/1998/05/98/sinatra/94366.stm|title=Empire State Building turns blue as silent tribute|work=BBC News|date=May 15, 1998|access-date=March 4, 2014|archive-date=August 2, 2019|archive-url=https://web.archive.org/web/20190802144734/http://news.bbc.co.uk/2/hi/special_report/1998/05/98/sinatra/94366.stm|url-status=live}}</ref> Significant increases in recording sales worldwide were reported by ''Billboard'' in the month of his death.<ref name="Billboard 0598">{{cite magazine|magazine=Billboard|title=Around The World, Retail Demand Is High For Sinatra's Recordings|url=https://books.google.com/books?id=fQ4EAAAAMBAJ&pg=PA93|date=May 30, 1998|page=93|issn=0006-2510|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429120132/https://books.google.com/books?id=fQ4EAAAAMBAJ&pg=PA93|url-status=live}}</ref>

Sinatra's funeral was held at the [[Church of the Good Shepherd (Beverly Hills, California)|Church of the Good Shepherd]] in [[Beverly Hills, California]], on May 20, 1998, with 400 mourners in attendance and thousands of fans outside.<ref name=finalcurtain>{{cite news|url=http://news.bbc.co.uk/2/hi/special_report/1998/05/98/sinatra/97196.stm|title=Special Report: Final curtain for Sinatra|date=May 20, 1998|access-date=May 15, 2008|work=BBC News|archive-date=July 20, 2019|archive-url=https://web.archive.org/web/20190720105119/http://news.bbc.co.uk/2/hi/special_report/1998/05/98/sinatra/97196.stm|url-status=live}}</ref> [[Gregory Peck]], [[Tony Bennett]], and Sinatra's son, Frank Jr., addressed the mourners, who included many people from entertainment.<ref name="farewell" /><ref name=finalcurtain />

Sinatra was buried in a blue business suit; his grave, adorned with mementos from family members, was next to his parents in [[Desert Memorial Park]] in [[Cathedral City, California]].{{sfnm|1a1=Sinatra|1a2=Coplon|1y=2000|1p=347|2a1=Brooks|2a2=Brooks|2y=2006|2pp=243–245}} The phrases "[[The Best Is Yet to Come]]", and "Beloved Husband & Father" were placed on Sinatra's modest grave marker.{{sfn|Wayne|2006|p=360}} Sinatra's gravestone was changed {{as of|2021|lc=y}} to read "Sleep Warm, Poppa", due to damage caused to the original gravestone under mysterious circumstances, according to the magazine ''Palm Springs Life''.<ref>{{Cite web |date=April 26, 2021 |title=Frank Sinatra Grave Marker Undergoes Mysterious Change |url=https://www.palmspringslife.com/frank-sinatra-grave/ |archive-url= https://web.archive.org/web/20210730163354/https://www.palmspringslife.com/frank-sinatra-grave/|archive-date= July 30, 2021|access-date=June 6, 2022 |website=Palm Springs Life |language=en-US}}</ref>

== Legacy and honors ==
{{See also|List of awards and nominations received by Frank Sinatra}}
[[File:7.4.10SinatraParkByLuigiNovi2.jpg|thumb|[[Frank Sinatra Park]] on the [[Hudson River Waterfront Walkway]], 4th of July, 2010]]
[[Robert Christgau]] referred to Sinatra as "the greatest singer of the 20th century".<ref name="Christgau">{{cite journal|last=Christgau|first=Robert|author-link=Robert Christgau|year=1998|url=http://www.robertchristgau.com/xg/music/sinatra-det.php|title=Frank Sinatra 1915–1998|journal=Details|access-date=January 10, 2015|archive-date=August 3, 2019|archive-url=https://web.archive.org/web/20190803210910/http://robertchristgau.com/xg/music/sinatra-det.php|url-status=live}}</ref> His popularity is matched only by [[Elvis Presley]], [[the Beatles]], and [[Michael Jackson]].<ref name="holden" /> For Santopietro, Sinatra was the "greatest male pop singer in the history of America",{{sfn|Santopietro|2008|p=456}} who amassed "unprecedented power onscreen and off", and "seemed to exemplify the common man, an ethnic twentieth-century American male who reached the 'top of the heap', yet never forgot his roots." Santopietro argues that Sinatra created his world, which he was able to dominate—his career was centered around power, perfecting the ability to capture an audience.{{sfn|Santopietro|2008|pp=76–78}}

[[Gus Levene]] commented that Sinatra's strength was that when it came to lyrics, telling a story musically, Sinatra displayed a "genius" ability and feeling, which with the "rare combination of voice and showmanship" made him the "original singer" which others who followed most tried to emulate.{{sfn|Granata|2003|p=68}} [[George Roberts (trombonist)|George Roberts]], a trombonist in Sinatra's band, remarked that Sinatra had a "charisma, or whatever it is about him, that no one else had."{{sfn|Granata|2003|p=32}} Biographer Arnold Shaw considered that "If Las Vegas had not existed, Sinatra could have invented it." He quoted reporter [[James Bacon (author)|James Bacon]] in saying that Sinatra was the "swinging image on which the town is built", adding that no other entertainer quite "embodied the glamour" associated with Las Vegas.{{sfn|Shaw|1982|p=48}} Sinatra is seen as one of the icons of the 20th century,{{sfn|Rojek|2004|p=1}} and has three stars on the [[Hollywood Walk of Fame]] for his work in film and music.<ref name=LATimes>{{cite news|url=http://projects.latimes.com/hollywood/star-walk/frank-sinatra|title=Hollywood Star Walk&nbsp;– Frank Sinatra|work=Los Angeles Times|access-date=March 4, 2014|archive-date=February 25, 2014|archive-url=https://web.archive.org/web/20140225015941/http://projects.latimes.com/hollywood/star-walk/frank-sinatra/|url-status=live}}</ref>

