Gold Derby
Top 22 movies starring the most Oscar winners
By Matthew Stewart
November 1, 2023
The eclectic entries on this list cover a staggering eight decades of film history, having all been released between 1939 and 2019. Collectively, they themselves won 22 Oscars from 73 nominations, with standouts including respective 1940 and 1957 Best Picture winners “Gone with the Wind” and “Around the World in 80 Days.” The only directors with multiple films on the list are George Marshall (“Variety Girl” and “How the West Was Won”) and Robert Altman (“The Player” and “Prêt-à-Porter”), while the much larger roster of actors who make repeat appearances includes Frank Sinatra, Sophia Loren, John Wayne, Cher, Sean Connery, and Julia Roberts, to name a few.
Every film in this gallery includes at least half a dozen competitive acting Oscar victors in its cast, meaning that honorary wins and those in other categories (such as writing and directing) were not counted. Appearances through archive footage were also not considered, but we did count uncredited performances, self-portrayals within narratives, and voice-only work. It also made no difference whether the listed cast members had already won their Oscars by the time their films were released or if they would go on to achieve their victories later.
1. ‘The Player’ (1992) – 12 winners
Plot: A Hollywood executive overreacts after receiving death threats from a disgruntled screenwriter.
Oscar nominations:
Best Director (Robert Altman)
Best Adapted Screenplay
Best Film Editing
Oscar winners in cast:
– Jack Lemmon (Best Supporting Actor, “Mister Roberts,” 1956; Best Actor, “Save the Tiger,” 1974)
– Rod Steiger (Best Actor, “In the Heat of the Night,” 1968)
– Joel Grey (Best Supporting Actor, “Cabaret,” 1973)
– Louise Fletcher (Best Actress, “One Flew Over the Cuckoo’s Nest,” 1976)
– Anjelica Huston (Best Supporting Actress, “Prizzi’s Honor,” 1986)
– Marlee Matlin (Best Actress, “Children of a Lesser God,” 1987)
– Cher (Best Actress, “Moonstruck,” 1988)
– Whoopi Goldberg (Best Supporting Actress, “Ghost,” 1991)
– Susan Sarandon (Best Actress, “Dead Man Walking,” 1996)
– James Coburn (Best Supporting Actor, “Affliction,” 1999)
– Julia Roberts (Best Actress, “Erin Brockovich,” 2001)
– Tim Robbins (Best Supporting Actor, “Mystic River,” 2004)
Additional Oscar nominees in cast:
Peter Falk, Elliott Gould, Karen Black, Sally Kellerman, Lily Tomlin, Gary Busey, Teri Garr, Sally Kirkland, Dean Stockwell, Nick Nolte, Burt Reynolds, and Richard E. Grant
2. ‘Around the World in 80 Days’ (1956) – 8 winners
Plot: An adaptation of Jules Verne’s 1872 epic novel in which an Englishman wagers that he can circumnavigate the globe in less than three months.
Oscar nominations:
Best Picture – WON
Best Director (Michael Anderson)
Best Adapted Screenplay – WON
Best Color Art Direction
Best Color Cinematography – WON
Best Color Costume Design
Best Film Editing – WON
Best Score – WON
Oscar winners in cast:
– Victor McLaglen (Best Actor, “The Informer,” 1936)
– Charles Coburn (Best Supporting Actor, “The More the Merrier,” 1944)
– Ronald Colman (Best Actor, “A Double Life,” 1948)
– Frank Sinatra (Best Supporting Actor, “From Here to Eternity,” 1954)
– David Niven (Best Actor, “Separate Tables,” 1959)
– John Mills (Best Supporting Actor, “Ryan’s Daughter,” 1971)
– John Gielgud (Best Supporting Actor, “Arthur,” 1982)
– Shirley MacLaine (Best Actress, “Terms of Endearment,” 1984)
Additional Oscar nominees in cast:
Charles Boyer, Robert Morley, Jack Oakie, Trevor Howard, and Glynis Johns
3, The Greatest Story Ever Told (1965) – 8 winners
Plot: A biopic covering the entire three-decade lifespan of Jesus of Nazareth.
