Movies featuring the most former Oscar Winners

According to Wikipedia, Beau Geste is the only movie that features as many as four Academy Award winners for Best Actor
in a Leading Role (Gary Cooper, Ray Milland, Susan Hayward, Broderick Crawford) prior to any of the actors receiving the Best Actor Award.

Fast Times at Ridgemont High has three (Nicholas Cage, Forrest Whitaker, and Sean Penn).

What movie features the **most **Academy Award Winners who had received their Oscar(s) before the film was made?

So far, I’m thinking Grumpier Old Men (Jack Lemmon, Walter Matthau, and Sophia Loren) and Steel Magnolias (Sally Field, Shirley McLaine, and Olympia Dukakis) are the winners…Do I hear four?

I thought I had it, but A Bridge Too Far (1977) also only has three:
Gene Hackman (1972), Maximilian Schell (1962) and Laurence Olivier (1949).

But it also had Sean Connery (1988), Michael Caine (1986,1999), Anthony Hopkins (1992), Robert Redford (1981) and Richard Attenborough (1983).

Still, not four.

Contagion has Matt Damon, Marion Cotillard, Gweneth Paltrow, and Kate Winslet.

It also has nominees Lawrence Fishburne and Jude Law.

Nine (2009) has six: Daniel Day-Lewis (1989, 2007), Judi Dench (1998), Marion Cotillard (2007), Penelope Cruz (2008), Nicole Kidman (2002), and Sophia Loren (1960).

The Dark Knight Rises (2012) has four: (and five total with Anne Hathaway):
Christian Bale (2010), Morgan Freeman (2004), Michael Caine, and Marion Cotillard.

I ask for four, and I get six (but not eggroll)! Daaaaaaang!

The Greatest Story Ever Told, a Biblical epic, featured several people who had already won Oscars:

  1. Jose Ferrer (Best Actor in Cyrano de Bergerac) played Herod Antipas
  2. Charlton Heston (Best Actor in Ben Hur) was John the Baptist
  3. Shelley Winters (Best Supporting Actress in Diary of Anne Frank) was a leper
  4. Van Heflin (Best Supporting Actor for Johnny Eager) was Bar Amand
  5. Sidney Poitier (Best Actor in Lilies of the Field) was Simon of Cyrene
  6. Joseph Schildkraut (Best Supporting Actor in*** Life of Emile Zola***) was Nicodemus

There were also a few FUTURE Oscar winners:

  1. John (True Grit) Wayne was a centurion
  2. Martin Landau (Ed Wood) was Caiaphas

That’s a tiny bit of a cheat, as Damon’s Academy Award is not for acting.

Kenneth Branagh’s Hamlet: Charlton Heston, John Mills, John Gielgud, Jack Lemmon, Julie Christie, Judi Dench, Kate Winslet, Robin Williams, and Richard Attenborough (Director)

The Player (1992)

9 Former Oscar Winners: Cher, Louise Fletcher, Whoopi Goldberg, Joel Grey, Anjelica Huston, Jack Lemmon, Marlee Matlin, Sydney Pollack, Rod Steiger
4 Future Oscar Winners: James Coburn, Tim Robbins, Julia Roberts, Susan Sarandon

13 Total

Hamlet was 1996, so Williams, Dench, and Winslet were not Oscar-winners yet.

That leaves 6 former winners

My bad.

Do these have to be best actor/actress in a *leading *role?

Because I think Judy Dench’s 1998 Oscar was *supporting *(as she said, an award for 6 minutes of screen time).

Interestingly, The Muppet Movie has 6, but only one of those 6 won for acting: Edgar Bergen, Mel Brooks, Bob Hope, Cloris Leachman, Orson Welles, Paul Williams

The documentary Looking for Richard has 7: F. Murray Abraham, John Gielgud, Kevin Kline, Al Pacino, Estelle Parsons, Vanessa Redgrave & Kevin Spacey (all interviews or performance, no archival footage)

The Oscar was a film with 7 as well: Ed Begley, Ernest Borgnine, Walter Brennan, Joan Crawford, James Dunn, Edith Head, Bob Hope, and Frank Sinatra

No. Leading or Supporting…

Films with 5 former winners:
Around the World in 80 Days* (1956) - Charles Coburn, Ronald Colman, Noel Coward, Victor McLaglen, Frank Sinatra
How the West Was Won (1963) - Walter Brennan, Karl Malden, Gregory Peck, Jimmy Stewart, Spencer Tracy

*also featured 5 future winners (John Gielgud, Buster Keaton, Shirley MacLaine, John Mills, David Niven)

***The Poseidon Adventure ***had 5 Oscar winners: Gene Hackman, Ernest Borgnine, Jack Albertson, Shelley Winters and Red Buttons.