In Sinatra's native [[Hoboken, New Jersey|Hoboken]], he was awarded the [[Freedom of the City|Key to the City]] by [[Mayor of Hoboken, New Jersey|Mayor]] Fred M. De Sapio on October 30, 1947.<ref>{{Cite web |url=https://hoboken.pastperfectonline.com/photo/A971A97C-7385-40E8-816F-817857963620 |title=B+W copy photo of Mayor Fred DeSapio presenting Frank Sinatra with Key to the City at Hoboken City Hall, Hoboken, October 30, 1947. – Print, Photographic<!-- Bot generated title --> |access-date=June 5, 2020 |archive-date=June 5, 2020 |archive-url=https://web.archive.org/web/20200605232145/https://hoboken.pastperfectonline.com/photo/A971A97C-7385-40E8-816F-817857963620 |url-status=live }}</ref> In 2003, the city's main post office was rededicated in his honor.<ref>{{Cite web|url=https://archive.hudsonreporter.com/2003/05/27/start-spreading-the-news-post-office-renamed-to-honor-frank-sinatra/|title=Start spreading the news Post office renamed to honor Frank Sinatra|work=Hudson Reporter|date=May 27, 2003|access-date=December 12, 2021|archive-date=December 12, 2021|archive-url=https://web.archive.org/web/20211212163130/https://archive.hudsonreporter.com/2003/05/27/start-spreading-the-news-post-office-renamed-to-honor-frank-sinatra/|url-status=dead}}</ref> A bronze plaque, placed two years before Sinatra's death in 1998, marks the site of the house where he was born.<ref name="NJM" /> There is also a marker in front of [[Hoboken Historical Museum]], which has artifacts from his life and conducts Sinatra walking tours.<ref name="auto1">{{Cite web|url=https://www.nj.com/hudson/2021/06/ol-blue-eyes-returning-to-hoboken-in-december-and-hell-stay-awhile.html|title=Ol' Blue Eyes returning to Hoboken in December, and he'll stay awhile|first=Teri|last=West |newspaper=The Jersey Journal|date=June 16, 2021}}</ref> Frank Sinatra Drive runs parallel to the [[Hudson River Waterfront Walkway]]. On the waterfront is [[Frank Sinatra Park]], where a bronze plaque was placed in 1989 upon its opening.<ref name="NJM">{{Cite web|url=https://njmonthly.com/articles/historic-jersey/in-franks-footsteps-sinatra-walking-tour/|title=In Frank's Footsteps: The Sinatra Walking Tour|date=December 2, 2015|website=New Jersey Monthly}}</ref> In the Frank Sinatra Park, a {{convert|6|ft|m|adj=on}} tall bronze [[statue of Frank Sinatra|statue of Sinatra]] was dedicated in 2021 on December 12, Sinatra's birthday.<ref>{{Cite web|url=https://patch.com/new-jersey/hoboken/first-look-heres-frank-sinatra-statue-hoboken-waterfront|title=More Photos: New Frank Sinatra Statue On The Hoboken Waterfront|date=December 10, 2021|website=Hoboken, NJ Patch}}</ref><ref>{{Cite news|url=https://www.nj.com/hudson/2021/12/hoboken-to-unveil-tribute-to-hometown-legend-frank-sinatra-sunday.html|title=Hoboken to unveil tribute to hometown legend Frank Sinatra Sunday|first=Ron |last=Zeitlinger |newspaper = The Jersey Journal|date=December 9, 2021}}</ref><ref>City of Hoboken to unveil new Sinatra statue on Frank Sinatra's birthday
[https://hudsonreporter.com/2021/12/08/city-of-hoboken-to-unveil-new-sinatra-statue-on-frank-sinatras-birthday/] {{Webarchive|url=https://web.archive.org/web/20211210222630/https://hudsonreporter.com/2021/12/08/city-of-hoboken-to-unveil-new-sinatra-statue-on-frank-sinatras-birthday/|date=December 10, 2021}}</ref> A residence hall at [[Montclair State University]] in New Jersey was named in his honor.<ref name="MSU">{{cite web|title=Montclair State University Campus Map|url=http://www.montclair.edu/campus-map/?FontSize=10&w=950&h=494&x=2369.33333333&y=335&Zoom=0&Building=CLR|publisher=Montclair State University|date=August 18, 2010|access-date=August 18, 2010|archive-date=December 11, 2013|archive-url=https://web.archive.org/web/20131211071737/http://www.montclair.edu/campus-map/?FontSize=10&w=950&h=494&x=2369.33333333&y=335&Zoom=0&Building=CLR|url-status=live}}</ref> Other buildings named for Sinatra include the [[Frank Sinatra School of the Arts]] in [[Astoria, Queens]], the Frank Sinatra International Student Center at Israel's [[Hebrew University]] in Jerusalem dedicated in 1978,<ref name="JFed">{{cite web|title=Frank Sinatra's contribution to the Hebrew University|url=http://www.jewishfederations.org/page.aspx?id=82523|publisher=The Jewish Federations of North America|access-date=March 4, 2014|archive-url=https://web.archive.org/web/20140305042050/http://www.jewishfederations.org/page.aspx?id=82523|archive-date=March 5, 2014}}</ref> and the Frank Sinatra Hall at the [[USC School of Cinematic Arts]] in Los Angeles, California, dedicated in 2002.<ref name="USC">{{cite web|title=Frank Sinatra Hall&nbsp;– USC Cinematic Arts |url=http://cinema.usc.edu/facilities/sinatrahall.cfm |publisher=USC Cinematic Arts |access-date=March 4, 2014 |url-status=dead |archive-url=https://web.archive.org/web/20140226032837/http://cinema.usc.edu/facilities/sinatrahall.cfm |archive-date=February 26, 2014}}</ref> [[Wynn Resorts]]' [[Encore Las Vegas]] resort features a restaurant dedicated to Sinatra which opened in 2008.<ref name="Opening of Sinatra">{{cite web|title=Opening of Sinatra|publisher=Wynn Resorts|access-date=December 1, 2009|url=http://www.wynnpressroom.com/index.php?s=23&cat=27|archive-url=https://web.archive.org/web/20110718124553/http://www.wynnpressroom.com/index.php?s=23&cat=27|archive-date=July 18, 2011}}</ref> There are several streets and roads named in honor of Frank Sinatra in several states of the U.S.{{sfn|Sehlinger|Ridge|Castleman|2011|p=57}}

Various items of memorabilia from Sinatra's life and career, such as Frank Sinatra's awards, gold records, and various personal items, are displayed at [[University of Southern California|USC]]'s Frank Sinatra Hall in Los Angeles and at [[Wynn Resort]]'s Sinatra restaurant in Las Vegas.<ref name="USC" /><ref name="Opening of Sinatra" />
{{Multiple image|perrow=3|total_width=300
| image1 = Frank Sinatra star for Recording at 1637 Vine Street on Hollywood Walk of Fame 20220402 150342 HDR copy.jpg
| image2 = Frank Sinatra star for Television at 6538 Hollywood Boulevard on Hollywood Walk of Fame 20220402 145049 HDR copy.jpg
| image3 = Frank Sinatra star for Motion pictures at 1600 Vine Street on Hollywood Walk of Fame 20220402 152954 HDR copy.jpg
| footer = Sinatra's three stars for recording, television, and motion pictures on the [[Hollywood Walk of Fame]] in Los Angeles
}}
The [[United States Postal Service]] issued a 42-cent stamp in honor of Sinatra in May 2008, commemorating the tenth anniversary of his death.<ref name=stamp>{{cite press release|title=Postal Service to immortalize 'Ol' Blue Eyes' |url=http://about.usps.com/news/national-releases/2007/sr07_082.htm |publisher=United States Postal Service |date=December 5, 2007 |access-date=January 29, 2012 |archive-url=https://web.archive.org/web/20131206211527/http://www.reuters.com/article/2007/12/05/idUS202395%2B05-Dec-2007%2BPRN20071205 |archive-date=December 6, 2013 |url-status=dead}}</ref><ref name=sinatraasidol>{{cite news|title=Sinatra as Idol&nbsp;– Not Artist|url=https://www.wsj.com/articles/SB121063311685686579|date=May 13, 2008|access-date=May 15, 2008|last=Fusilli|first=Jim|work=The Wall Street Journal|archive-date=May 18, 2015|archive-url=https://web.archive.org/web/20150518201152/http://www.wsj.com/articles/SB121063311685686579|url-status=live}}</ref>
The [[United States Congress]] passed a resolution on May 20, 2008, designating May 13 as Frank Sinatra Day.<ref name=march13>{{cite news|title=Frank Sinatra Day|url=http://bono.house.gov/News/DocumentSingle.aspx?DocumentID=91885|date=May 20, 2008|last=Bono Mack|first=Mary|archive-url=https://web.archive.org/web/20120423011715/http://bono.house.gov/News/DocumentSingle.aspx?DocumentID=91885|archive-date=April 23, 2012|access-date=May 2, 2010|publisher=bono.house.gov}}</ref>

Sinatra received three [[Honorary Degree]]s during his lifetime. In May 1976, he was invited to speak at the [[University of Nevada, Las Vegas]] graduation commencement held at [[Sam Boyd Stadium]]. It was at this commencement that he was bestowed an Honorary Doctorate litterarum humanarum by the university.{{sfn|Moehring|2007|p=265}} During his speech, Sinatra stated that his education had come from "[[School of Hard Knocks|the school of hard knocks]]" and that "this is the first educational degree I have ever held in my hand. I will never forget what you have done for me today".<ref>{{cite web|title=The Back Story: And the Honor Goes To|url=http://www.unlv.edu/news/article/back-story-and-honor-goes|website=UNLV News Center|access-date=May 8, 2015|archive-date=September 5, 2015|archive-url=https://web.archive.org/web/20150905093531/https://www.unlv.edu/news/article/back-story-and-honor-goes|url-status=live}}</ref> In 1984 and 1985, Sinatra received an Honorary Doctorate of Fine Arts from [[Loyola Marymount University]] and an Honorary Doctorate of Engineering from the [[Stevens Institute of Technology]].<ref>{{cite news|title=Sinatra, others receive honorary college degrees|url=https://news.google.com/newspapers?id=hKgfAAAAIBAJ&pg=4850%2C4096358|access-date=May 8, 2015|agency=Associated Press|work=Gadsden Times|date=May 26, 1984|archive-date=October 30, 2021|archive-url=https://web.archive.org/web/20211030014953/https://news.google.com/newspapers?id=hKgfAAAAIBAJ&pg=4850%2C4096358|url-status=live}}</ref><ref>{{cite news|title=Our Towns; Frank Sinatra, Doctor of Engineering|url=https://www.nytimes.com/1985/05/23/nyregion/our-towns-frank-sinatra-doctor-of-engineering.html|access-date=May 8, 2015|work=The New York Times|date=May 23, 1985|archive-date=May 19, 2015|archive-url=https://web.archive.org/web/20150519005648/http://www.nytimes.com/1985/05/23/nyregion/our-towns-frank-sinatra-doctor-of-engineering.html|url-status=live}}</ref>

