Suggestions by @christopher00h
3,106 suggestions

Mara Wilson
as Mayor's Daughters in Horton Hears a Who! (1990's)

Kirsten Dunst
as Mayor's Daughters in Horton Hears a Who! (1990's)

Tempestt Bledsoe
as Young Elphaba in Wicked (80s)

Dom DeLuise
as Spike Nolan in Brewster's Millions (1975)

Demond Wilson
as Montgomery Brewster in Brewster's Millions (1975)

Oliver Robins
as Little Boy in The Outsiders ('80s Genderswap/Genderbent)

Robert Guillaume
as Principal Garrison in Goosebumps (1995)

Johnny Depp
as Evan in The Outsiders ('90s Genderswap/Genderbent)

Todd Bosley
as Little Boy in The Outsiders ('90s Genderswap/Genderbent)

Alan Arkin
as General Volkova in Indiana Jones and the Heart of Yule (1991)

Chris Stapleton
as Time & Tide in The Plague Dogs
Jean Seberg
as Princess Fiona in Shrek (1971)
Cantinflas
as "Monsieur" Robin Hood in Shrek (1971)

Dan Aykroyd
as Orville in The Rescuers (1990s)

John Williams
as Composer in The Outsiders (1993)

Siedah Garrett
as Stay Gold in The Outsiders ('80s Genderswap/Genderbent)

Taylor Dayne
as Stay Gold in The Outsiders ('90s Genderswap/Genderbent)

Bryan Adams
as Lead The Way in Caddyshack (2000)
Mia Sara
as Marcia in The Outsiders (1993)

Michael Bolton
as Stay Gold in The Outsiders (1993)