Suggestions by @maxcarter

Shemp Howard

as Rollo in The Little Engine That Could (1943)

Edward Van Sloan

as Doc in The Little Engine That Could (1943)

Lucille La Verne

as Georgia in The Little Engine That Could (1943)

Paul Robeson

as Pete in The Little Engine That Could (1943)

Charley Grapewin

as Jebediah in The Little Engine That Could (1943)

Paul Robeson

as Pete in The Little Engine That Could (1943)

Boris Karloff

as Farnsworth in The Little Engine That Could (1943)

Lionel Barrymore

as Tower in The Little Engine That Could (1943)

Dickie Jones

as Chip in The Little Engine That Could (1943)

Judy Garland

as Tillie in The Little Engine That Could (1943)

Frank Welker

as 5.0.5 in Villainous (Live-Action)

Tara Strong

as Dementia in Villainous (Live-Action)

Joseph May

as Dr. Flug Slys in Villainous (Live-Action)

Jonathan Freeman

as Black Hat in Villainous (Live-Action)

Shemp Howard

as Demon Stooge 4 in Hazbin Hotel (1944)

Larry Fine

as Demon Stooge 3 in Hazbin Hotel (1944)

Moe Howard

as Demon Stooge 1 in Hazbin Hotel (1944)

Erich von Stroheim

as Kaa in Classic Villain Actors as Modern Villains

Peter Cullen

as Gordon the Big Express engine in Thomas the Tank Engine the Movie (1992)

Lucifer Morningstar (Hazbin Hotel and Helluva Boss)

as Cary Grant in Characters golden age stars could have played