Suggestions by @luahshin
269 suggestions

Miranda Priestly
as Grace Kelly in Characters golden age stars could have played

Boom Boom (Tabitha Smith)
as Marilyn Monroe in Characters golden age stars could have played

Magik (Illyana Rasputina)
as Shirley Temple in Characters golden age stars could have played
Mamie Van Doren
as 1950s in What Actresses Could've Played Regina George in Various Decades?
Joan Fontaine
as 1950s in What Actresses Could've Played Regina George in Various Decades?

Jayne Mansfield
as 1950s in What Actresses Could've Played Regina George in Various Decades?
Barbara Stanwyck
as 1950s in What Actresses Could've Played Regina George in Various Decades?

Mae West
as 1920s in What Actresses Could've Played Regina George in Various Decades?
Esther Williams
as Princess Ariel in The Little Mermaid (1940s)
Irene Papas
as Moana in Classic Actors As Modern Movie characters
Diahann Carroll
as Moana in Classic Actors As Modern Movie characters

Nina Mae McKinney
as Moana in Classic Actors As Modern Movie characters
Olivia de Havilland
as 1960s in Actresses who could play Arwen

Angela Lansbury
as 1960s in Actresses who could play Arwen
Judy Garland
as 1950s in Actresses who could play Arwen

Paige Matthews
as Judy Garland in Which Throwback Characters Could Actors Have Played

Danielle Panabaker
as Peter Parker in Marvel Comics (Gender Swap)
Kim Novak
as Cher Horowitz in Clueless (1940)
Yoshiko Yamaguchi
as Gogo Yubari in Kill Bill: Volume 1 (1963)
Ingrid Bergman
as Elle Driver in Kill Bill: Volume 1 (1963)