In 2023, ''[[Rolling Stone]]'' ranked Sinatra at No. 19 on their list of the 200 Greatest Singers of All Time.<ref>{{Cite magazine|date=January 1, 2023|title=The 200 Greatest Singers of All Time|url=https://www.rollingstone.com/music/music-lists/best-singers-all-time-1234642307/frank-sinatra-5-1234643186/|access-date=October 9, 2023|magazine=Rolling Stone|language=en-US}}</ref>

In 2024, a new road in North [[Bristol]] was named ''Sinatra Way'', to commemorate Sinatra's 1953 visit to [[Frenchay Hospital]], which used to sit at the site of a new housing development.<ref>{{cite news|url=https://www.bristolpost.co.uk/news/bristol-news/street-named-honour-frank-sinatras-9892189|title=Street named in honour of Frank Sinatra's famous Bristol hospital concert|last=Cork|first=Tristan|date=28 January 2025|work=[[Bristol Post|BristolLive]]|accessdate=28 January 2025}}</ref>

=== Tribute albums to Sinatra ===

* ''[[A Jazz Portrait of Frank Sinatra]]'' by [[Oscar Peterson]] (1959)
* ''Very Sinatra'' by [[Ruby Braff]] (1981)
* ''[[Perfectly Frank]]'' by [[Tony Bennett]] (1992)
* ''Voices in Standard'' by [[The Four Freshmen]] (1994)
* ''As I Remember It'' by [[Frank Sinatra, Jr.]] (1996)
* ''[[Manilow Sings Sinatra]]'' by [[Barry Manilow]] (1998)
* ''Sinatraland'' by [[Patrick Williams (composer)|Patrick Williams]] and His Big Band (1998)
* ''Blue Eyes Plays Ol' Blue Eyes'' by [[Si Zentner]] & Orchestra (1998)
* ''Keely Sings Sinatra'' by [[Keely Smith]] (2001)
* ''Michael Andrew Pays Tribute to Frank Sinatra'' by [[Michael Andrew (singer)|Michael Andrew]] (2002)
* [[Frank (Amy Winehouse album)|''Frank'']] by [[Amy Winehouse]] [2003] 
* ''Steve Lawrence Sings Sinatra'' by [[Steve Lawrence]] (2003)
* ''Plays Sinatra His Way'' by [[Joey DeFrancesco]] (2004)
* ''[[Allow Us to Be Frank]]'' by [[Westlife]] (2004)
* ''[[Songs of Sinatra]]'' by [[Steve Tyrell]] (2005)
* ''Blue Eyes Meets Bed-Stuy'' [[The Notorious B.I.G.]] & Frank Sinatra by Jon Moskowitz and Dj Cappel & Smitty (2005)
* ''L'allieva'' by [[Mina (Italian singer)|Mina]] (2005)
* ''[[Bolton Swings Sinatra]]'' by [[Michael Bolton]] (2006)
* ''Dear Mr. Sinatra'' by [[John Pizzarelli]] (2006)
* ''Ray Stevens Sings Sinatra...Say What??'' by [[Ray Stevens]] (2008)
* ''[[His Way, Our Way]]'' by various artists (2009)
* ''Cauby Sings Sinatra'' by [[Cauby Peixoto]] (2010)
* ''[[Sin-Atra]]'' a heavy metal tribute by various artists (2011)
*''Daniel Boaventura Sings Frank Sinatra (Ao Vivo)'' (2015)
* ''[[Let's Be Frank]]'' by [[Trisha Yearwood]] (2018)
* ''[[My Way (Willie Nelson album)|My Way]]'' by [[Willie Nelson]] (2018)
* ''[[That%27s Life (Willie Nelson album)|That’s Life]]'' by Willie Nelson (2021)
{{clear}}

== Film, television and stage portrayals ==
A television miniseries based on Sinatra's life, titled ''[[Sinatra (miniseries)|Sinatra]]'', was aired by CBS in 1992. The series was directed by [[James Steven Sadwith]], who won an Emmy Award for [[Primetime Emmy Award for Outstanding Directing for a Limited Series, Movie, or Dramatic Special|Outstanding Individual Achievement in Directing for a Miniseries or a Special]] and starred [[Philip Casnoff]] as Sinatra. ''Sinatra'' was written by [[Abby Mann]] and Philip Mastrosimone and produced by Sinatra's daughter, Tina.{{sfn|Roberts|2009|p=495}}

