Suggestions by @adamatc
3,417 suggestions
Tom Cruise
as Frank Sinatra in Sinatra (Biopic)

Mary Elizabeth Winstead
as Ava Gardner in Sinatra (Biopic)
Carey Mulligan
as Mia Farrow in A Short Marriage That Ended with A Divorce in Mexico

Miles Teller
as Dean Martin in My Way

Mary Elizabeth Winstead
as Ava Gardner in My Way
Tom Cruise
as Frank Sinatra in Just good buddies

Mary Elizabeth Winstead
as Ava Gardner in Just good buddies

Miles Teller
as Dean Martin in Chairman of the Board
Carey Mulligan
as Mia Farrow in Chairman of the Board
Tom Cruise
as Frank Sinatra in Chairman of the Board

Olivia Wilde
as Elizabeth Taylor in Hollywood Goddesses

Heather Graham
as Bette Davis in Hollywood Goddesses

Mary Elizabeth Winstead
as Ava Gardner in Hollywood Goddesses

Gerald Di Pego
as Writer in Two for the Money (1986)

John Badham
as Director in Two for the Money (1986)

Ann-Margret
as Toni Abrams in Two for the Money (1986)
Tom Cruise
as Brandon Lang/John Anthony in Two for the Money (1986)

Marlon Brando
as Walter Abrams in Two for the Money (1986)
Eric Red
as Writer in The Old Guard (1990)
Kathryn Bigelow
as Director in The Old Guard (1990)