Oscar nominations:
Best Color Art Direction
Best Color Cinematography
Best Color Costume Design
Best Original Score
Best Visual Effects
Oscar winners in cast:
– Joseph Schildkraut (Best Supporting Actor, “The Life of Emile Zola,” 1938)
– Van Heflin (Best Supporting Actor, “Johnny Eager,” 1943)
– Jose Ferrer (Best Actor, “Cyrano de Bergerac,” 1951)
– Charlton Heston (Best Actor, “Ben-Hur,” 1960)
– Shelley Winters (Best Supporting Actress, “The Diary of Anne Frank,” 1960 / “A Patch of Blue,” 1966)
– Sidney Poitier (Best Actor, “Lilies of the Field,” 1964)
– John Wayne (Best Actor, “True Grit,” 1970)
– Martin Landau (Best Supporting Actor, “Ed Wood,” 1995)
Additional Oscar nominees in cast:
Claude Rains, Angela Lansbury, Dorothy McGuire, Sal Mineo, Carroll Baker, Ed Wynn, Victor Buono, Telly Savalas, Robert Loggia, and Max von Sydow
4.‘Hamlet’ (1996) – 8 winners
Plot: The titular Shakespearean prince has an existential crisis following his uncle’s murder and usurpation of his father, the King of Denmark
Oscar nominations:
Best Adapted Screenplay
Best Art Direction
Best Costume Design
Best Original Dramatic Score
Oscar winners in cast:
– Jack Lemmon (Best Supporting Actor, “Mister Roberts,” 1956; Best Actor, “Save the Tiger,” 1974)
– Charlton Heston (Best Actor, “Ben-Hur,” 1960)
– Julie Christie (Best Actress, “Darling,” 1966)
– John Mills (Best Supporting Actor, “Ryan’s Daughter,” 1971)
– John Gielgud (Best Supporting Actor, “Arthur,” 1982)
– Robin Williams (Best Supporting Actor, “Good Will Hunting,” 1998)
– Judi Dench (Best Supporting Actress, “Shakespeare in Love,” 1999)
– Kate Winslet (Best Actress, “The Reader,” 2009)
Additional Oscar nominees in cast:
Kenneth Branagh, Gérard Depardieu, and Rosemary Harris
5. ‘How the West Was Won’ (1962) – 7 winners
Plot: Over a span of 50 years, families and individuals live through the various hardships that afflicted 19th century American westerners.
Oscar nominations:
Best Picture
Best Original Screenplay – WON
Best Color Art Direction
Best Color Cinematography
Best Color Costume Design
Best Film Editing – WON
Best Original Score
Best Sound – WON
Oscar winners in cast:
– Walter Brennan (Best Supporting Actor, “Come and Get It,” 1937 / “Kentucky,” 1939 / “The Westerner,” 1941)
– Spencer Tracy (Best Actor, “Captains Courageous,” 1938 / “Boys Town,” 1939)
– James Stewart (Best Actor, “The Philadelphia Story,” 1941)
– Karl Malden (Best Supporting Actor, “A Streetcar Named Desire,” 1952)
– Gregory Peck (Best Actor, “To Kill a Mockingbird,” 1963)
– John Wayne (Best Actor, “True Grit,” 1970)
– Henry Fonda (Best Actor, “On Golden Pond,” 1982)
Additional Oscar nominees in cast:
Raymond Massey, Agnes Moorehead, Richard Widmark, Thelma Ritter, Lee J. Cobb, Carroll Baker, Russ Tamblyn, Carolyn Jones, Debbie Reynolds, and Robert Preston
‘The Oscar’ (1966) – 7 winners
Plot: A fictional actor’s unscrupulous career choices are examined as he awaits the result of his first Oscar nomination.
6, ‘The Oscar’ (1966) – 7 winners
Plot: A fictional actor’s unscrupulous career choices are examined as he awaits the result of his first Oscar nomination.
