Editing Frank Sinatra (section)

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

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

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

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

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

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

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

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

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

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

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