Suggestions by @maxcarter

Boris Karloff

as Frollo in The Hunchback of Norte Dame (1946)

Katharine Hepburn

as Esmeralda in The Hunchback of Norte Dame (1946)

Spencer Tracy

as Quasimodo in The Hunchback of Norte Dame (1946)

Bela Lugosi

as Ghost Train in Classic Villain Actors as Modern Villains

Twilight Sparkle

as Judy Garland in Characters golden age stars could have played

Judy Garland

as Twilight Sparkle in Classic Hero Actors as Modern Heros

Ennard

as Max Schreck in Characters golden age stars could have played

Circus Baby

as Shirley Temple in Characters golden age stars could have played

Satan (Helluva Boss)

as Boris Karloff in Characters golden age stars could have played

Walt Disney

as Producer in The Little Engine That Could (1943)

Ballora

as Lucille La Verne in Characters golden age stars could have played

Conrad Veidt

as Eagle in The Little Engine That Could (1943)

Lon Chaney

as Cave in The Little Engine That Could (1943)

Shirley Temple

as Jill in The Little Engine That Could (1943)

Donnie Dunagan

as Eric in The Little Engine That Could (1943)

Moe Howard

as Handy Pandy in The Little Engine That Could (1943)

Katharine Hepburn

as Missy in The Little Engine That Could (1943)

Larry Fine

as Jeepers in The Little Engine That Could (1943)

Cary Grant

as Stretch in The Little Engine That Could (1943)

Clara Blandick

as Grumpella in The Little Engine That Could (1943)