Suggestions by @timemachine
8,238 suggestions
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)
Brooke Shields
as Laney Boggs in She's All That (1984)
Jon Cryer
as Leonardo DiCaprio in '90s Actors in the '80s
Casey Affleck
as Ralph Macchio in '80s Actors in the '90s
Christina Applegate
as Benny Hanson in Pretty in Pink (1996)
Brian Austin Green
as Blane McDonough in Pretty in Pink (1996)
Matthew McConaughey
as Steff McKee in Pretty in Pink (1996)
Kelly Preston
as Iona in Pretty in Pink (1996)
Leonardo DiCaprio
as Philip F. Dale in Pretty in Pink (1996)
Leonardo DiCaprio
as Jon Cryer in '80s Actors in the '90s