Suggestions by @timemachine
8,267 suggestions
Larisa Oleynik
as Roxy in Winx Club (1999)
Sarah Michelle Gellar
as Stella in Winx Club (1999)
Rachael Leigh Cook
as Tecna in Winx Club (1999)
Nicole Bilderback
as Musa in Winx Club (1999)
Gabrielle Union
as Aisha/Layla in Winx Club (1999)
Jessica Alba
as Flora in Winx Club (1999)
Nikki Cox
as Bloom in Winx Club (1999)
Chad Michael Murray
as The Bad Boy in No Context/Typical 2000s Teen Comedy/Coming-of-Age Movie
Christina Ricci
as The Teacher in No Context/Typical 2000s Teen Comedy/Coming-of-Age Movie
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)