Sinatra has subsequently been portrayed on screen by [[Ray Liotta]] (''[[The Rat Pack (film)|The Rat Pack]]'', 1998),<ref>{{cite magazine|title=Sammy Davis, Jr., Frank Sinatra And Dean Martin's Legendary Friendship Revealed in TV Movie 'The Rat Pack'|magazine=Jet|url=https://books.google.com/books?id=RsQDAAAAMBAJ&pg=PA60|date=August 24, 1998|page=60|issn=0021-5996|access-date=November 25, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429091057/https://books.google.com/books?id=RsQDAAAAMBAJ&pg=PA60|url-status=live}}</ref> [[James Russo]] (''[[Stealing Sinatra]]'', 2003),{{Sfn|Lip|Prigge|2006|p=210}} [[Dennis Hopper]] (''[[The Night We Called It a Day (film)|The Night We Called It a Day]]'', 2003),<ref>{{cite web | url=https://variety.com/2003/film/reviews/the-night-we-called-it-a-day-1200539980/ | title=Review: 'The Night We Called it a Day' | work=Variety | date=August 13, 2003 | access-date=October 29, 2015 | last=Stratton | first=David | archive-date=November 8, 2012 | archive-url=https://web.archive.org/web/20121108175011/http://www.variety.com/review/VE1117921531/ | url-status=live }}</ref> and [[Robert Knepper]] (''[[My Way (2012 film)|My Way]]'', 2012),<ref>{{cite web|author=Van Hoeij, Boyd|url=https://variety.com/2012/film/markets-festivals/my-way-2-1117947315/|title=Review: 'My Way'|work=Variety|date=March 29, 2012|access-date=October 24, 2015|archive-date=November 26, 2015|archive-url=https://web.archive.org/web/20151126074640/http://variety.com/2012/film/markets-festivals/my-way-2-1117947315/|url-status=live}}</ref> and spoofed by [[Joe Piscopo]] and [[Phil Hartman]] on ''[[Saturday Night Live]]''.{{sfn|Fuchs|Prigozy|2007|p=138}} A biographical film directed by [[Martin Scorsese]] has long been planned.<ref>{{cite magazine|author=Fleming, Michael|url=https://deadline.com/2012/08/billy-ray-takes-on-sinatra-for-universal-and-martin-scorsese-318099/|title=Billy Ray Takes On 'Sinatra' For Universal And Martin Scorsese|magazine=Deadline|date=August 13, 2012|access-date=October 21, 2014|archive-date=September 24, 2014|archive-url=https://web.archive.org/web/20140924030754/http://deadline.com/2012/08/billy-ray-takes-on-sinatra-for-universal-and-martin-scorsese-318099/|url-status=live}}</ref> A 1998 episode of the BBC documentary series ''[[Arena (UK TV series)|Arena]]'', ''The Voice of the Century'', focused on Sinatra.<ref name=BBCArena>{{cite news|url=http://www.bbc.co.uk/programmes/b00rs3w6|title=BBC Four&nbsp;– Arena: Frank Sinatra: The Voice of the Century|work=BBC|access-date=March 9, 2014|archive-date=February 7, 2013|archive-url=https://web.archive.org/web/20130207000947/http://www.bbc.co.uk/programmes/b00rs3w6|url-status=live}}</ref> [[Alex Gibney]] directed a four-part biographical series on Sinatra, ''All or Nothing at All'', for HBO in 2015.<ref name=NYTApr15>{{cite news|url=https://www.nytimes.com/2015/04/02/arts/television/review-sinatra-alex-gibneys-new-hbo-documentary-explores-a-legend.html|title=Review: 'Sinatra', Alex Gibney's New HBO Documentary, Explores a Legend|author=Genzlinger, Neil|work=The New York Times|date=April 1, 2015|access-date=September 28, 2015|archive-date=October 24, 2015|archive-url=https://web.archive.org/web/20151024033855/http://www.nytimes.com/2015/04/02/arts/television/review-sinatra-alex-gibneys-new-hbo-documentary-explores-a-legend.html|url-status=live}}</ref> A musical tribute was aired on [[CBS]] television in December 2015 to mark Sinatra's centenary.<ref name=LATDec4>{{cite news|url=https://latimes.com/entertainment/music/posts/la-et-ms-frank-sinatra-100-concert-all-star-cbs-20151204-story.html|title=Stars align for Frank Sinatra 100th anniversary special Sunday on CBS|author=Lewis, Randy|work=Los Angeles Times|date=December 4, 2015|access-date=December 6, 2015|archive-date=December 5, 2015|archive-url=https://web.archive.org/web/20151205112551/http://www.latimes.com/entertainment/music/posts/la-et-ms-frank-sinatra-100-concert-all-star-cbs-20151204-story.html|url-status=live}}</ref> Sinatra was also portrayed by Rico Simonini in the 2018 feature film ''[[Frank & Ava]]'', which is based on a play by [[Willard Manus]].<ref>{{cite web|last=Paine|first=Herbert|title=BWW Review: FRANK & AVA ~ An Affair To Remember|date=March 3, 2018|publisher=[[BroadwayWorld]]|url=https://www.broadwayworld.com/phoenix/article/BWW-Review-FRANK-AVA-An-Affair-To-Remember-20180303|access-date=December 19, 2020|archive-date=May 6, 2021|archive-url=https://web.archive.org/web/20210506200951/https://www.broadwayworld.com/phoenix/article/BWW-Review-FRANK-AVA-An-Affair-To-Remember-20180303|url-status=live}}</ref><ref>{{cite web|last=Farber|first=Stephen|title='Frank & Ava': Film Review|date=December 6, 2018|work=[[The Hollywood Reporter]]|url=https://www.hollywoodreporter.com/review/frank-ava-review-1167364|access-date=December 19, 2020|archive-date=December 12, 2018|archive-url=https://web.archive.org/web/20181212021622/https://www.hollywoodreporter.com/review/frank-ava-review-1167364|url-status=live}}</ref> [[Creed (band)|Creed]] singer [[Scott Stapp]] also portrayed Sinatra in the 2024 feature film ''[[Reagan (2024 film)|Reagan]]'', a biopic of U.S. President [[Ronald Reagan]].<ref>{{cite news |url=https://www.billboard.com/articles/columns/tv-film/9501073/scott-stapp-frank-sinatra-ronald-reagan-biopic |title=Scott Stapp to Portray Frank Sinatra in Upcoming Ronald Reagan Biopic: Exclusive |last=Lipshutz |first=Jason |date=December 16, 2020 |magazine=Billboard |access-date=June 10, 2021 |archive-date=August 15, 2021 |archive-url=https://web.archive.org/web/20210815074640/https://www.billboard.com/articles/columns/tv-film/9501073/scott-stapp-frank-sinatra-ronald-reagan-biopic |url-status=live }}</ref><ref>{{cite news|url=https://www.billboard.com/music/music-news/scott-stapp-frank-sinatra-photo-ronald-reagan-film-1235763246/|title=See First Look at Scott Stapp Playing Frank Sinatra in Ronald Reagan Biopic|first=Rania|last=Anifos|publisher=Billboard|date=August 29, 2024|accessdate=August 30, 2024}}</ref> Martin Scorsese planned to make a film on Sinatra and his second wife Ava Gardner.<ref>{{cite web|url=https://variety.com/2024/film/news/martin-scorsese-frank-sinatra-biopic-dicaprio-jennifer-lawrence-1235973769/|title=Ageless Auteurs: Scorsese Eyes Frank Sinatra Biopic With Leonardo DiCaprio and Jennifer Lawrence, Spielberg Tackling UFO Movie and More|date=April 17, 2024 |publisher=Variety}}</ref>

Sinatra believed that Johnny Fontane, a mob-associated singer in [[Mario Puzo]]'s novel ''[[The Godfather (novel)|The Godfather]]'' (1969), was based on him. Puzo wrote in 1972 that when the author and singer met in [[Chasen's]], Sinatra "started to shout abuse", calling Puzo a "pimp" and threatening violence. [[Francis Ford Coppola]], director of the [[The Godfather|film adaptation]], said in the [[audio commentary]] that "Obviously Johnny Fontane was inspired by a kind of Frank Sinatra character".<ref name="parker20151211">{{Cite news |url=https://www.hollywoodreporter.com/news/sinatra-at-100-was-a-844595 |title=The Time Frank Sinatra Berated Mario Puzo For His Assumed Likeness in 'The Godfather' |last=Parker |first=Ryan |date=December 11, 2015 |work=The Hollywood Reporter |access-date=December 28, 2018 |archive-date=December 29, 2018 |archive-url=https://web.archive.org/web/20181229075552/https://www.hollywoodreporter.com/news/sinatra-at-100-was-a-844595 |url-status=live }}</ref>

In 2023, a biopic jukebox stage musical titled ''[[Sinatra: The Musical]]'' by [[Joe DiPietro]] premiered at the [[Birmingham Repertory Theatre]] starring Tony Award-winning actor [[Matt Doyle (actor)|Matt Doyle]] as Sinatra.<ref>{{Cite web |last=Willman |first=Chris |date=July 11, 2023 |title='Sinatra the Musical', Set to Premiere in U.K., Casts Tony Winner Matt Doyle as Ol' Blue Eyes |url=https://variety.com/2023/music/news/sinatra-musical-casts-tony-winner-matt-doyle-frank-england-1235666711/ |access-date=November 2, 2024 |website=Variety |language=en-US}}</ref>

== Discography ==
{{Main|Frank Sinatra discography|List of songs recorded by Frank Sinatra}}

