Ten Best Frank Sinatra Hollywood Movies

Lobby card: Frank Sinatra and Kim Novak in The Man with the Golden Arm (1955)

Frank Sinatra was born Francis Albert Sinatra in Hoboken, New Jersey, on December 12, 1915. Sinatra made his motion picture debut in Las Vegas Nights (1941), appearing as a singer in the Tommy Dorsey Orchestra. Frank Sinatra – a.k.a. “Ol’ Blue Eyes,” “The Voice,” “The Chairman of the Board,” et al., – died in Los Angeles, California, on May 14, 1998.

Here are ten Frank Sinatra movies that no film fan should ever miss. We begin in 1955…

The Man with the Golden Arm (United Artists, 1955)

Frank Sinatra plays Frankie Machine, an ex-con who emerges from prison free of his heroin addiction. The card dealer is hoping to hook on with a band as a drummer, but the old smack demons are never far away, led by neighborhood drug peddler Louie Fomorowski (Darren McGavin). The scene in which Sinatra’s Machine goes cold turkey, trying to end his heroin dependency in Molly’s (Kim Novak) apartment is one of the best performances of his career. Based on the novel by Nelson Algren, the gritty The Man with the Golden Arm also features Eleanor Parker, Arnold Stang and Robert Strauss. The movie earned three Oscar nominations.

Academy Award nomination: Best Actor

Great Sinatra line (to Kim Novak’s Molly): “You mean just stop? Cold turkey? You don’t understand! The pain…”

Director: Otto Preminger

On DVD: The Man with the Golden Arm 50th Anniversary Edition (Hart Sharp, 2005)

Ocean’s Eleven (Warner Bros., 1960)

Frank Sinatra plays Danny Ocean, the leader of a gang of ex-82nd Airborne paratroopers who carry out a daring heist of five Las Vegas casinos on New Year’s Eve. This is Sinatra and the Rat Pack at its very best, with Dean Martin, Sammy Davis Jr., Peter Lawford and Joey Bishop all present and accounted for in Sin City. Add to that the talents of Angie Dickinson, Cesar Romero and Richard Conte – along with cameo appearances by Red Skelton and Shirley MacLaine as an inebriated, mink-clad floozy – and Ocean’s Eleven is the stuff of Hollywood history. Ain’t that a kick in the head?

Great Sinatra line (on carrying out the heist): “Why waste those cute little tricks that the Army taught us just because it’s sort of peaceful now.”

Director: Lewis Milestone

On DVD: Ocean’s Eleven (Warner, 2008)

French petite movie poster: Frank Sinatra in Ocean’s Eleven (1960)

Von Ryan’s Express (Twentieth Century-Fox, 1965)

Frank Sinatra plays Colonel Joseph Ryan, an American POW who leads over 600 Allied prisoners in a desperate run to freedom from German forces in 1943 Italy. The role is tailor-made for Ol’ Blue Eyes, who must win the support of hostile British soldiers in order to successfully execute his plan. Trevor Howard, Raffaella Carra, Brad Dexter, Edward Mulhare, Wolfgang Preiss and James Brolin join Sinatra in the cast. The train sequence is one of the most thrilling in Hollywood escapist history, with Sinatra leading the charge.

Great Sinatra line (after Brad Dexter’s Sgt. Bostick remarks that they now have a bird-colonel in camp): “A bird-colonel outranks a bird-brain, clear?”

Director: Mark Robson

On DVD: Von Ryan’s Express Two-Disc Collector’s Edition (20th Century-Fox, 2007)

From Here to Eternity (Columbia, 1953)

Frank Sinatra appears as Private Angelo Maggio in the big screen adaptation of the classic James Jones novel. Sinatra, who actively campaigned for the role of Maggio, plays a tragic figure, an enlisted man who is beaten to death by Sgt. Fatso Judson (Ernest Borgnine), the sadistic keeper of the local Army stockade. From Here to Eternity, set in Hawaii in the months preceding the Japanese attack at Pearl Harbor on December 7, 1941, earned 13 Academy Award nominations, bringing home eight Oscars, including Best Picture, Best Director, Best Screenplay and Best Supporting Actress (Donna Reed). Burt Lancaster, Montgomery Clift and Deborah Kerr star.

Academy award nomination: Best Supporting Actor (won)

Great Sinatra line: “Only my friends can call me a little wop!”

Director: Fred Zinnemann

On DVD: From Here to Eternity (Columbia TriStar, 2001)

Anchors Aweigh (MGM, 1945)

Frank Sinatra plays Clarence Doolittle opposite Gene Kelly’s Joseph Brady in this lively World War II musical. The two are sailors stationed aboard an aircraft carrier that docks in Los Angeles, where they embark on four days’ leave. Sinatra portrays the naive kid from Brooklyn while Kelly is the old hand with the ladies. There’s plenty of singing and dancing in this one, with Variety commenting: “Anchors Aweigh is solid musical fair. The production numbers are zingy; the songs are extremely listenable; the color treatment outstanding.” It was the veteran dancer Gene Kelly who whipped Sinatra in shape for the film, telling his pupil after eight weeks of grueling instruction: “Francis, you’ve worked your way up from lousy to adequate – I’m ready to dance on camera with you.” Anchors Aweigh garnered five Academy Award nominations, with George Stoll bringing home the lone Oscar for Best Scoring of a Musical Picture.

