Suggestions by @timemachine
8,267 suggestions
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
Olivia Hack
as Molly Ringwald in '80s Actors in the '90s
Judd Nelson
as Jared Leto in '90s Actors in the '80s
Kim Cattrall
as Drew Barrymore in '90s Actors in the '80s
Brooke Shields
as Rachael Leigh Cook in '90s Actors in the '80s
Ally Sheedy
as Winona Ryder in '90s Actors in the '80s
Matt Dillon
as Heath Ledger in '90s Actors in the '80s