Suggestions by @enzoooo

Forest Whitaker

as Lawnmower Larry in Happy Wheels: The Movie

Jim Carrey

as Irresponsible Dad in Happy Wheels: The Movie

Katherine Langford

as Anna Lestrange in A Year at Hogwarts

Anthony Boyle

as Scorpius Malfoy in A Year at Hogwarts

Timothée Chalamet

as Tobias Lestrange in A Year at Hogwarts

Rocco Siffredi

as John F. Kennedy in 11/22/63

Rupert Grint

as Hermann Goring in Hitler: The Man, The Myth, The Legend

Beyoncé

as Benito Mussolini the Fat Entitled Italian Fuck in Hitler: The Man, The Myth, The Legend

Jim Carrey

as Adolf Hitler in Hitler: The Man, The Myth, The Legend

Sean Penn

as Emperor Palpatine in Star Wars

Laurence Fishburne

as Martin Luther King jr in Harriet

Dustin Hoffman

as Leonard Cohen in Hallelujah

Claudia Kim

as Yoko Ono in The Beatles Biopic