John Cazale was never nominated 
Reds nominations: Warren Beatty (14), Jack Nicholson (12), Gene Hackman (5) Diane Keaton (4), Maureen Stapleton (4), Bessie Love = 40 nominations
Walt Disney himself won 22 Oscars, and had 59 nominations.
Manhattan nominations: Woody Allen (23), Meryl Streep (17), Diane Keaton (4), Mariel Hemingway = 45 nominations
Casino Royale nominations: Woody Allen (23), John Huston (15), Peter O’Toole (8), Deborah Kerr (6), Charles Boyer (4), William Holden (3), Orson Welles (3), Peter Sellers (2), David Niven = 65 nominations.
This will be very tough to beat.
The Biblical epic The Greatest Storyt Ever Told had numerous Oscar winners AND numerous future Oscar winners.
Jose “Herod Antipas” Ferrer
Van “Bar Anand” Heflin
Charlton “John the Baptist” Heston
Martin “Caiaphas” Landau
Sidney “Simon of Cyrene” Poitier
Joseph “Nicodemus” Schildkraut
John “Centurion” Wayne
Shelley “Cured Woman” Winters (2)
Not a question, but if there were a category for TV shows (i.e. not miniseries or movies but series) would probably be Roseanne, which had at least three winners with four Oscars as recurring characters: Estelle Parsons (1), Shelley Winters (2) and Red Buttons (1), though only Parsons was ever a regular.
***The Simpsons ***blows that away with guest stars. Even with recurring characters or better, Maggie has been voiced by both Elizabeth Taylor (2 wins) and Jodie Foster (2 wins), and Meryl Streep (3 wins) voiced Jessica Lovejoy.