Oscar nominations:
Best Color Art Direction
Best Color Costume Design
Oscar winners in cast:
– Walter Brennan (Best Supporting Actor, “Come and Get It,” 1937 / “Kentucky,” 1939 / “The Westerner,” 1941)
– Joan Crawford (Best Actress, “Mildred Pierce,” 1946)
– James Dunn (Best Supporting Actor, “A Tree Grows in Brooklyn,” 1946)
– Broderick Crawford (Best Actor, “All the King’s Men,” 1950)
– Frank Sinatra (Best Supporting Actor, “From Here to Eternity,” 1954)
– Ernest Borgnine (Best Actor, “Marty,” 1956)
– Ed Begley (Best Supporting Actor, “Sweet Bird of Youth,” 1963)
Additional Oscar nominees in cast:
Merle Oberon and Eleanor Parker
7. ‘The Swarm’ (1978) – 7 winners
Plot: America is terrorized by a gigantic swarm of deadly African bees.
Oscar nomination:
Best Costume Design
Oscar winners in cast:
– Olivia de Havilland (Best Actress, “To Each His Own,” 1947 / “The Heiress,” 1950)
– Jose Ferrer (Best Actor, “Cyrano de Bergerac,” 1951)
– Patty Duke (Best Supporting Actress, “The Miracle Worker,” 1963)
– Ben Johnson (Best Supporting Actor, “The Last Picture Show,” 1972)
– Lee Grant (Best Supporting Actress, “Shampoo,” 1976)
– Henry Fonda (Best Actor, “On Golden Pond,” 1982)
– Michael Caine (Best Supporting Actor, “Hannah and Her Sisters,” 1987 / “The Cider House Rules,” 2000)
Additional Oscar nominees in cast:
Richard Widmark and Katharine Ross
8. ‘Prêt-à-Porter’ (1994) – 7 winners
Plot: A vast array of artists and journalists interact during Paris Fashion Week.
Oscar nominations:
None
Oscar winners in cast:
– Sophia Loren (Best Actress, “Two Women,” 1962)
– Linda Hunt (Best Supporting Actress, “The Year of Living Dangerously,” 1984)
– Cher (Best Actress, “Moonstruck,” 1988)
– Kim Basinger (Best Supporting Actress, “L.A. Confidential,” 1998)
– Julia Roberts (Best Actress, “Erin Brockovich,” 2001)
– Tim Robbins (Best Supporting Actor, “Mystic River,” 2004)
– Forest Whitaker (Best Actor, “The Last King of Scotland,” 2007)
Additional Oscar nominees in cast:
Marcello Mastroianni, Anouk Aimée, Sally Kellerman, Teri Garr, Danny Aiello, Stephen Rea, Lauren Bacall, and Richard E. Grant
9. ‘The Help’ (2011) – 7 winners
Plot: In the 1960s, a young, white writer anonymously releases a book of her interviews with Black maids
Oscar nominations:
Best Picture
Best Actress (Viola Davis)
Best Supporting Actress (Octavia Spencer – WON; Jessica Chastain)
Oscar winners in cast:
– Sissy Spacek (Best Actress, “Coal Miner’s Daughter,” 1981)
– Mary Steenburgen (Best Supporting Actress, “Melvin and Howard,” 1981)
– Octavia Spencer (Best Supporting Actress, “The Help,” 2012)
– Emma Stone (Best Actress, “La La Land,” 2017)
– Viola Davis (Best Supporting Actress, “Fences,” 2017)
– Allison Janney (Best Supporting Actress, “I, Tonya,” 2018)
– Jessica Chastain (Best Actress, “The Eyes of Tammy Faye,” 2022)
Additional Oscar nominees in cast:
Cicely Tyson and Aunjanue Ellis
10. ‘Avengers: Endgame’ (2019) – 7 winners
Plot: The conclusion of the Marvel Cinematic Universe’s 11-year Infinity Saga in which the titular heroes assemble to defeat their most powerful enemy.
