Suggestions by @maxcarter
3,103 suggestions

Cary Grant
as More Than Everything sung by in Hazbin Hotel (1944)
Judy Garland
as Hell's Greatest Dad sung by in Hazbin Hotel (1944)
Claudette Colbert
as Hell's Greatest Dad sung by in Hazbin Hotel (1944)
Bela Lugosi
as Hell's Greatest Dad sung by in Hazbin Hotel (1944)

Cary Grant
as Hell's Greatest Dad sung by in Hazbin Hotel (1944)
William Haines
as Loser, Baby sung by in Hazbin Hotel (1944)

Paul Robeson
as Loser, Baby sung by in Hazbin Hotel (1944)
William Haines
as Poison sung by in Hazbin Hotel (1944)

Edward Van Sloan
as Respectless sung by in Hazbin Hotel (1944)
Lucille La Verne
as Respectless sung by in Hazbin Hotel (1944)

Mae West
as Respectless sung by in Hazbin Hotel (1944)
William Haines
as It Starts With Sorry sung by in Hazbin Hotel (1944)
Judy Garland
as It Starts With Sorry sung by in Hazbin Hotel (1944)
Fay Wray
as It Starts With Sorry sung by in Hazbin Hotel (1944)

Lionel Barrymore
as It Starts With Sorry sung by in Hazbin Hotel (1944)
Claude Rains
as Stayed Gone sung by in Hazbin Hotel (1944)

Conrad Veidt
as Hell Is Forever sung by in Hazbin Hotel (1944)
Judy Garland
as Happy Day In Hell sung by in Hazbin Hotel (1944)

Murdoch (Thomas and Friends)
as Paul Robeson in Characters golden age stars could have played

Mavis (Thomas and Friends)
as Lucille Ball in Characters golden age stars could have played