8,293 suggestions
Lisa Kudrow
as The Teacher in No Context/Typical 1990s Teen Comedy/Coming-of-Age Movie
Tori Spelling
as The Preppy, Popular Girl in No Context/Typical 1990s Teen Comedy/Coming-of-Age Movie
Freddie Prinze Jr.
as The Main Protagonist's Crush in No Context/Typical 1990s Teen Comedy/Coming-of-Age Movie
Jessica Biel
as The Main Protagonist's Best Friend in No Context/Typical 1990s Teen Comedy/Coming-of-Age Movie
Brittany Murphy
as The Main Protagonist in No Context/Typical 1990s Teen Comedy/Coming-of-Age Movie
Lamont Bentley
as Murray Duvall in Clueless (Late '90s)
Bianca Lawson
as Dionne Davenport in Clueless (Late '90s)
Leonardo DiCaprio
as Elton Tiscia in Clueless (Late '90s)
James Van Der Beek
as Travis Birkenstock in Clueless (Late '90s)
Joseph Gordon-Levitt
as Christian Stovitz in Clueless (Late '90s)
Nikki Cox
as Amber Mariens in Clueless (Late '90s)
Freddie Prinze Jr.
as Josh Lucas in Clueless (Late '90s)
Jamie-Lynn Sigler
as Tai Frasier in Clueless (Late '90s)
Sarah Michelle Gellar
as Cher Horowitz in Clueless (Late '90s)
Chris Columbus
as Director in Winx Club (2000s live-action movie)
Taylor Lautner
as Justin in Total Drama Island (2000s live action movie)
Ron Lester
as Owen in Total Drama Island (2000s live action movie)
Sara Paxton
as Lindsay in Total Drama Island (2000s live action movie)
Vanessa Hudgens
as Katie in Total Drama Island (2000s live action movie)
Amber Riley
as Leshawna in Total Drama Island (2000s live action movie)
