Suggestions by @timemachine
8,238 suggestions
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
Elisabeth Shue
as Larisa Oleynik in '90s Actors in the '80s
Jodie Foster
as Julia Stiles in '90s Actors in the '80s
Molly Ringwald
as Elisa Donovan in '90s Actors in the '80s
Heather Langenkamp
as Brittany Murphy in '90s Actors in the '80s
Robin Givens
as Stacey Dash in '90s Actors in the '80s
Heather Locklear
as Alicia Silverstone in '90s Actors in the '80s
Stefanie Powers
as Addison Montgomery in Grey's Anatomy (1985-2001)
Tony Danza
as Derek Shepherd in Grey's Anatomy (1985-2001)
Ernie Hudson
as Richard Webber in Grey's Anatomy (1985-2001)