Entertainment TV & Film 6 Great Movies Starring Frank Sinatra An Oscar and Many Memorable Roles for the Chairman of the Board Share PINTEREST Email Print TV & Film Movies Classic Movies Best Movie Lists Comedies Science Fiction Movies War Movies International Movies Movies For Kids Horror Movies Movie Awards Animated Films TV Shows By Shawn Dwyer Updated November 19, 2017 While best remembered for recording a multitude of hits like "Strangers in the Night," "My Way," and "Summer Wind," Frank Sinatra also forged a successful film career that included starring roles in several classics and an Oscar for Best Supporting Actor Being a best-selling crooner, Sinatra naturally had his start in musicals, but soon displayed considerable acting chops in dramas, action movies, and political thrillers. Here are six classic movies starring Frank Sinatra. 01 of 06 "On the Town" – 1949 Hulton Archive/Archive Photos/Getty Images Though the star of this classic musical was undoubtedly Gene Kelly, Sinatra more than held his own as part of a trio of Navy sailors (Sinatra, Kelly and Jules Munshin) who spend their 24-hour shore leave living it up in New York City. Along the way, they meet three women, an aspiring dancer (Vera-Ellen) hiding her burlesque job, an aggressive cabbie (Betty Garrett) and an anthropology student (Ann Miller), all of which leads to fun, adventure and lots of song-and-dance. As with most musicals,"On the Town" was short on plot and character, but featured a number of exuberant dance numbers. The film was the third and last collaboration between Sinatra and Kelly, and marked the beginning of a brief, but steep downslide in Sinatra’s career. 02 of 06 "From Here to Eternity" – 1953 Directed by Fred Zinnemann and starring Burt Lancaster, "From Here to Eternity" earned Sinatra the Academy Award for Best Supporting Actor – the only Oscar of his career – and announced his comeback following a few years of professional decline. Sinatra delivered a strong performance as Angelo Maggio, a wisecracking army private targeted for persecution by a sadistic sergeant (Ernest Borgnine). Though the main action focused on Lancaster’s court martial of Montgomery Clift and romance with Deborah Kerr, Sinatra was memorable as the ill-fated Maggio. Rumor had it that Sinatra landed the part because of his alleged Mafia connections, which was alluded to years later with the Sinatra-like character Johnny Fontane and his connection to Vito Corleone (Marlon Brando) in Francis Ford Coppola’s "The Godfather "(1972). 03 of 06 "The Man With the Golden Arm" – 1955 Warner Bros. Home Entertainment Stark and gritty even by today’s standards, director Otto Preminger’s addiction drama, "The Man With the Golden Arm," was controversial in its day for dealing so directly with narcotics addiction. But it also was a harrowing account of a man’s struggle to stay clean and without a doubt was Sinatra’s best dramatic performance of his career. The actor played Frankie Machine, an expert card player and heroin addict who is released from prison and becomes determined to maintain a straight and narrow path. However, his greedy invalid wife (Eleanor Parker) – confined to a wheelchair from an accident he caused – pressures him to enter a high-stakes card game, leading to his eventual relapse. She’s faking her condition, of course, and the discovery of this leads to her murdering his drug dealer and making Frankie take the fall. Sinatra spent time at a rehabilitation clinic with addicts going cold turkey with their recoveries, which lent great authenticity to his own harrowing scene where Frankie struggles once again to get clean. Sinatra deservedly received an Oscar nomination for Best Actor, but lost out to Ernest Borgnine’s performance in "Marty." 04 of 06 "Ocean's 11" – 1960 Warner Bros. Back on top once again, Sinatra cemented his reputation as a cool cat with "Ocean’s 11," a lighthearted heist movie that became the definitive Rat Pack movie. Also starring pals Dean Martin, Sammy Davis, Jr., Joey Bishop and Peter Lawford, "Ocean’s 11" featured Sinatra as Danny Ocean, a professional gambler who organizes his army buddies into a crew that attempts to simultaneously rob five Las Vegas casinos at the stroke of midnight on New Year’s Eve. All have their reasons for committing the crime, as Ocean recruits a large enough group to pull the job, only to see their plans literally go up in flames. Never pretending to be anything more than it already is, the film was a perfect vehicle for all involved. Years later it was remade to much greater effect by Steven Soderbergh with George Clooney taking over Sinatra’s role. 05 of 06 "The Manchurian Candidate" – 1962 MGM Home Entertainment A far cry from the ring-a-ding-ding vibe of the Rat Pack, "The Manchurian Candidate" was a tense political thriller that offered Sinatra one of his most challenging roles, and from this perspective ranks as his best film. Sinatra starred as Captain Bennett Marco, a Korean War veteran returned home after being held in captivity by Korean troops. One member of his unit, Sgt. Raymond Shaw (Laurence Harvey), returns a war hero, but almost from the start, there seems to be something wrong with both him and the other members of his unit. Plagued by nightmares, Marco comes to learn that he and his unit were brainwashed by the Chinese during their confinement and that Shaw has been turned into a mindless killer whose overly aggressive mother (Angela Lansbury) helps plot the assassination of her soon-to-be vice presidential husband (James Gregory). Fueled by Cold War paranoia, "The Manchurian Candidate" was a nail-biting thriller that featured extraordinary performances from the entire cast. 06 of 06 "Von Ryan's Express" – 1965 20th Century Fox An intense thrill ride set during World War II, "Von Ryan’s Express" sidestepped the historical backdrop of most war movies in favor of non-stop action, while marking the beginning of the end of Sinatra’s film career. Sinatra played Col. Joseph L. Ryan, a U.S. pilot who uses his grit and determination to lead a prisoner of war escape that requires the hijacking of a German train speeding across Italy to Switzerland. Sinatra made for a convincing action hero, while co-star Trevor Howard provided necessary internal conflict as a curmudgeonly British officer. "Von Ryan’s Express" featured great cinematography and special effects that were ahead of its time. But the picture also proved to be one of the last good movies of Sinatra’s career, as he slipped into retirement for the first time just a few years later.