Suggestions by @maxcarter

Judy Garland

as Marshmallow in Annoying Orange In The Golden Age Of Hollywood

James Stewart

as Midget Apple in Annoying Orange In The Golden Age Of Hollywood

Claude Rains

as Pear in Annoying Orange In The Golden Age Of Hollywood

Conrad Veidt

as Orange in Annoying Orange In The Golden Age Of Hollywood

Lionel Barrymore

as O.J. in Classic Hero Actors as Modern Heros

Pennywise (It)

as Ennard in Five Nights at Bowser's

Ben Solo (Kylo Ren)

as Funtime Foxy in Five Nights at Bowser's

Miles "Tails" Prower

as Bon-Bon in Five Nights at Bowser's

Bruce The Shark (Jaws)

as Funtime Freddy in Five Nights at Bowser's

Daisy (Thomas and Friends)

as Ballora in Five Nights at Bowser's

Cyn (Murder Drones)

as Circus Baby in Five Nights at Bowser's

Samara Morgan

as Nightmarionette in Five Nights at Bowser's

Snotty Boy

as Nightmare BB in Five Nights at Bowser's

Boingo

as Plushtrap in Five Nights at Bowser's

King Boo

as Nightmare in Five Nights at Bowser's

Dr. Eggman Nega

as Nightmare Fredbear in Five Nights at Bowser's

Green Goblin (Norman Osborn)

as Nightmare Foxy in Five Nights at Bowser's

Velvette (Hazbin Hotel)

as Nightmare Chica in Five Nights at Bowser's

Spencer (Thomas and Friends)

as Nightmare Bonnie in Five Nights at Bowser's

Dr. Eggman (Dr. Ivo Robotnik)

as Nightmare Freddy in Five Nights at Bowser's