Jamie Bell
Dean
Camilla Belle
Crystal
Justin Chatwin
Billy
Glenn Close
Carrie Johnson
Kathi Copeland
Parent #1
Rory Culkin
Charlie Stiffle
Thomas Curtis
Charlie Bratley
Tim DeKay
Mr Peck
Lauren Holly
Boutique Owner
Carrie-Anne Moss
Jerri Falls
David Ellison
Student #1
William Fichtner
Mr. Bill Stiffle
Ralph Fiennes
Mayor Michael Ebbs
Richard Gleason
Parent #2
Caroline Goodall
Mrs. Parker
John Heard
Officer Lou Bratley
Susan Hegarty
Aide to Mayor Ebbs
Jason Isaacs
Mr. Parker
Allison Janney
Allie Stiffle
Josh Janowicz
Troy
Eric Jungmann
Student #2
Jeffrey Vincent Parise
Aide to Mayor Ebbs
Lou Taylor Pucci
Lee
Laura Shanahan
Party Goer #1
Scott Spiro
Party Goer #2
Max Van Ville
Student #3
Rita Wilson
Terri Bratley
Rachel Zeskind
Witness (uncredited)