Oscar nomination:
Best Visual Effects
Oscar winners in cast:
– William Hurt (Best Actor, “Kiss of the Spider Woman,” 1986)
– Michael Douglas (Best Actor, “Wall Street,” 1988)
– Marisa Tomei (Best Supporting Actress, “My Cousin Vinny,” 1993)
– Gwyneth Paltrow (Best Actress, “Shakespeare in Love,” 1999)
– Tilda Swinton (Best Supporting Actress, “Michael Clayton,” 2008)
– Natalie Portman (Best Actress, “Black Swan,” 2011)
– Brie Larson (Best Actress, “Room,” 2016)
Additional Oscar nominees in cast:
Robert Redford, Michelle Pfeiffer, Robert Downey Jr., Angela Bassett, Samuel L. Jackson, Don Cheadle, Josh Brolin, Jeremy Renner, Mark Ruffalo, Bradley Cooper, Benedict Cumberbatch, Scarlett Johansson, Chadwick Boseman, and Kerry Condon
11. ‘Gone with the Wind’ (1939) – 6 winners
Plot: A southern belle’s charmed life changes drastically once the American Civil War begins.
Oscar nominations:
Best Picture – WON
Best Director (Victor Fleming) – WON
Best Screenplay – WON
Best Actor (Clark Gable)
Best Actress (Vivien Leigh) – WON
Best Supporting Actress (Hattie McDaniel – WON; Olivia de Havilland)
Best Art Direction – WON
Best Color Cinematography – WON
Best Film Editing – WON
Best Original Score
Best Sound Recording
Best Special Effects
Oscar winners in cast:
– Clark Gable (Best Actor, “It Happened One Night,” 1935)
– Vivien Leigh (Best Actress, “Gone with the Wind,” 1940)
– Thomas Mitchell (Best Supporting Actor, “Stagecoach,” 1940)
– Hattie McDaniel (Best Supporting Actress, “Gone with the Wind,” 1940)
– Jane Darwell (Best Supporting Actress, “The Grapes of Wrath,” 1941)
– Olivia de Havilland (Best Actress, “To Each His Own,” 1947 / “The Heiress,” 1950)
Additional Oscar nominees in cast:
Leslie Howard, Barbara O’Neil, and Richard Farnsworth
12. Variety Girl’ (1947) – 6 winners
Plot: Two aspiring actresses encounter dozens of contract players while at the Paramount studio.
Oscar nominations:
None
Oscar winners in cast:
– Gary Cooper (Best Actor, “Sergeant York,” 1942 / “High Noon,” 1953)
– Bing Crosby (Best Actor, “Going My Way,” 1945)
– Barry Fitzgerald (Best Supporting Actor, “Going My Way,” 1945)
– Ray Milland (Best Actor, “The Lost Weekend,” 1946)
– William Holden (Best Actor, “Stalag 17,” 1954)
– Burt Lancaster (Best Actor, “Elmer Gantry,” 1961)
Additional Oscar nominees in cast:
Barbara Stanwyck, William Bendix, Paulette Goddard, William Demarest, Cecil Kellaway, and Robert Preston
13. ‘The Longest Day’ (1962) – 6 winners
Plot: A dramatization of the 1944 Normandy landings which led to the liberation of the Western European countries under Axis occupation.
Oscar nominations:
Best Picture
Best Black-and-White Art Direction
Best Black-and-White Cinematography – WON
Best Film Editing
Best Special Effects – WON
Oscar winners in cast:
– Edmond O’Brien (Best Supporting Actor, “The Barefoot Contessa,” 1955)
– Red Buttons (Best Supporting Actor, “Sayonara,” 1958)
– Rod Steiger (Best Actor, “In the Heat of the Night,” 1968)
– John Wayne (Best Actor, “True Grit,” 1970)
– Henry Fonda (Best Actor, “On Golden Pond,” 1982)
– Sean Connery (Best Supporting Actor, “The Untouchables,” 1988)
Additional Oscar nominees in cast:
Alexander Knox, Robert Mitchum, Robert Ryan, Richard Todd, Richard Burton, Eddie Albert, Sal Mineo, Stuart Whitman, Frank Finlay, and George Segal
14. ‘Murder on the Orient Express’ (1974) – 6 winners
Plot: In 1935, Detective Hercule Poirot unexpectedly finds himself solving a murder while stuck on a snow-stalled train.
