Editing Frank Sinatra (section)

=== 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}}