Suggestions by @timemachine
8,267 suggestions
Reese Witherspoon
as Keith "Two-Bit" Matthews in The Outsiders ('90s Genderswap/Genderbent)
Raven-Symoné
as Dee Thomas in What's Happening!! (1996-1999)
Sean Nelson
as Dwayne Clemens Nelson in What's Happening!! (1996-1999)
Will Smith
as Roger Thomas in What's Happening!! (1996-1999)
Kenan Thompson
as Frederick "Freddy" Stubbs in What's Happening!! (1996-1999)
Matthew Lawrence
as Jordan Kent in Superman & Lois (90's)
Joey Lawrence
as Jonathan Kent in Superman & Lois (90's)
Teri Hatcher
as Lois Lane in Superman & Lois (90's)
Dean Cain
as Superman in Superman & Lois (90's)
Jennifer Love Hewitt
as Sherri Valance in The Outsiders (1998)
Tobey Maguire
as Steve Randle in The Outsiders (1998)
Nicholas Brendon
as Keith Matthews in The Outsiders (1998)
Jensen Ackles
as Sodapop Curtis in The Outsiders (1998)
Freddie Prinze Jr.
as Darrel Curtis in The Outsiders (1998)
Joseph Gordon-Levitt
as Johnny Cade in The Outsiders (1998)
Leonardo DiCaprio
as Dallas "Dally" Winston in The Outsiders (1998)
Drew Barrymore
as Lydia Deetz in Beetlejuice (1993)
Michelle Pfeiffer
as Barbara Maitland in Beetlejuice (1993)
Dana Carvey
as Adam Maitland in Beetlejuice (1993)
Jim Carrey
as Beetlejuice in Beetlejuice (1993)