Suggestions by @timemachine
8,238 suggestions
Blake Lively
as The Preppy, Popular Girl in No Context/Typical 2000s Teen Comedy/Coming-of-Age Movie
Adam Brody
as The Main Protagonist's Crush in No Context/Typical 2000s Teen Comedy/Coming-of-Age Movie
Amanda Bynes
as The Main Protagonist's Best Friend in No Context/Typical 2000s Teen Comedy/Coming-of-Age Movie
Michelle Trachtenberg
as The Main Protagonist in No Context/Typical 2000s Teen Comedy/Coming-of-Age Movie
Heath Ledger
as The Bad Boy in No Context/Typical 1990s Teen Comedy/Coming-of-Age Movie
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)