1. Amanda Bynes as Viola/Sebastian
Fun fact: Filmmakers originally wanted to cast Jesse McCartney to play Viola's brother Sebastian because they thought he and Amanda resembled each other.
2. Channing Tatum as Duke
Fun fact: Channing did his own bicycle kicks during the soccer scenes.
3. Robert Hoffman as Justin
Fun fact: In 2006, Robert was also the star of the popular YouTube video "Urban Ninja."
4. Brandon Jay McLaren as Toby
Fun fact: Brandon played the Red Ranger in 2005's Power Rangers S.P.D.
5. Alexandra Breckenridge as Monique
Fun fact: Alex is married to Casey Hooper, the lead guitarist for Katy Perry.
6. David Cross as Principal Gold
Fun fact: During filming, David Cross willingly took on several tasks on set, including window washing and lawn mowing.
7. Laura Ramsey as Olivia
Fun fact: Both Laura and Alex went home covered in bruises after filming the epic bathroom fight scene.
8. Jonathan Sadowski as Paul
Fun fact: Jonathan currently stars in the Freeform sitcom Young & Hungry, about a wealthy entrepreneur and his personal chef.
9. Vinnie Jones as Coach Dinklage
Fun Fact: Vinnie is actually a former professional footballer who played midfielder from 1984 to 1999 for several teams, including Wimbledon, Leeds, and Chelsea.
10. Emily Perkins as Eunice
Fun fact: The role of Eunice was initially very small, but because Emily nailed it at the read-through, the director asked for her character to be given more lines.