Suggestions by @sammartin

Burt Reynolds

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

Clint Eastwood

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

Danny DeVito

as George Nelson in O Brother, Where Art Thou (1985)

Jerry O'Connell

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

Barry White

as Gravedigger 3 in O Brother, Where Art Thou (1985)

Isaac Hayes

as Gravedigger 3 in O Brother, Where Art Thou (1985)

Little Richard

as Gravedigger 2 in O Brother, Where Art Thou (1985)

B.B. King

as Gravedigger 1 in O Brother, Where Art Thou (1985)

Michael J. Anderson

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

Michael J. Anderson

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

David Rappaport

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

Danny DeVito

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

Ray Liotta

as George Nelson in O Brother, Where Art Thou (1985)

Billy Crystal

as George Nelson in O Brother, Where Art Thou (1985)

Joe Pesci

as George Nelson in O Brother, Where Art Thou (1985)

Alan Silvestri

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

Dennis Hopper

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

Tom Hanks

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

Eugene Levy

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

Stephen King

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