Movies with the most future Oscar winners

Watching Fast Times at Ridgemont High I was reminded that future Oscar winners Nic Cage, Sean Penn, and Forest Whitaker were among the cast. Not to mention frequently overlooked Jennifer Jason Leigh. Any other movies with a similar pedigree? Google was unhelpful.

Although none of these actors won a Oscar, a movie that was excellent at featuring actors who wouldn’t become well known until later was the 1983 film The Outsiders, whose cast included C. Thomas Howell, Matt Dillon, Ralph Macchio, Patrick Swayze, Rob Lowe, Emilio Estevez, Tom Cruise, Diane Lane, and Sofia Coppola.

Beau Geste (1939) and Winged Victory (1944) have four future winners each.

Beau Geste: Gary Cooper, Ray Milland, Susan Hayward and Broderick Crawford.

Winged Victory: Edmond O’Brien, Red Buttons, Judy Holliday and Karl Malden.

None of them had won prior?

Four in THE LONGEST DAY: Sean Connery (who later got it for THE UNTOUCHABLES), John Wayne (TRUE GRIT), Rod Steiger (IN THE HEAT OF THE NIGHT), and Henry Fonda (ON GOLDEN POND).

Angels in the Outfield, the 1994 version, had one active Oscar winner (Brenda Fricker) and two future winners (Adrien Brody, Matthew McConaughey) in its cast. Not to mention Danny Glover and Joseph Gordon-Levitt as well. Neal McDonough was also in that film.

Nope. Gary Cooper had been nominated for Mr. Deeds Goes to Town but that’s it.

The Thin Red Line: George Clooney, Sean Penn, Adrien Brody, Jared Leto.

The Greatest Story Ever Told (1965) also had 4 future Oscar winners (Max Von Sydow(Pelle the Conqueror, 1987), John Wayne(True Grit, 1969), Shelley Winters(A Patch of Blue, 1965), Martin Landau(Ed Wood, 1994)

It also had a trio of prior Oscar winners- Charlton Heston, Joseph Schildkraut and Jose Ferrer .

I remember this coming up before, but it’s been a looong time:

Winters won two oscars: Diary of Anne Frank, 1959, and A Patch of Blue, 1965. Nominated twice more. Shoulda won for A Place in the Sun.

Five for Woody Allen’s CELEBRITY: Leonardo DiCaprio, Allison Janney, Sam Rockwell, JK Simmons, and Charlize Theron.

Godfather Part 2 had Al Pacino, Robert Duvall, Diane Keaton, and Robert De Niro

The Stolen Jools had Gary Cooper, Victor McLaglen, Loretta Young, Wallace Beery, and Joan Crawford — along with Stan Laurel and Edward G. Robinson and Barbara Stanwyck and Maurice Chevalier and Buster Keaton, each of whom later got an honorary-award statuette.

(Charles ‘Buddy’ Rogers arguably counts too.)

Yeah, I counted her as a “future Oscar winner” for purposes of the movie, as when it was released, she had yet to win her second Oscar (that same year for a different movie in fact).