Oscar nominations:
Best Adapted Screenplay
Best Actor (Albert Finney)
Best Supporting Actress (Ingrid Bergman) – WON
Best Cinematography
Best Costume Design
Best Original Dramatic Score
Oscar winners in cast:
– Ingrid Bergman (Best Actress, “Gaslight,” 1945 / “Anastasia,” 1957; Best Supporting Actress, “Murder on the Orient Express,” 1975)
– Wendy Hiller (Best Supporting Actress, “Separate Tables,” 1959)
– Martin Balsam (Best Supporting Actor, “A Thousand Clowns,” 1966)
– Vanessa Redgrave (Best Supporting Actress, “Julia,” 1978)
– John Gielgud (Best Supporting Actor, “Arthur,” 1982)
– Sean Connery (Best Supporting Actor, “The Untouchables,” 1988)
Additional Oscar nominees in cast:
Richard Widmark, Anthony Perkins, Albert Finney, Rachel Roberts, and Lauren Bacall
15. A Bridge Too Far (1977) – 6 winners
Plot: In September 1944, the Allied military coalition attempted to carry out Operation Market Garden
Oscar nominations:
None
Oscar winners in cast:
– Laurence Olivier (Best Actor, “Hamlet,” 1949)
– Maximilian Schell (Best Actor, “Judgment at Nuremberg,” 1962)
– Gene Hackman (Best Actor, “The French Connection,” 1972; Best Supporting Actor, “Unforgiven,” 1993)
– Michael Caine (Best Supporting Actor, “Hannah and Her Sisters,” 1987 / “The Cider House Rules,” 2000)
– Sean Connery (Best Supporting Actor, “The Untouchables,” 1988)
– Anthony Hopkins (Best Actor, “The Silence of the Lambs,” 1992 / “The Father,” 2021)
Additional Oscar nominees in cast:
Elliott Gould, Ryan O’Neal, Liv Ullmann, James Caan, Robert Redford, and Denholm Elliott
16. ‘JFK’ (1991) – 6 winners
Plot: A few years after the assassination of President John F. Kennedy, District Attorney Jim Garrison works to bring the culprits to justice.
Oscar nominations:
Best Picture
Best Director (Oliver Stone)
Best Adapted Screenplay
Best Supporting Actor (Tommy Lee Jones)
Best Cinematography – WON
Best Film Editing – WON
Best Original Score
Best Sound
Oscar winners in cast:
– Jack Lemmon (Best Supporting Actor, “Mister Roberts,” 1956; Best Actor, “Save the Tiger,” 1974)
– Walter Matthau (Best Supporting Actor, “The Fortune Cookie,” 1967)
– Sissy Spacek (Best Actress, “Coal Miner’s Daughter,” 1981)
– Joe Pesci (Best Supporting Actor, “Goodfellas,” 1991)
– Tommy Lee Jones (Best Supporting Actor, “The Fugitive,” 1994)
– Gary Oldman (Best Actor, “Darkest Hour,” 2018)
Additional Oscar nominees in cast:
Sally Kirkland, Kevin Costner, and Laurie Metcalf
17. ‘A Time to Kill’ (1996) – 6 winners
Plot: In Mississippi, a Black man stands trial for killing the two white men who raped his daughter.
Oscar nominations:
None
Oscar winners in cast:
– Brenda Fricker (Best Supporting Actress, “My Left Foot,” 1990)
– Kevin Spacey (Best Supporting Actor, “The Usual Suspects,” 1996; Best Actor, “American Beauty,” 2000)
– Chris Cooper (Best Supporting Actor, “Adaptation,” 2003)
– Sandra Bullock (Best Actress, “The Blind Side,” 2010)
– Octavia Spencer (Best Supporting Actress, “The Help,” 2012)
– Matthew McConaughey (Best Actor, “Dallas Buyers Club,” 2014)
Additional Oscar nominees in the cast:
Samuel L. Jackson
18. ‘The First Wives Club’ (1996) – 6 winners
Plot: Three friends team up to get even with their philandering ex-husbands.