'''Studio albums'''
{{div col}}
* ''[[The Voice of Frank Sinatra]]'' (1946)
* ''[[Songs by Sinatra]]'' (1947)
* ''[[Christmas Songs by Sinatra]]'' (1948)
* ''[[Frankly Sentimental]]'' (1949)
* ''[[Dedicated to You (Frank Sinatra album)|Dedicated to You]]'' (1950)
* ''[[Swing and Dance with Frank Sinatra|Sing and Dance with Frank Sinatra]]'' (1950)
* ''[[Songs for Young Lovers]]'' (1954)
* ''[[Swing Easy!]]'' (1954)
* ''[[In the Wee Small Hours]]'' (1955)
* ''[[Songs for Swingin' Lovers!]]'' (1956)
* ''[[Close to You (Frank Sinatra album)|Close to You]]'' (1957)
* ''[[A Swingin' Affair!]]'' (1957)
* ''[[Where Are You? (Frank Sinatra album)|Where Are You?]]'' (1957)
* ''[[A Jolly Christmas from Frank Sinatra]]'' (1957)
* ''[[Come Fly with Me (Frank Sinatra album)|Come Fly with Me]]'' (1958)
* ''[[Frank Sinatra Sings for Only the Lonely]]'' (1958)
* ''[[Come Dance with Me! (album)|Come Dance with Me!]]'' (1959)
* ''[[No One Cares]]'' (1959)
* ''[[Nice 'n' Easy]]'' (1960)
* ''[[Sinatra's Swingin' Session!!!]]'' (1961)
* ''[[Ring-a-Ding-Ding!]]'' (1961)
* ''[[Come Swing with Me!]]'' (1961)
* ''[[Sinatra Swings|Swing Along With Me]]'' (1961)
* ''[[I Remember Tommy]]'' (1961)
* ''[[Sinatra and Strings]]'' (1962)
* ''[[Point of No Return (Frank Sinatra album)|Point of No Return]]'' (1962)
* ''[[Sinatra and Swingin' Brass]]'' (1962)
* ''[[All Alone (Frank Sinatra album)|All Alone]]'' (1962)
* ''[[Sinatra Sings Great Songs from Great Britain]]'' (1962)
* ''[[The Concert Sinatra]]'' (1963)
* ''[[Sinatra's Sinatra]]'' (1963)
* ''[[Sinatra Sings Days of Wine and Roses, Moon River, and Other Academy Award Winners]]'' (1964)
* ''[[Softly, as I Leave You (album)|Softly, as I Leave You]]'' (1964)
* ''[[September of My Years]]'' (1965)
* ''[[Sentimental Journey (song)|Sentimental Journey]]'' (1965)
* ''[[My Kind of Broadway]]'' (1965)
* ''[[A Man and His Music]]'' (1965)
* ''[[Moonlight Sinatra]]'' (1966)
* ''[[Strangers in the Night (Frank Sinatra album)|Strangers in the Night]]'' (1966)
* ''[[That's Life (Frank Sinatra album)|That's Life]]'' (1966)
* ''[[The World We Knew]]'' (1967)
* ''[[Cycles (Frank Sinatra album)|Cycles]]'' (1968)
* ''[[My Way (Frank Sinatra album)|My Way]]'' (1969)
* ''[[A Man Alone (album)|A Man Alone]]'' (1969)
* ''[[Watertown (album)|Watertown]]'' (1970)
* ''[[Ol' Blue Eyes Is Back]]'' (1973)
* ''[[Some Nice Things I've Missed]]'' (1974)
* ''[[Trilogy: Past Present Future]]'' (1980)
* ''[[She Shot Me Down]]'' (1981)
* ''[[L.A. Is My Lady]]'' (1984)
* ''[[Duets (Frank Sinatra album)|Duets]]'' (1993)
* ''[[Duets II (Frank Sinatra album)|Duets II]]'' (1994)
{{div col end}}

'''Collaboration albums'''
* ''[[Sinatra–Basie: An Historic Musical First]]'' <small>with Count Basie</small> (1962)
* ''[[America, I Hear You Singing]]'' <small>with Bing Crosby and Fred Waring</small> (1964)
* ''[[It Might as Well Be Swing]]'' <small>with Count Basie</small> (1964)
* ''[[12 Songs of Christmas (Frank Sinatra, Bing Crosby and Fred Waring album)|12 Songs of Christmas]]'' <small>with Bing Crosby and Fred Waring</small> (1964)
* ''[[Francis Albert Sinatra & Antonio Carlos Jobim]]'' <small>with Antonio Carlos Jobim</small> (1967)
* ''[[Francis A. & Edward K.]]'' <small>with Duke Ellington</small> (1968)
* ''[[The Sinatra Family Wish You a Merry Christmas]]'' <small>with Frank Sinatra Jr., Nancy Sinatra and Tina Sinatra</small> (1968)
* ''[[Sinatra & Company]]'' <small>with Antonio Carlos Jobim</small> (1971)

== See also ==
* [[Frank Sinatra bibliography]]
* [[Frank Sinatra's recorded legacy]]
* [[The Frank Sinatra Show (radio program)|''The Frank Sinatra Show'' (radio program)]]

