Suggestions by @siddarthsid

Jim Carrey

as Carl Spackler in Caddyshack (1990)

Uma Thurman

as Blanche in Drive (2001)

Javier Bardem

as Standard Gabriel in Drive (2001)

David Cronenberg

as Director in Mandy (1990's)

Steven Soderbergh

as Director in Drive (2001)

Dennis Farina

as Nino in Drive (2001)

Elliott Gould

as Bernie Rose in Drive (2001)

Laura Harring

as Blanche in Drive (2001)

Benicio del Toro

as Standard Gabriel in Drive (2001)

William H. Macy

as Shannon in Drive (2001)

Kelly Macdonald

as Irene in Drive (2001)

Matthew McConaughey

as The Driver in Drive (2001)

Amy Adams

as Karen Hill in Goodfellas (2010)

James Gandolfini

as Paulie Cicero in Goodfellas (2010)

Kate Winslet

as Karen Hill in Goodfellas (2010)

Steve Buscemi

as Billy Bats in Goodfellas (2010)

James Earl Jones

as Major Grant in Die Hard 2 (1980)

Natalie Portman

as Cobb in Inception (Gender-Swap)

Joaquin Phoenix

as Henry Hill in Goodfellas (2010)

Robert Downey Jr.

as Jimmy Conway in Goodfellas (2010)