Suggestions by @adrianpintado

Richard Dreyfuss

as George Nelson in O Brother, Where Art Thou? (1970)

Jack Elam

as Washington Bartholomew Hogwallop in O Brother, Where Art Thou? (1970)

Cleavon Little

as Tommy Johnson in O Brother, Where Art Thou? (1970)

Kenneth Mars

as Vernon T. Waldrip in O Brother, Where Art Thou? (1970)

Ned Beatty

as Homer Stokes in O Brother, Where Art Thou? (1970)

Morgan Woodward

as Sheriff Cooley in O Brother, Where Art Thou? (1970)

Dub Taylor

as "Pappy" O'Daniel in O Brother, Where Art Thou? (1970)

Cloris Leachman

as Penny Wharvey-McGill in O Brother, Where Art Thou? (1970)

Orson Welles

as Daniel "Big Dan" Teague in O Brother, Where Art Thou? (1970)

Robert Duvall

as Pete Hogwallop in O Brother, Where Art Thou? (1970)

Gene Hackman

as Pete Hogwallop in O Brother, Where Art Thou? (1970)

Gene Wilder

as Delmar O'Donnell in O Brother, Where Art Thou? (1970)

Paul Newman

as Ulysses Everett McGill in O Brother, Where Art Thou? (1970)

Robert Duvall

as Micah Bell in Red Dead Redemption (1970's)

Robert Duvall

as Micah Bell in Red Dead Redemption (1960's)

Robert Duvall

as Edgar Ross in Red Dead Redemption (1980's)

Robert Duvall

as Andrew Milton in Red Dead Redemption (1980's)

Robert Duvall

as Edgar Ross in Red Dead Redemption (1970's)

Gene Hackman

as Edgar Ross in Red Dead Redemption (1970's)

Robert Duvall

as Andrew Milton in Red Dead Redemption (1970's)