== Notes ==
{{Notelist}}

== References ==
{{Reflist}}

== Sources ==
{{Refbegin|30em}}
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* {{cite book|last=Lamb|first=David|title=The Africans|url=https://books.google.com/books?id=GEVnODW09HMC|date=August 24, 2011|publisher=Knopf Doubleday Publishing Group|isbn=978-0-307-79792-6|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429145121/https://books.google.com/books?id=GEVnODW09HMC|url-status=live}}
* {{cite book|last=Larkin|first=Colin|title=The Virgin Encyclopedia of Fifties Music|url=https://books.google.com/books?id=kGkZAQAAIAAJ|year=2002|publisher=Virgin Books|isbn=978-1-85227-937-0|access-date=October 20, 2015|archive-date=April 24, 2016|archive-url=https://web.archive.org/web/20160424145610/https://books.google.com/books?id=kGkZAQAAIAAJ|url-status=live}}
* {{cite book|last=Lees|first=Gene|title=Singers and the Song II|year=1998|publisher=Oxford University Press|isbn=978-0-19-511556-7 }}
* {{cite book|last=Levinson|first=Peter J.|title=September in the Rain: The Life of Nelson Riddle|url=https://archive.org/details/septemberinrainl00levi|year=2001|publisher=Billboard Books|isbn=978-0-8230-7672-7}}
* {{cite book|last=Levinson|first=Peter J.|title=Tommy Dorsey: Livin' in a Great Big Way, a Biography|url=https://books.google.com/books?id=644DvSdKKrAC&pg=PA161|date=2009|publisher=Da Capo Press, Incorporated|isbn=978-0-7867-3494-8|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429135840/https://books.google.com/books?id=644DvSdKKrAC&pg=PA161|url-status=live}}
* {{cite book|last1=Land|first1=Barbara|last2=Land|first2=Myrick|title=A Short History of Las Vegas|url=https://books.google.com/books?id=T6O2fMmPfCcC&pg=PA148|year=2004|publisher=University of Nevada Press|isbn=978-0-87417-564-6|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429105643/https://books.google.com/books?id=T6O2fMmPfCcC&pg=PA148|url-status=live}}
* {{cite book|last1=Lehmann|first1=Bob|last2=Blanck|first2=Bob|title=San Gorgonio Search and Rescue Team|url=https://books.google.com/books?id=Aavq5g4K-PAC&pg=PA100|date=April 30, 2008|publisher=Arcadia Publishing|isbn=978-0-7385-5576-8|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429073712/https://books.google.com/books?id=Aavq5g4K-PAC&pg=PA100|url-status=live}}
* {{cite book|last1=Lip|first1=Tony|last2=Prigge|first2=Steven|title=Shut Up and Eat!: Mangia with Family Recipes and Stories from Your Favorite Italian-American Stars|url=https://books.google.com/books?id=jGavsshM0F0C|date=October 3, 2006|publisher=Penguin Group USA|isbn=978-0-425-21177-9|access-date=November 25, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429125105/https://books.google.com/books?id=jGavsshM0F0C|url-status=live}}
* {{cite book|last1=Lonstein|first1=Albert I.|last2=Marino|first2=Vito R.|title=The Compleat Sinatra: Disgography {{sic|nolink=y}} Filmography, Television Appearances, Motion Picture Appearances, Radio Appearances, Concert Appearances, Stage Appearances|url=https://books.google.com/books?id=svRCAAAAIAAJ|year=1970|publisher=Cameron Publications|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429140306/https://books.google.com/books?id=svRCAAAAIAAJ|url-status=live}}
* {{cite book|last=Marill|first=Alvin H.|title=The complete films of Edward G. Robinson|url=https://books.google.com/books?id=8H8dAQAAIAAJ|year=1990|publisher=Carol Publishing Group|isbn=978-0-8065-1181-8|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429135940/https://books.google.com/books?id=8H8dAQAAIAAJ|url-status=live}}
* {{cite book|last=McGuiggan|first=Amy Whorf|title=Take Me Out to the Ball Game: The Story of the Sensational Baseball Song|url=https://archive.org/details/takemeouttoballg00amyw/page/86|year=2009|publisher=U of Nebraska Press|isbn=978-0-8032-1891-8|page=[https://archive.org/details/takemeouttoballg00amyw/page/86 86]}}
* {{cite book|last=McNally|first=Karen|title=When Frankie Went to Hollywood: Frank Sinatra and American Male Identity|url=https://books.google.com/books?id=erZCCQAAQBAJ&pg=PA49|date=June 12, 2015|publisher=University of Illinois Press|isbn=978-0-252-09820-8|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429120042/https://books.google.com/books?id=erZCCQAAQBAJ&pg=PA49|url-status=live}}
* {{cite book|last=Mirtle|first=Jack|title=The Music of Billy May: A Discography|url=https://books.google.com/books?id=QQarAAAAIAAJ|date=January 1, 1998|publisher=Greenwood Press|isbn=978-0-313-30739-3|access-date=November 25, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429125310/https://books.google.com/books?id=QQarAAAAIAAJ|url-status=live}}
* {{cite book|last1=Moehring|first1=Eugene P.|title=The University of Nevada, Las Vegas: A History|date=2007|publisher=University of Nevada Press}}
* {{cite book|last=Morrell|first=David|title=Frank Sinatra: The Artist and His Music|url=https://books.google.com/books?id=G3KUAgAAQBAJ&pg=PT40|date=January 24, 2013|publisher=David Morrell|isbn=978-1-937760-24-3|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429145222/https://books.google.com/books?id=G3KUAgAAQBAJ&pg=PT40|url-status=live}}
* {{cite book|last=Moser|first=Margaret|title=Movie Stars Do the Dumbest Things|url=https://books.google.com/books?id=_66gMFl2IjAC&pg=RA2-PA1959|date=April 1, 2011|publisher=St. Martin's Press|isbn=978-1-4299-7837-8|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429145103/https://books.google.com/books?id=_66gMFl2IjAC&pg=RA2-PA1959|url-status=live}}
* {{cite book|last=Nachman|first=Gerald|author-link=Gerald Nachman (journalist)|url=https://books.google.com/books?id=hpywoSI2au4C&pg=PA170|title=Raised on Radio|publisher=University of California Press|year=2000|isbn=978-0-520-22303-5|access-date=October 6, 2015|archive-date=April 26, 2016|archive-url=https://web.archive.org/web/20160426103935/https://books.google.com/books?id=hpywoSI2au4C&pg=PA170|url-status=live}}
* {{cite book|last=Newton|first=Michael|title=The FBI Encyclopedia|url=https://books.google.com/books?id=R73eCQAAQBAJ&pg=PR7|date=October 31, 2003|publisher=McFarland|isbn=978-0-7864-6620-7|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429120102/https://books.google.com/books?id=R73eCQAAQBAJ&pg=PR7|url-status=live}}
* {{cite book|last=Nimmo|first=Harry|title=The Andrews Sisters: A Biography and Career Record|url=https://books.google.com/books?id=YJxeFWmNc_EC&pg=PA228|year=2004|publisher=McFarland|isbn=978-0-7864-1731-5|access-date=October 20, 2015|archive-date=April 26, 2016|archive-url=https://web.archive.org/web/20160426080241/https://books.google.com/books?id=YJxeFWmNc_EC&pg=PA228|url-status=live}}
* {{cite book|last=O'Brien|first=Daniel|title=The Frank Sinatra Film Guide|url=https://books.google.com/books?id=zm4dAQAAIAAJ|year=1998|publisher=Batsford|isbn=978-0-7134-8418-2|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429125113/https://books.google.com/books?id=zm4dAQAAIAAJ|url-status=live}}
* {{cite book|last=O'Brien|first=Daniel|title=The Frank Sinatra Film Guide|url=https://books.google.com/books?id=9k2_CAAAQBAJ&pg=PT221|date=October 30, 2014|publisher=Pavilion Books|isbn=978-1-84994-250-8|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429135557/https://books.google.com/books?id=9k2_CAAAQBAJ&pg=PT221|url-status=live}}
* {{cite book|last=Osborne|first=Richard|title=Vinyl: A History of the Analogue Record|url=https://books.google.com/books?id=-B2rBAAAQBAJ&pg=PA98|date=July 28, 2014|publisher=Ashgate Publishing, Ltd.|isbn=978-1-4724-3433-3|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429113222/https://books.google.com/books?id=-B2rBAAAQBAJ&pg=PA98|url-status=live}}
* {{cite book|last1=Peters|first1=Richard|last2=O'Brien|first2=Ed|last3=Sayers|first3=Scott P.|title=The Frank Sinatra Scrapbook: His Life and Times in Words and Pictures|url=https://books.google.com/books?id=W5dVPwAACAAJ|year=1982|publisher=Pop Universal|isbn=978-0-285-62539-6|access-date=October 20, 2015|archive-date=April 25, 2016|archive-url=https://web.archive.org/web/20160425201917/https://books.google.com/books?id=W5dVPwAACAAJ|url-status=live}}
* {{cite book|last1=Petkov|first1=Steven|last2=Mustazza|first2=Leonard|title=The Frank Sinatra Reader|url=https://archive.org/details/franksinatraread00petk|year=1995|publisher=Oxford University Press|isbn=978-0-19-509531-9}}
* {{cite book|last1=Quirk|first1=Lawrence J.|last2=Schoell|first2=William|url=https://books.google.com/books?id=F5bY3F5Vm28C|title=The Rat Pack: Neon Nights with the Kings of Cool|year=1999|publisher=Harper Collins|isbn=978-0-380-73222-7|access-date=October 13, 2015|archive-date=August 1, 2020|archive-url=https://web.archive.org/web/20200801193320/https://books.google.com/books?id=F5bY3F5Vm28C|url-status=live}}
* {{cite book|last1=Rees|first1=Dafydd|last2=Crampton|first2=Luke|title=Rock Stars Encyclopedia|url=https://archive.org/details/rockstarsencyclo00rees|year=1999|publisher=DK Pub.|isbn=978-0-7894-4613-8}}
* {{cite book|last=Ridgeway|first=John|title=The Sinatra File|publisher=John Ridgeway Books|year=1977}}
* {{cite book|last=Roberts|first=Jerry|title=Encyclopedia of Television Film Directors|url=https://books.google.com/books?id=kW8j6sHvrewC&pg=PA495|date=June 5, 2009|publisher=Scarecrow Press|isbn=978-0-8108-6378-1|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429125233/https://books.google.com/books?id=kW8j6sHvrewC&pg=PA495|url-status=live}}
* {{cite book|last=Roby|first=Steven|title=Becoming Jimi Hendrix: From Southern Crossroads to Psychedelic London, the Untold Story of a Musical Genius|url=https://archive.org/details/becomingjimihend00roby|url-access=registration|page=[https://archive.org/details/becomingjimihend00roby/page/111 111]|date=August 31, 2010|publisher=Da Capo Press|isbn=978-0-306-81945-2}}
* {{cite book|last=Rojek|first=Chris|url=https://books.google.com/books?id=F4DEdXSMYikC&pg=PA40|year=2004|publisher=Polity|title=Frank Sinatra|isbn=978-0-7456-3090-8|access-date=August 31, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429120038/https://books.google.com/books?id=F4DEdXSMYikC&pg=PA40|url-status=live}}
* {{cite book|last=Roman|first=James|title=Chronicles of Old Las Vegas: Exposing Sin City's High-Stakes History|url=https://books.google.com/books?id=wwpMBAAAQBAJ&pg=PA235|date=October 1, 2011|publisher=Museyon|isbn=978-1-938450-02-0|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429112516/https://books.google.com/books?id=wwpMBAAAQBAJ&pg=PA235|url-status=live}}
* {{cite book|last=Rotella|first=Mark|url=https://books.google.com/books?id=zoYnI2TZg1kC&q=sinatra+frankie+satin&pg=PT81|title=Amore: The Story of Italian American Song|publisher=Macmillan|year=2010|isbn=978-1-4299-7847-7|access-date=October 17, 2020|archive-date=August 17, 2021|archive-url=https://web.archive.org/web/20210817003928/https://books.google.com/books?id=zoYnI2TZg1kC&q=sinatra+frankie+satin&pg=PT81|url-status=live}}
* {{cite book|last=Sackett|first=Susan|title=Hollywood Sings!: An Inside Look at Sixty Years of Academy Award-nominated Songs|url=https://books.google.com/books?id=Fhg5AQAAIAAJ|year=1995|publisher=Billboard Books|isbn=978-0-8230-7623-9|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429125209/https://books.google.com/books?id=Fhg5AQAAIAAJ|url-status=live}}
