Suggestions by @tommovieguy92

Morgan Saylor

as Sylvie Cooper in Poison Ivy

Desiree Akhavan

as Director in Poison Ivy

Jon Hamm

as Reg Hanley in Lady Sings the Blues

Donald Glover

as Piano Man in Lady Sings the Blues

Mahershala Ali

as Louis McKay in Lady Sings the Blues

Janelle Monáe

as Billie Holiday in Lady Sings the Blues

Barry Jenkins

as Producer in Lady Sings the Blues

Tarell Alvin McCraney

as Writer in Lady Sings the Blues

Barry Jenkins

as Director in Lady Sings the Blues

Jordan Peele

as Director in Police Academy

Ryan Gosling

as Rick in Casablanca

Booboo Stewart

as Brock in Pokemon

Pete Holmes

as Meowth in Pokemon