Editing Frank Sinatra (section)

== 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>