* {{cite book|last=Sann|first=Paul|title=Fads, Follies, and Delusions of the American People /by Paul Sann|url=https://books.google.com/books?id=6g5CAAAAIAAJ|year=1967|publisher=Crown Publishers|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429140146/https://books.google.com/books?id=6g5CAAAAIAAJ|url-status=live}}
* {{cite book|last=Santopietro|first=Tom|title=Sinatra in Hollywood|url=https://archive.org/details/sinatrainhollywo00sant_0|date=November 11, 2008|publisher=St. Martin's Press|isbn=978-0-312-36226-3}}
* {{cite book|last1=Sehlinger|first1=Bob|last2=Ridge|first2=Menasha|last3=Castleman|first3=Deke|title=The Unofficial Guide to Las Vegas 2012|url=https://books.google.com/books?id=3vCE2_1dY4cC&pg=PA57|date=August 8, 2011|publisher=John Wiley & Sons|isbn=978-1-118-14345-2|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429120009/https://books.google.com/books?id=3vCE2_1dY4cC&pg=PA57|url-status=live}}
* {{cite book|last=Sforza|first=John|title=Swing It!: The Andrews Sisters Story|url=https://books.google.com/books?id=HqkeBgAAQBAJ&pg=PA80|date=February 5, 2015|publisher=University Press of Kentucky|isbn=978-0-8131-4897-7|access-date=October 20, 2015|archive-date=April 28, 2016|archive-url=https://web.archive.org/web/20160428054158/https://books.google.com/books?id=HqkeBgAAQBAJ&pg=PA80|url-status=live}}
* {{cite book|last=Shaw|first=Arnold|title=Sinatra: retreat of the romantic|url=https://books.google.com/books?id=WvU5AQAAIAAJ|date=June 1968|publisher=W. H. Allen|isbn=978-0-491-00161-8|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429084534/https://books.google.com/books?id=WvU5AQAAIAAJ|url-status=live}}
* {{cite book|last=Shaw|first=Arnold|title=Sinatra, the entertainer|url=https://books.google.com/books?id=KtS52rW0g-cC|year=1982|publisher=Delilah|isbn=978-0-933328-43-3|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429135754/https://books.google.com/books?id=KtS52rW0g-cC|url-status=live}}
* {{cite book|last=Sheridan|first=John Harris|title=Howard Hughes: The Las Vegas Years: The Women, the Mormons, the Mafia|url=https://books.google.com/books?id=5YHMr6LRpocC&pg=PA52|date=September 6, 2011|publisher=AuthorHouse|isbn=978-1-4634-0693-6|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429082954/https://books.google.com/books?id=5YHMr6LRpocC&pg=PA52|url-status=live}}
* {{cite book | last=Sifakis | first=Carl | url=https://books.google.com/books?id=jgCpxTpPCPcC | title=The Mafia Encyclopedia | publisher=Infobase Publishing | isbn=978-0-8160-6989-7 | date=January 1, 2005 | access-date=August 28, 2017 | archive-date=January 25, 2016 | archive-url=https://web.archive.org/web/20160125093749/https://books.google.com/books?id=jgCpxTpPCPcC | url-status=live }}
* {{cite book|last=Silva|first=Luiz Carlos do Nascimento|title=Put Your Dreams Away: A Frank Sinatra Discography|url=https://books.google.com/books?id=yqth52rImHQC&pg=PA12|date=January 1, 2000|publisher=Greenwood Publishing Group|isbn=978-0-313-31055-3|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429140239/https://books.google.com/books?id=yqth52rImHQC&pg=PA12|url-status=live}}
* {{cite book|last=Sinatra|first=Barbara|title=Lady Blue Eyes: My Life with Frank Sinatra|url=https://books.google.com/books?id=PbTidwc4JnAC&pg=PT274|year=2011|publisher=Random House|isbn=978-1-4464-7288-0|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429073855/https://books.google.com/books?id=PbTidwc4JnAC&pg=PT274|url-status=live}}
* {{cite book|last=Sinatra|first=Nancy|title=Frank Sinatra: An American Legend|url=https://archive.org/details/franksinatraamer00sina|publisher=General Publishing Group|year=1995|isbn=978-1-881649-68-7}}
* {{cite book|last=Sinatra|first=Nancy|title=Frank Sinatra, My Father|url=https://archive.org/details/franksinatra00nanc/page/24|year=1986|publisher=Simon and Schuster|isbn=978-0-671-62508-5|page=[https://archive.org/details/franksinatra00nanc/page/24 24]}}
* {{cite book|last1=Sinatra|first1=Tina|last2=Coplon|first2=Jeff|title=My Father's Daughter: A Memoir|year=2000|publisher=Simon & Schuster|location=New York|isbn=0-684-87076-2}}
* {{cite book|last=Sirvaitis|first=Karen|title=The European American Experience|url=https://archive.org/details/europeanamerican0000sirv|url-access=registration|page=[https://archive.org/details/europeanamerican0000sirv/page/23 23]|date=August 1, 2010|publisher=Twenty-First Century Books|isbn=978-0-7613-4088-1}}
* {{cite book|last=Small|first=Pauline|title=Sophia Loren: Moulding the Star|url=https://books.google.com/books?id=4QhnLOpcLfcC&pg=PA59|year=2009|publisher=Intellect Books|isbn=978-1-84150-234-2|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429074412/https://books.google.com/books?id=4QhnLOpcLfcC&pg=PA59|url-status=live}}
* {{cite book|last=Smith|first=Chris|title=One Hundred and One Albums that Changed Popular Music|url=https://books.google.com/books?id=G4mP7u6mPdkC&pg=PR18|year=2009|publisher=Oxford University Press|isbn=978-0-19-537371-4|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429145215/https://books.google.com/books?id=G4mP7u6mPdkC&pg=PR18|url-status=live}}
* {{cite book|last=Smith|first=Martin|title=Frank Sinatra: When Ol' Blue Eyes was a Red|url=https://books.google.com/books?id=qnrRAAAACAAJ|year=2005|publisher=Redwords|isbn=978-1-905192-02-1|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429100350/https://books.google.com/books?id=qnrRAAAACAAJ|url-status=live}}
* {{cite book|last=Sonneborn|first=Liz|title=A to Z of American Women in the Performing Arts|url=https://books.google.com/books?id=Yf2741A_BkYC&pg=PA79|date=January 1, 2002|publisher=Infobase Publishing|isbn=978-1-4381-0790-5|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429084158/https://books.google.com/books?id=Yf2741A_BkYC&pg=PA79|url-status=live}}
* {{cite book|last1=Summers|first1=Anthony|last2=Swan|first2=Robbyn|title=Sinatra: The Life|url=https://books.google.com/books?id=R5SddF7R6x4C|year=2010|publisher=Transworld|isbn=978-1-4070-6890-9|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429140401/https://books.google.com/books?id=R5SddF7R6x4C|url-status=live}}
* {{cite book|last=Terrace|first=Vincent|title=Radio Programs, 1924–1984: A Catalog of More Than 1800 Shows|url=https://books.google.com/books?id=nIiACgAAQBAJ&pg=PA287|date=November 1, 1998|publisher=McFarland|isbn=978-0-7864-4513-4|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429125144/https://books.google.com/books?id=nIiACgAAQBAJ&pg=PA287|url-status=live}}
* {{cite book|last=Terrace|first=Vincent|title=Television Specials: 5,336 Entertainment Programs, 1936–2012, 2d ed.|url=https://books.google.com/books?id=Of0QAAAAQBAJ&pg=PA157|date=June 19, 2013|publisher=McFarland|isbn=978-1-4766-1240-9|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429140138/https://books.google.com/books?id=Of0QAAAAQBAJ&pg=PA157|url-status=live}}
* {{cite book|last=Thomas|first=Evan|title=Robert Kennedy: His Life|url=https://books.google.com/books?id=ofXSLln9a3QC&pg=PA169|date=February 5, 2013|publisher=Simon and Schuster|isbn=978-1-4767-3456-9|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429082613/https://books.google.com/books?id=ofXSLln9a3QC&pg=PA169|url-status=live}}
* {{cite book|last=Travis|first=Dempsey J.|title=The FBI Files: On the Tainted and the Damned|url=https://books.google.com/books?id=RGMsAQAAMAAJ|date=December 1, 2001|publisher=Urban Research Pr|isbn=978-0-941484-32-9|access-date=November 25, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429120148/https://books.google.com/books?id=RGMsAQAAMAAJ|url-status=live}}
* {{cite book|last=Turner|first=John Frayn|title=Frank Sinatra|url=https://archive.org/details/franksinatra00john/page/93|date=January 1, 2004|publisher=Taylor Trade Publications|isbn=978-1-58979-145-9|page=[https://archive.org/details/franksinatra00john/page/93 93]}}
* {{cite book|last=Tyler|first=Don|title=Hit Songs, 1900–1955: American Popular Music of the Pre-rock Era|url=https://books.google.com/books?id=yycKAQAAMAAJ|date=January 1, 2007|publisher=McFarland|isbn=978-0-7864-2946-2|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429145230/https://books.google.com/books?id=yycKAQAAMAAJ|url-status=live}}
* {{cite book|last1=Waldman|first1=Carl|last2=Donovan|first2=Jim|title=Forever Sinatra: A Celebration in Words & Images|url=https://books.google.com/books?id=zAJZm7LDUSUC|date=February 1, 1999|publisher=Legends Press|isbn=978-0-9668136-0-9|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429102418/https://books.google.com/books?id=zAJZm7LDUSUC|url-status=live}}
* {{cite book|last=Wayne|first=Jane Ellen|title=Ava Gardner: Her Life and Loves|url=https://books.google.com/books?id=UF2-vLvja1IC&pg=PP15|year=2004|publisher=Robson|isbn=978-1-86105-785-3|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429144941/https://books.google.com/books?id=UF2-vLvja1IC&pg=PP15|url-status=live}}
* {{cite book|last=Wayne|first=Jane|title=The Leading Men of MGM|url=https://books.google.com/books?id=YqfsLfqfLmYC&pg=PA360|date=April 16, 2006|publisher=Da Capo Press|isbn=978-0-7867-1768-2|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429140442/https://books.google.com/books?id=YqfsLfqfLmYC&pg=PA360|url-status=live}}
* {{cite book|last=Weatherford|first=Mike|title=Cult Vegas: The Weirdest! the Wildest! the Swingin'est Town on Earth!|url=https://books.google.com/books?id=y3a3l0zST68C&pg=PA14|date=January 1, 2001|publisher=Huntington Press Inc|isbn=978-0-929712-71-0|access-date=November 25, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429084222/https://books.google.com/books?id=y3a3l0zST68C&pg=PA14|url-status=live}}
* {{cite book |last=Whitburn |first=Joel |date=1986 |title=Pop Memories 1890–1954 |location=Menomonee Falls, Wisconsin |publisher=Record Research, Inc. |isbn=0-89820-083-0 |url=https://archive.org/details/joelwpopmemories00whit }}
* {{cite book|last=Whitburn|first=Joel|title=Joel Whitburn's top pop albums, 1955–2001|url=https://archive.org/details/joelwhitburnstop00whitbu|year=2001|publisher=Record Research|isbn=978-0-89820-147-5}}
* {{cite book|last1=Wilson|first1=Colin|last2=Wilson|first2=Damon|title=Scandal!: An Explosive Exposé of the Affairs, Corruption and Power Struggles of the Rich and Famous|url=https://books.google.com/books?id=GM2_O5dJ6GUC&pg=PT129|date=May 31, 2011|publisher=Ebury Publishing|isbn=978-0-7535-4732-8|access-date=October 20, 2015|archive-date=April 29, 2016|archive-url=https://web.archive.org/web/20160429113109/https://books.google.com/books?id=GM2_O5dJ6GUC&pg=PT129|url-status=live}} <!-- Note the only edition available for full view at Google is an e-book with no page numbers. -->
* {{cite book|last=Wood|first=Ean|title=Born to Swing|url=https://archive.org/details/borntoswing00wood|date=September 1, 1996|publisher=Sanctuary|isbn=978-1-86074-154-8}}
* {{cite book | first1=William H. | last1=Young | first2=Nancy K. | last2=Young | url=https://books.google.com/books?id=VBljswTLaIEC | title=The Great Depression in America: A Cultural Encyclopedia, Volume 2 | publisher=Greenwood Publishing Group | year=2007 | isbn=978-0-313-33522-8 | access-date=August 28, 2017 | archive-date=October 22, 2016 | archive-url=https://web.archive.org/web/20161022150906/https://books.google.com/books?id=VBljswTLaIEC | url-status=live }}
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{{Refend}}

