Suggestions by @laitgirl

Gary Cooper

as Rhett Butler in Gone with the Wind

Ruby Dandridge

as Mammy in Gone with the Wind

Joan Blondell

as Belle Watling in Gone with the Wind

Laurence Olivier

as Ashley Hamilton in Gone with the Wind

Ann Dvorak

as Melanie Hamilton (nee Wilkes) in Gone with the Wind

Joan Blondell

as Melanie Hamilton (nee Wilkes) in Gone with the Wind

Loretta Young

as Scarlett O'Hara in Gone with the Wind

Gary Oldman

as Bobby in A Star Is Born (2002)

Wilson Cruz

as Ramon in A Star Is Born (2002)

Hugh Grant

as Rez Gavron in A Star Is Born (2002)

Ewan McGregor

as Norman Maine in A Star Is Born (2002)

P!nk

as Vicki Lester in A Star Is Born (2002)

Jane Fonda

as Helen Lawson in Valley Of The Dolls (1987)

Anjelica Huston

as Miriam Polar in Valley Of The Dolls (1987)

Jon Bon Jovi

as Tony Polar in Valley Of The Dolls (1987)

Pierce Brosnan

as Lyon Burke in Valley Of The Dolls (1987)

Sharon Stone

as Jennifer North in Valley Of The Dolls (1987)

Diane Lane

as Anne Welles in Valley Of The Dolls (1987)

Jodie Foster

as Neely O'Hara in Valley Of The Dolls (1987)