Suggestions by @maxcarter

Hattie McDaniel

as You Didn't Know sung by in Hazbin Hotel (1944)

Score: +3

Shirley Temple

as You Didn't Know sung by in Hazbin Hotel (1944)

Score: +4

Marilyn Monroe

as Whatever It Takes sung by in Hazbin Hotel (1944)

Score: +4

Edward Van Sloan

as Whatever It Takes sung by in Hazbin Hotel (1944)

Score: +4

Lucille La Verne

as Whatever It Takes sung by in Hazbin Hotel (1944)

Score: +4

William Haines

as It's Starts With Sorry sung by in Hazbin Hotel (1944)

Score: +4

Marilyn Monroe

as It's Starts With Sorry sung by in Hazbin Hotel (1944)

Score: +4

Lionel Barrymore

as It's Starts With Sorry sung by in Hazbin Hotel (1944)

Score: +4

Judy Garland

as It's Starts With Sorry sung by in Hazbin Hotel (1944)

Score: +4

Judy Garland and Marilyn Monroe

as Those Two Actors in Celebrities Sorted by Tropes

Score: +5

Charlie Morningstar

as Hazbin Hotel in All Fictional Characters Sorted by Media

Score: +6

Charlie Morningstar

as Judy Garland in Modern Characters as Classic Actors

Score: -2

Marilyn Monroe

as Vaggie in The Vees (1945)

Score: +3

Marilyn Monroe

as Vaggie in Hazbin Hotel (1944)

Score: -2

Bill Fagerbakke

as Thepinkmenace in maxcarter's Crackcrossover (2025)

Score: +4

Rick Astley

as Rickatvo2009 in maxcarter's Crackcrossover (2025)

Score: +3

Gal Gadot

as Lilith Morningstar in Hazbin Hotel (2024 Rescast)

Score: +3

Katharine Hepburn

as Buster's Mother in We're Back! A Dinosaur's Story (1943)

Score: +4

Donnie Dunagan

as Buster in We're Back! A Dinosaur's Story (1943)

Score: +4

Charlie Chaplin

as Vorb in We're Back! A Dinosaur's Story (1943)

Score: +4