8,293 suggestions
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
Brittany Murphy
as Andie Walsh in Pretty in Pink (1996)
Jonathan Brandis
as Anthony Michael Hall in '80s Actors in the '90s
Ian Ziering
as Emilio Estevez in '80s Actors in the '90s
Winona Ryder
as Ally Sheedy in '80s Actors in the '90s
Jared Leto
as Judd Nelson in '80s Actors in the '90s
