Kate Bosworth as Courtney Docherty

Chris Evans as Judd

Paul Dano as Joel

Matt McCoy as Gary Docherty

Josh Peck as Slim

Billy Kay as Gil Weatherton

Jeff Fahey as Mack Weatherton

Lonnie Farmer as Principal

Christopher McCoy as Sam Docherty

Elizabeth Duff as Marilyn Docherty

Jamie Benti as Rocco

Mike Chiarello as Penn

Rusty De Wees as Dennis Brownbear

Elizabeth Owens as Mrs. Marsdon

Doug Barron as Stan

Edsel Hughes as Mr. Burns

Matthew Burnett as Mr. Grisham

Joe Dye as Billy

Zack McCormack as Cory

Luz Alexandra Ramos as Prosecutor (as Luz Alexandra)

Ted Pendleton as Judge

James Allen Bradley as Foreman (as Jim Bradley)

Micheline Auger as Receptionist

Gail O'Brien as Coffee Shop Patron

Ed Oakman as Coffee Shop Patron

Jim Aspden as Coffee Shop Patron

Steve J. Macklin as Machine Shop Worker

Chuck Battles as Attorney

Ilene Blackman as Attorney #2

Martha Middleton as Secretary

Janelle Faignant as State Fair Patron (uncredited)

Miriam Stark as Boston School Teacher (uncredited)