Suggestions by @jameseller

Moulin Rouge!

as Best Picture 1953 in Oscars Do-over

Cecil B. DeMille

as Best Director 1953 in Oscars Do-over

Gary Cooper

as Best Actor 1953 in Oscars Do-over

Joan Crawford

as Best Actress 1953 in Oscars Do-over

Jack Palance

as Best Supporting Actor 1953 in Oscars Do-over

Thelma Ritter

as Best Supporting Actress 1953 in Oscars Do-over

Julius Caesar

as Best Picture 1954 in Oscars Do-over

Fred Zinnemann

as Best Director 1954 in Oscars Do-over

Montgomery Clift

as Best Actor 1954 in Oscars Do-over

Ava Gardner

as Best Actress 1954 in Oscars Do-over

Frank Sinatra

as Best Supporting Actor 1954 in Oscars Do-over

Grace Kelly

as Best Supporting Actress 1954 in Oscars Do-over

The Country Girl

as Best Picture 1955 in Oscars Do-over

Alfred Hitchcock

as Best Director 1955 in Oscars Do-over

Bing Crosby

as Best Actor 1955 in Oscars Do-over

Judy Garland

as Best Actress 1955 in Oscars Do-over

Lee J. Cobb

as Best Supporting Actor 1955 in Oscars Do-over

Eva Marie Saint

as Best Supporting Actress 1955 in Oscars Do-over

Marty

as Best Picture 1956 in Oscars Do-over

David Lean

as Best Director 1956 in Oscars Do-over