Great Sinatra line (singing): “I fall in love too easily, I fall in love too fast.”

Director: George Sidney

On DVD: Anchors Aweigh (Warner, 2008)

Promotional movie still: Frank Sinatra and Gene Kelly in Anchors Aweigh (1945)

Meet Danny Wilson (Universal, 1952)

Frank Sinatra stars as the title character, a fledgling singer and pool hustler waiting for his big break in show business. Danny and partner Mike Ryan (Alex Nicol) meet mobster Nick Driscoll a.k.a. Joe Martell (Raymond Burr), who hires Danny to sing at his nightclub, collecting half of Danny’s future income. Sinatra performs such gems as “All of Me,” “I’ve Got a Crush on You,” “That Old Black Magic,” and “How Deep Is the Ocean?” A slim Shelley Winters plays Joy Carroll, Danny’s love interest. It was reported that Sinatra and Winters fought throughout the production.

Great Sinatra line (singing): “That old black magic has me in its spell, that old black magic that you weave so well. Those icy fingers up and down my spine, That same old witchcraft when your eyes meet mine.”

Director: Joseph Pevney

On DVD: Not commercially available

The Joker Is Wild (Paramount, 1957)

Frank Sinatra plays real-life comic Joe E. Lewis (1902-1971), charting his rise as a promising singer in the 1920s. But a vicious knife attack and beating by one of Al Capone’s top lieutenants in 1927 severely injures his voice, ruining his career as a singer. But after learning to speak again, Lewis becomes a top-notch comedian, only to fall from grace in a losing battle with the bottle. Sinatra and Lewis were long-time friends, with Lewis later signing a contract in 1961 to record the comic album, “It Is Now Post Time,” for Sinatra’s Reprise label. Jimmy Van Heusen and Sammy Cahn won an Oscar for Best Original Song, “All the Way.” Mitzi Gaynor, Jeanne Crain, Eddie Albert and Jackie Coogan also appear.

Great Sinatra line (doing a comic routine): “You’re not drunk enough if you can still lie on the floor without hanging on.”

Director: Charles Vidor

On DVD: Not commercially available

Italian movie poster: Frank Sinatra in The Joker Is Wild (1957)

The Manchurian Candidate (United Artists, 1962)

Frank Sinatra plays Bennett Marco, a U.S. Army officer who with his platoon is captured during the Korean War and brainwashed by Chinese Communists. Marco’s nightmares later lead to an investigation which uncovers a “sleeper” assassin among the returning POWs in the person of Raymond Shaw (Laurence Harvey). Based on the novel by Richard Condon, The Manchurian Candidate is a wild political thriller, with Janet Leigh and Angela Lansbury also in top form. The movie garnered two Oscar nominations for Best Supporting Actress (Lansbury) and Best Film Editing.

Great Sinatra line: “I’ve been having this nightmare. A real swinger of a nightmare, too.”

Director: John Frankenheimer

On DVD: The Manchurian Candidate Special Edition (MGM, 2004)

Pal Joey (Columbia, 1957)

Frank Sinatra stars as Joey Evans, a charming skirt-chaser who lands a gig at The Barbary Coast nightclub in San Francisco. Evans becomes the third spoke in a love triangle comprised of Linda English (Kim Novak) and Vera Simpson (Rita Hayworth). There are plenty of Sinatra tunes in this musical, including “There’s a Small Hotel,” “The Lady Is a Tramp,” “Bewitched” and “I Didn’t Know What Time It Was.” Pal Joey earned four Oscar nominations.

Great Sinatra line: “The only thing I’m superstitious about is thirteen in a bed.”

Director: George Sidney

On DVD: Pal Joey (Columbia TriStar, 1999)

The Naked Runner (Warner Bros., 1967)

Frank Sinatra plays Sam Laker, an American businessman and former OSS operative working in London who is recruited by British Intelligence to deliver an important message inside East Germany. The plan goes awry when Laker’s 14-year-old son Patrick (Michael Newport) is kidnapped by East German agents, who want Laker to carry out an assassination in Copenhagen in exchange for the boy’s release. The sleeper in Frank Sinatra’s movie career, The Naked Runner is a taut, intricate suspense thriller with a decidedly European flavor of filmmaking. Sinatra was paid $1 million and box-office participation for his services.

Great Sinatra line (on the kidnapping of his son): “Patrick!”

Director: Sidney J. Furie

On DVD: Not commercially available

Lobby card: Frank Sinatra in The Naked Runner (1967)

Ten More Frank Sinatra Film Favorites

  • Some Came Running (1958)
  • Robin and the 7 Hoods (1964)
  • Assault on a Queen (1966)
  • Guys and Dolls (1955)
  • On the Town (1949)
  • Young at Heart (1954)
  • Suddenly (1954)
  • A Hole in the Head (1959)
  • Come Blow Your Horn (1963)
  • Tony Rome (1967)

Australian one sheet movie poster: Frank Sinatra in Tony Rome (1967)

Images Credit

  • All images courtesy Heritage Auction Galleries, Dallas, Texas