- Amanda Bynes as Viola Hastings, a talented soccer player underestimated for being a girl, who dresses up as her fraternal twin brother Sebastian to play soccer at Illyria
- Channing Tatum as Duke Orsino, the soccer team captain, who is in love with Olivia and, later, with Viola
- Laura Ramsey as Olivia Lennox, a smart girl who falls in love with Sebastian (Viola)
- Vinnie Jones as Coach Dinklage
- Julie Hagerty as Daphne Hastings, the mother of Viola and Sebastian
- David Cross as Principal Horatio Gold
- Jonathan Sadowski as Paul Antonio, Viola's best friend and hair stylist
- Robert Hoffman as Justin Drayton, Viola's ex-boyfriend and Duke's rival
- Robert Torti as Coach Pistonek
- James Snyder as Malcolm Festes, the school nerd and Sebastian's (Viola's) rival. He owns a pet spider Malvolio.
- Alex Breckenridge as Monique Valentine, Sebastian's superficial girlfriend
- Amanda Crew as Kia, one of Viola's friends
- Jessica Lucas as Yvonne, one of Viola's friends
- James Kirk as Sebastian Hastings, Viola's fraternal twin brother, who is in Europe with his band.
- Emily Perkins as Eunice Bates, the nerdy and eccentric classmate with weird sexual fantasies
- John Pyper-Ferguson as Roger Hastings, the father of Viola and Sebastian
- Brandon Jay McLaren as Toby, one of Duke's best friends, who is attracted to Eunice
- Clifton Murray as Andrew, one of Duke's best friends
- Lynda Boyd as Cheryl, the debutante ball's hostess
- Katie Stuart as Maria, Olivia's friend
- Mark Acheson as Groundskeeper
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