After discovering his high school crush can't date until her brash older sister does, a lovesick teen enlists a bad-boy classmate to woo her.
Heath Ledger
Patrick Verona
Julia Stiles
Katarina Stratford
Joseph Gordon-Levitt
Cameron James
Larisa Oleynik
Bianca Stratford
David Krumholtz
Michael Eckman
Andrew Keegan
Joey Donner