Gil Junger Teacher Director, Actor Heath Ledger Patrick 'Pat' Verona Actor Julia Stiles Katarina 'Kat' Stratford Actor Joseph Gordon-Levitt Cameron James Actor Larisa Oleynik Bianca Stratford Actor David Krumholtz Michael Eckman Actor Andrew Keegan Joey Donner Actor Susan May Pratt Mandella Actor Gabrielle Union Chastity Actor Larry Miller Mr. Walter Stratford Actor Daryl "Chill" Mitchell Mr. Morgan Actor Allison Janney Ms. Perky Actor David Leisure Mr. Chapin Actor Cameron Fraser Trevor Actor Eric Riedmann Audio Visual Guy Actor Quinn Maixner Beautiful Jock Actor Demegio Kimbrough Coffee Kid #1 Actor Todd Butler Coffee Kid #2 Actor Dennis Mosley Cohort Actor Nick Vukelic Drugged Out Loser Actor Bianca Kajlich Coffee Girl Actor Ben Laurance Wimpy Loser Actor Aidan Kennedy Laughing Loser Actor Jesse Dyer Screaming Loser Actor Jelani Quinn Crying Loser Actor Joshua Thorpe Jock Actor Terence Heuston Derek Actor Alisa Mackay Coffee Girl #2 Actor Karen McCullah Writer Kirsten Smith Writer Jeffrey Chernov Executive Producer Jody Hedien Co-Producer Seth Jaret Executive Producer Andrew Lazar Producer Greg Silverman Associate Producer George Clinton Original Music Janet English Original Music Richard Gibbs Original Music Ralph Sall Original Music Joan Jett Non-Original Music Nick Lowe Non-Original Music Mark Irwin Cinematographer O. Nicholas Brown Film Editing Carol Winstead Wood Production Design Gilbert Wong Art Director Charles Graffeo Set Decoration Kimberly A. Tillman Costume Design Gail Goldberg Casting