Suggestions by @randomcaster

Dee Reynolds

as Kaitlin Olson in Best character each of these actors played

Ronald "Mac" McDonald

as Rob McElhenney in Best character each of these actors played

Dennis Reynolds

as Glenn Howerton in Best character each of these actors played

Alfred Pennyworth

as Michael Caine in Best character each of these actors played

Rango

as Johnny Depp in Best character each of these actors played

Freddy Krueger

as Robert Englund in Best character each of these actors played

Lydia Deetz

as Winona Ryder in Best character each of these actors played

Eleven

as Millie Bobby Brown in Best character each of these actors played

Kronk

as Patrick Warburton in Best character each of these actors played

Deadpool (Marvel Cinematic Universe)

as Ryan Reynolds in Best character each of these actors played

Corny Collins

as James Marsden in Best character each of these actors played

Sonic the Hedgehog

as Ben Schwartz in Best character each of these actors played

Emperor Kuzco

as David Spade in Best character each of these actors played

Paul Blart

as Kevin James in Best character each of these actors played

Uncle Ruckus

as Gary Anthony Williams in Best character each of these actors played

Drax the Destroyer

as Dave Bautista in Best character each of these actors played

Iago

as Gilbert Gottfried in Best character each of these actors played

Rocket Raccoon (Marvel Cinematic Universe)

as Bradley Cooper in Best character each of these actors played

Groot (Marvel Cinematic Universe)

as Vin Diesel in Best character each of these actors played

Pennywise (It)

as Bill Skarsgård in Best character each of these actors played