Suggestions by @maxcarter
3,103 suggestions

Clark Gable
as A.M. in Hazbin Hotel (1944)
Edward Everett Horton
as Beburos in Hazbin Hotel (1944)
Lionel Atwill
as Great Comrade in Hazbin Hotel (1944)

Oliver Hardy
as Cletus in Helluva Boss (1940-1944)

Joan Crawford
as Keenie in Helluva Boss (1940-1944)

Stan Laurel
as Collin in Helluva Boss (1940-1944)
Paul Robeson
as Asmodeus in Helluva Boss (1940-1944)
Boris Karloff
as Satan in Helluva Boss (1940-1944)

Lionel Barrymore
as Paimon in Helluva Boss (1940-1944)
Charley Grapewin
as Rolando in Helluva Boss (1940-1944)
Evelyn Nesbit
as Glam in Helluva Boss (1940-1944)
Hedy Lamarr
as Glitz in Helluva Boss (1940-1944)
Roscoe Arbuckle
as Mammon in Helluva Boss (1940-1944)
Judy Garland
as Beelzebub in Helluva Boss (1940-1944)
Bela Lugosi
as Crimson in Helluva Boss (1940-1944)
Claudette Colbert
as Agent 2 in Helluva Boss (1940-1944)

Clark Gable
as Agent 1 in Helluva Boss (1940-1944)
Vincent Price
as Wally Wackford in Helluva Boss (1940-1944)

John Wayne
as Striker in Helluva Boss (1940-1944)
Lucille Ball
as Verosika Mayday in Helluva Boss (1940-1944)