Sinatra attempted to pursue an acting career in Hollywood in the early 1940s. While films appealed to him, being exceptionally self-confident, he was rarely enthusiastic towards his own acting, once remarking that "pictures stink". Sinatra made his film debut in 1941, performing in an uncredited sequence in Las Vegas Nights, singing "I'll Never Smile Again" with Tommy Dorsey's The Pied Pipers. In 1943 he had a cameo role along with Duke Ellington and Count Basie in Charles Barton's Reveille with Beverly, making a brief appearance singing "Night and Day". The following year he was given his leading roles in Higher and Higher and Step Lively for RKO Pictures.  In 1945, Metro-Goldwyn-Mayer cast Sinatra opposite Gene Kelly and Kathryn Grayson in the Technicolor musical Anchors Aweigh, in which he played a sailor on leave in Hollywood for four days. A major success, 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. In 1946, Sinatra briefly appeared at the end of Richard Whorf's commercially successful Till the Clouds Roll By, a Technicolor musical biopic of Jerome Kern, in which he sang "Ol' Man River.  In 1949, Sinatra co-starred with Gene Kelly in the Technicolor musical Take Me Out to the Ball Game, a film set in 1908, in which Sinatra and Kelly play baseball players who are part-time vaudevillians. He teamed up with Kelly for a third time in On the Town, playing a sailor on leave in New York City. Today the film is rated very highly by critics, and in 2006 it ranked No. 19 on the American Film Institute's list of best musicals. Both Double Dynamite (1951), an RKO Irving Cummings comedy produced by Howard Hughes, and Joseph Pevney's Meet Danny Wilson (1952) failed to make an impression. The New York World Telegram and Sun ran the headline "Gone on Frankie in '42; Gone in '52".  Fred Zinnemann's From Here to Eternity 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. Sinatra had long been desperate to find a film role which 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. During production, Montgomery Clift became a close friend, and Sinatra later professed that he "learned more about acting from him than anybody I ever knew before". 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. His performance also won a Golden Globe Award for Best Supporting Actor - Motion Picture. 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".  In 1954 Sinatra starred opposite Doris Day in the musical film Young at Heart, and earned critical praise for his performance as a psychopathic killer posing as an FBI agent opposite Sterling Hayden in the film noir Suddenly.  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). After roles in Guys and Dolls, and The Tender Trap, Sinatra was nominated for a BAFTA Award for Best Actor in a Leading Role for his role as hospital orderly in Stanley Kramer's debut picture, Not as a Stranger. During production, Sinatra got drunk with Robert Mitchum and Broderick Crawford and trashed Kramer's dressing room. Kramer vowed to never hire Sinatra again at the time, and later regretted casting him as a Spanish guerrilla leader in The Pride and the Passion (1957).  In 1956 Sinatra featured alongside Bing Crosby and Grace Kelly in High Society for MGM, earning a reported $250,000 for the picture. The public rushed to the cinemas to see Sinatra and Crosby together on-screen, and it ended up earning over $13 million at the box office, becoming one of the highest-grossing pictures of 1956. In 1957, Sinatra starred opposite Rita Hayworth and Kim Novak in George Sidney's Pal Joey, for which he won for the Golden Globe Award for Best Actor - Motion Picture Musical or Comedy. Santopietro considers the scene in which Sinatra sings "The Lady Is a Tramp" to Hayworth to have been the finest moment of his film career. He next portrayed comedian Joe E. Lewis in The Joker Is Wild; the song "All the Way" won the Academy Award for Best Original Song. By 1958 Sinatra was one of the ten biggest box office draws in the United States, appearing with Dean Martin and Shirley MacLaine in Vincente Minnelli's Some Came Running and Kings Go Forth with Tony Curtis and Natalie Wood. "High Hopes", sung by Sinatra in the Frank Capra comedy, A Hole in the Head (1959), won the Academy Award for Best Original Song, and became a chart hit, lasting on the Hot 100 for 17 weeks.  Due to an obligation he owed to 20th Century Fox for walking off the set of Henry King's Carousel (1956), in 1960 Sinatra starred opposite Shirley MacLaine, Maurice Chevalier and Louis Jourdan in Can-Can. He earned $200,000 and 25% of the profits for the performance. Later that year he starred in the Las Vegas-set Ocean's 11, the first film to feature the Rat Pack together and the start of a "new era of screen cool" for Santopietro. Sinatra personally financed the film, and paid Martin and Davis Jr. fees of $150,000 and $125,000 respectively, sums considered exorbitant for the period. In 1962, Sinatra had a leading role opposite Laurence Harvey in The Manchurian Candidate, which he considered to be the role he was most excited about and the high point of his film career. 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." He appeared with the Rat Pack in the western Sergeants 3, following it with 4 for Texas in 1963. For his performance in Come Blow Your Horn, he was nominated for the Golden Globe Award for Best Actor - Motion Picture Musical or Comedy.  Though 1965's Von Ryan's Express was a major success, and he had directed None but the Brave that year, in the mid 1960s, Brad Dexter wanted to "breathe new life" in Sinatra's film career by helping him display the same professional pride in his films as he did his recordings. On one occasion, he gave Sinatra Anthony Burgess's novel A Clockwork Orange (1962) to read, with the idea of making a film, but Sinatra thought it had no potential and did not understand a word.  In the late 1960s, Sinatra became known for playing detectives, including Tony Rome in Tony Rome (1967) and its sequel Lady In Cement (1968). He also played a similar role in 1968's The Detective.  In 1970, Sinatra starred opposite George Kennedy in the western Dirty Dingus Magee, an "abysmal" affair according to Santopietro, which was panned by the critics. The following year, Sinatra received a Golden Globe Cecil B. DeMille Award and had intended to play Detective Harry Callahan in Dirty Harry (1971), but had to turn the role down due to developing Dupuytren's contracture in his hand. 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.

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