Suggestions by @masterofcool

Tom Cruise

as Dominic Cobb in Inception (2000)

Sandra Bullock

as Detective Ellen Burr in Insomnia (1992)

Steve Martin

as Walter Finch in Insomnia (1992)

Marlon Brando

as Louis Cyphre in Angel Heart (1972)

Gregory Peck

as Harlan Thrombey in Knives Out (1999)

Willem Dafoe

as Walter Thrombey in Knives Out (1999)

Brad Renfro

as Jacob Thrombey in Knives Out (1999)

Melinda Dillon

as Linda Drysdale in Knives Out (1999)

Will Smith

as Detective Lieutenant James Elliott in Knives Out (1999)

Brad Pitt

as Hugh Ransom Drysdale in Knives Out (1999)

Sam Neill

as Detective Benoit Blanc in Knives Out (1999)

Samuel L. Jackson

as Dr. Facilier in The Princess and the Frog (1999)

Isabella Rossellini

as Madison Lee in Charlie's Angels Trilogy (1990-1993)

Sandra Bullock

as Dylan Sanders in Charlie's Angels Trilogy (1990-1993)

Chevy Chase

as John Bosley in Charlie's Angels Trilogy (1990-1993)

Heather Locklear

as Natalie Cook in Charlie's Angels Trilogy (1990-1993)

Jim Carrey

as Charles Winston in Charlie's Angels Trilogy (1990-1993)

Michael Caine

as Roger Corwin in Charlie's Angels Trilogy (1990-1993)

Danny Glover

as Principal Ronald Duvall in Mean Girls (1994)

Gary Oldman

as Harlen Maguire in Road to Perdition (1992)