== Further reading ==
* Freedland, Michael (1998). ''All the Way: A Biography of Frank Sinatra''. St. Martin's Press. {{ISBN|978-0-312-19108-5}}
* Kaplan, James (2015). ''Sinatra: The chairman''. New York: Doubleday. {{ISBN|0385535392}}
* Pickard, Roy (1994). ''Frank Sinatra at the Movies''. Hale. {{ISBN|978-0-7090-5105-3}}

== External links ==
{{commons and category}}
* {{Official website}}
* [http://sinatrafamily.com/news/index.php Sinatra family website] {{Webarchive|url=https://web.archive.org/web/20180511112359/https://sinatrafamily.com/news/index.php |date=May 11, 2018 }}
* [http://www.crooner.fr/player/#crooner_sinatra Frank Sinatra webradio]
* {{AllMusic}}
* [https://njhalloffame.org/hall-of-famers/2008-inductees/frank-sinatra/ Biography] at New Jersey Hall of Fame
* {{IMDb name}}
* {{Discogs artist}}
* [https://vault.fbi.gov/Frank%20Sinatra Frank Sinatra] at FBI Records: The Vault
* [http://www.americanradiohistory.com/Archive-Billboard/60s/1965/Billboard%201965-11-20.pdf ''The Sinatra Report'', a special section of Billboard's November 20, 1965, issue – beginning immediately after page 34]
*[https://americanarchive.org/catalog/cpb-aacip-189-14nk9brh Sinatra in Retrospect; No. 1; The Young Sinatra; Parts 1 and 2] WXXI Public Broadcasting [[American Archive of Public Broadcasting]]

{{Frank Sinatra}}
{{Frank Sinatra singles}}
{{Navboxes
|title = [[List of awards and nominations received by Frank Sinatra|Awards for Frank Sinatra]]
|list =
{{AcademyAwardBestSupportingActor 1941–1960}}
{{American Music Award of Merit}}
{{Cecil B. DeMille Award 1952–1975}}
{{GoldenGlobeBestActorMotionPictureMusicalComedy 1950–1960}}
{{GoldenGlobeBestSuppActorMotionPicture 1943–1960}}
{{Grammy Award for Album of the Year 1960s}}
{{Grammy Award for Record of the Year 1960s}}
{{Grammy Award for Best Male Pop Vocal Performance}}
{{Grammy Legend Award}}
{{Grammy Lifetime Achievement Award}}
{{Jean Hersholt Humanitarian Award}}
{{Kennedy Center Honorees 1980s}}
{{ScreenActorsGuildAward LifeAchievement 1960–1979}}
}}
{{Rat Pack}}
{{Nancy Sinatra}}
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{{DEFAULTSORT:Sinatra, Frank}}
[[Category:Frank Sinatra| ]]
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