Suggestions by @pakjirasan

Betsy Russell

as Lilly (My Super Psycho Sweet 16) in Actors That Should've Played Character in the 80's

Olivia D'Abo

as Madison Penrose in Actors That Should've Played Character in the 80's

Winona Ryder

as Skye Rotter in Actors That Should've Played Character in the 80's

Heather Locklear

as Regina George in Actors That Should've Played Character in the 80's

Elisabeth Shue

as Karen Smith in Actors That Should've Played Character in the 80's

Renee Murphy

as Rhonda Wilson in Actors That Should've Played Character in the 80's

Samantha Logan

as Cora Wilson in Actors That Should've Played Character in the 80's

Olivia D'Abo

as Carrie White in Actors That Should've Played Character in the 80's

Molly Ringwald

as Max Mayfield in Actors That Should've Played Character in the 80's

Mia Sara

as Nancy Wheeler in Actors That Should've Played Character in the 80's

Jennifer Grey

as Nancy Wheeler in Actors That Should've Played Character in the 80's

Winona Ryder

as Eleven in Actors That Should've Played Character in the 80's

Aaliyah

as Rue Bennett in Actors That Should've Played Characters in the '90s

Leonardo DiCaprio

as Tommy Ross in Actors That Should've Played Characters in the '90s

Robin Tunney

as Skye Rotter in Actors That Should've Played Characters in the '90s

Gabrielle Union

as Olivia (My Super Psycho Sweet 16) in Actors That Should've Played Characters in the '90s

Christina Ricci

as Jennifer Baylor in Actors That Should've Played Characters in the '90s

Christine Taylor

as Angela (Stranger Things) in Actors That Should've Played Characters in the '90s

Emily Bergl

as Lilly (My Super Psycho Sweet 16) in Actors That Should've Played Characters in the '90s

Rachael Leigh Cook

as Lilly (My Super Psycho Sweet 16) in Actors That Should've Played Characters in the '90s