Suggestions by @timemachine

Tobey Maguire

as Josh Detmer in Freaky (2000)

Matthew Lillard

as Booker Strode in Freaky (Late '90s)

Johnny Depp

as Booker Strode in Freaky (1990)

Will Friedle

as Josh Detmer in Freaky (Late '90s)

Leonardo DiCaprio

as Josh Detmer in Freaky (1995)

Keanu Reeves

as Josh Detmer in Freaky (1990)

Danny Elfman

as Composer in The Grim Adventures of Billy & Mandy ('90s live-action movie)

Tim Burton

as Producer in The Grim Adventures of Billy & Mandy ('90s live-action movie)

Tim Burton

as Director in The Grim Adventures of Billy & Mandy ('90s live-action movie)

Geena Davis

as Mrs. Butterbean in The Grim Adventures of Billy & Mandy ('90s live-action movie)

David Krumholtz

as Nergal Jr. in The Grim Adventures of Billy & Mandy ('90s live-action movie)

Annie Potts

as Aunt Sis in The Grim Adventures of Billy & Mandy ('90s live-action movie)

Michael Keaton

as Nergal in The Grim Adventures of Billy & Mandy ('90s live-action movie)

Alec Baldwin

as Phillip in The Grim Adventures of Billy & Mandy ('90s live-action movie)

Kurt Russell

as Hoss Delgado in The Grim Adventures of Billy & Mandy ('90s live-action movie)

Sarah Jessica Parker

as Eris in The Grim Adventures of Billy & Mandy ('90s live-action movie)

Michelle Pfeiffer

as Claire in The Grim Adventures of Billy & Mandy ('90s live-action movie)

Catherine O'Hara

as Gladys in The Grim Adventures of Billy & Mandy ('90s live-action movie)

Chris Farley

as Harold in The Grim Adventures of Billy & Mandy ('90s live-action movie)

Joseph Gordon-Levitt

as Piff in The Grim Adventures of Billy & Mandy ('90s live-action movie)