Oscar nomination:
Best Original Comedy/Musical Score
Oscar winners in cast:
– Maggie Smith (Best Actress, “The Prime of Miss Jean Brodie,” 1970; Best Supporting Actress, “California Suite,” 1979)
– Goldie Hawn (Best Supporting Actress, “Cactus Flower,” 1970)
– Eileen Heckart (Best Supporting Actress, “Butterflies Are Free,” 1973)
– Diane Keaton (Best Actress, “Annie Hall,” 1978)
– Marcia Gay Harden (Best Supporting Actress, “Pollock,” 2001)
– J.K. Simmons (Best Supporting Actor, “Whiplash,” 2015)
Additional Oscar nominees in cast:
Bette Midler and Stockard Channing
19. ‘The Good Shepherd’ (2006) – 6 winners
Plot: A fictionalized account of the development of the U.S. Central Intelligence Agency.
Oscar nominations:
Best Art Direction
Oscar winners in cast:
– Robert De Niro (Best Supporting Actor, “The Godfather Part II,” 1975; Best Actor, “Raging Bull,” 1981)
– Timothy Hutton (Best Supporting Actor, “Ordinary People,” 1981)
– William Hurt (Best Actor, “Kiss of the Spider Woman,” 1986)
– Joe Pesci (Best Supporting Actor, “Goodfellas,” 1991)
– Angelina Jolie (Best Supporting Actress, “Girl, Interrupted,” 2000)
– Eddie Redmayne (Best Actor, “The Theory of Everything,” 2015)
Additional Oscar nominees in cast:
Matt Damon and Alec Baldwin
20. ‘Nine’ (2009) – 6 winners
Plot: A creatively stunted Italian filmmaker seeks inspiration from the many women in his life.
Oscar nominations:
Best Supporting Actress (Penélope Cruz)
Best Art Direction
Best Costume Design
Best Original Song (“Take It All”)
Oscar winners in cast:
– Sophia Loren (Best Actress, “Two Women,” 1962)
– Daniel Day-Lewis (Best Actor, “My Left Foot,” 1990 / “There Will Be Blood,” 2008 / “Lincoln,” 2013)
– Judi Dench (Best Supporting Actress, “Shakespeare in Love,” 1999)
– Nicole Kidman (Best Actress, “The Hours,” 2003)
– Marion Cotillard (Best Actress, “La Vie en Rose,” 2008)
– Penélope Cruz (Best Supporting Actress, “Vicky Cristina Barcelona,” 2009)
Additional Oscar nominee in cast:
Kate Hudson
21. ‘I’m Still Here’ (2010) – 6 winners
Plot: A mockumentary chronicling Joaquin Phoenix’s retirement from acting and foray into hip hop music.
Oscar nominations:
None
Oscar winners in cast:
– Jack Nicholson (Best Actor, “One Flew Over the Cuckoo’s Nest,” 1976 / “As Good As It Gets,” 1998; Best Supporting Actor, “Terms of Endearment,” 1984)
– Sean Penn (Best Actor, “Mystic River,” 2004 / “Milk,” 2009)
– Jamie Foxx (Best Actor, “Ray,” 2005)
– Natalie Portman (Best Actress, “Black Swan,” 2011)
– Casey Affleck (Best Actor, “Manchester by the Sea,” 2017)
– Joaquin Phoenix (Best Actor, “Joker,” 2020)
Additional Oscar nominee in cast:
Edward James Olmos
22. ‘The Dark Knight Rises’ (2012) – 6 winners
Plot: The conclusion of Christopher Nolan’s Batman trilogy in which the retired superhero is forced back into action.
Oscar nominations:
None
Oscar winners in cast:
– Michael Caine (Best Supporting Actor, “Hannah and Her Sisters,” 1987 / “The Cider House Rules,” 2000)
– Morgan Freeman (Best Supporting Actor, “Million Dollar Baby,” 2005)
– Marion Cotillard (Best Actress, “La Vie en Rose,” 2008)
– Christian Bale (Best Supporting Actor, “The Fighter,” 2011)
– Anne Hathaway (Best Supporting Actress, “Les Misérables,” 2013)
– Gary Oldman (Best Actor, “Darkest Hour,” 2018)
Additional Oscar nominee in cast:
Tom Hardy
