Suggestions by @sammartin

Rob Reiner

as Director in O Brother, Where Art Thou (1985)

Carl Reiner

as Menelaus O'Daniel in O Brother, Where Art Thou (1985)

Mel Brooks

as Menelaus O'Daniel in O Brother, Where Art Thou (1985)

Gene Wilder

as Pete in O Brother, Where Art Thou (1985)

Orson Welles

as Menelaus O'Daniel in O Brother, Where Art Thou (1985)

Robert Zemeckis

as Director in O Brother, Where Art Thou (1985)

Harold Ramis

as Director in O Brother, Where Art Thou (1985)

R. Lee Ermey

as Sheriff Cooley in O Brother, Where Art Thou (1985)

John Candy

as Dan Teague in O Brother, Where Art Thou (1985)

Prince

as Tommy Johnson in O Brother, Where Art Thou (1985)

Karen Allen

as Penny Wharvey-McGill in O Brother, Where Art Thou (1985)

Martin Short

as Delmar O'Donnell in O Brother, Where Art Thou (1985)

Chevy Chase

as Ulysses Everett McGill in O Brother, Where Art Thou (1985)

Steve Martin

as Ulysses Everett McGill in O Brother, Where Art Thou (1985)

Caleb Landry Jones

as Bill Carson in The Good, The Bad, and the Ugly (2022)

Sebastian Stan

as Blondie in The Good, The Bad, and the Ugly (2022)

Michael Giacchino

as Composer in The Good, The Bad, and the Ugly (2022)

Roger Deakins

as Cinematographer in The Good, The Bad, and the Ugly (2022)

Quentin Tarantino

as Executive Producer in The Good, The Bad, and the Ugly (2022)

Clint Eastwood

as Producer in The Good, The Bad, and the Ugly (2022)