Suggestions by @maxcarter

Theodore Peterson

as Boris Karloff in Characters golden age stars could have played

Mae West

as Susan the Lady Locomotive in The Little Engine That Could 2 Return of the Railroad (1945)

Tobias (TATAM)

as C. Aubrey Smith in Characters golden age stars could have played

Conrad Veidt

as Eagle in The Little Engine That Could 2 Return of the Railroad (1945)

Lon Chaney

as Cave in The Little Engine That Could 2 Return of the Railroad (1945)

Striker (Helluva Boss)

as John Wayne in Characters golden age stars could have played

Scout

as James Stewart in Characters golden age stars could have played

James Stewart

as Jude in Granny In The Golden Age Of Hollywood

Heavy (Team Fortress)

as George Bancroft in Characters golden age stars could have played

Spy (Team Fortress)

as Claude Rains in Characters golden age stars could have played

Boris Karloff

as Hellfire sung by in The Hunchback of Norte Dame (1946)

Medic

as Boris Karloff in Characters golden age stars could have played

Asmodeus (Helluva Boss)

as Paul Robeson in Characters golden age stars could have played

Fizzarolli

as Conrad Veidt in Characters golden age stars could have played

Beelzebub (Helluva Boss)

as Judy Garland in Characters golden age stars could have played

Mammon (Helluva Boss)

as Roscoe Arbuckle in Characters golden age stars could have played

Paimon (Helluva Boss)

as Lionel Barrymore in Characters golden age stars could have played

Stolas (Helluva Boss)

as Claude Rains in Characters golden age stars could have played

Loona (Helluva Boss)

as Elsa Lanchester in Characters golden age stars could have played

Judy Garland

as Cyn in Classic Villain Actors as Modern Villains