Suggestions by @sammartin

David Lynch

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

Harry Shearer

as Mr. Lund in O Brother, Where Art Thou (1985)

Jim Belushi

as Washington Bartholomew Hogwallop in O Brother, Where Art Thou (1985)

Christopher Guest

as Vernon T. Waldrip in O Brother, Where Art Thou (1985)

Dana Carvey

as Vernon T. Waldrip in O Brother, Where Art Thou (1985)

Michael Keaton

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

Gene Wilder

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

Randy Quaid

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

Martin Short

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

Rick Moranis

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

Randy Quaid

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

Brian Doyle-Murray

as Vernon T. Waldrip in O Brother, Where Art Thou (1985)

Robert Duvall

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

David Lynch

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

Wallace Shawn

as Homer Stokes in O Brother, Where Art Thou (1985)

Dan Aykroyd

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

Ossie Davis

as Blind Seer in O Brother, Where Art Thou (1985)

Bill Murray

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

Harry Dean Stanton

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

Bill Murray

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