Suggestions by @shekothearabicwarrior

Walter Matthau

as Director in Monty python’s Sherlock Holmes

Danny DeVito

as Director in Monty python’s Sherlock Holmes

Terry Gilliam

as Director in Monty python’s Sherlock Holmes

Kirsten Dunst

as Judy Shepherd in Jumanji (1995/Deleted Scenes/Alternate Versions)

Daniel Craig

as Jumanji in Actors who should be in / join certain Cinematic Universe

Pierce Brosnan

as Jumanji in Actors who should be in / join certain Cinematic Universe

Russell Crowe

as Jumanji in Actors who should join certain big franchises

Clive Revill

as Fredrick the Megalodon in Shark Tale (2004/Deleted Scenes/Alternate Versions)

John Hughes

as Writer in Paddington (1994)

Howard Deutch

as Producer in Paddington (1994)

John Hughes

as Producer in Paddington (1994)

Greg Beeman

as Director in Paddington (1994)

Basil Poledouris

as Composer in Sleepover (1994)

Rob Reiner

as Writer in Sleepover (1994)

Suzanne Todd

as Producer in Sleepover (1994)

Jennifer Todd

as Producer in Sleepover (1994)

Demi Moore

as Producer in Sleepover (1994)

Mike Myers

as Producer in Sleepover (1994)

Frank Oz

as Producer in Sleepover (1994)

Stephen Herek

as Director in Popeye (Michael Stuhlbarg and Lady Gaga remake film)