Suggestions by @timemachine
8,267 suggestions
Heather Locklear
as Fern "Vylette" Mayo in Jawbreaker (1984)
Heather Locklear
as Annette Hargrove in Cruel Intentions (1984)
Emilio Estevez
as Sebastian Valmont in Cruel Intentions (1984)
Kim Delaney
as Kathryn Merteuil in Cruel Intentions (1984)
Phoebe Cates
as Elizabeth "Liz" Purr in Jawbreaker (1984)
Helen Hunt
as Marcie "Foxy" Fox in Jawbreaker (1984)
Genie Francis
as Julie Freeman in Jawbreaker (1984)
Heather Langenkamp
as Courtney Shayne in Jawbreaker (1984)
Ariana Richards
as Duckette in Pretty in Pink (1996)
Larisa Oleynik
as Amber Mariens in Clueless (2000)
Lacey Chabert
as Tai Frasier in Clueless (2000)
Gabrielle Union
as Dionne Davenport in Clueless (2000)
Kate Hudson
as Cher Horowitz in Clueless (2000)
Amy Poehler
as Iona in Pretty in Pink (2006)
Tom Welling
as Blane McDonough in Pretty in Pink (2006)
Jared Padalecki
as Steff McKee in Pretty in Pink (2006)
Michael Cera
as Phillip F. Dale in Pretty in Pink (2006)
Tom Cruise
as Zach Siler in She's All That (1984)
Diane Lane
as Taylor Vaughan in She's All That (1984)
Kim Cattrall
as Josie Geller in Never Been Kissed (1984)