Jessica Simpson as Katie

Luke Wilson as Ben

Rachael Leigh Cook as Haley

Penelope Ann Miller as Debra

Andy Dick as Freddy

Larry Miller as Richard Connelly

Willie Nelson as Pap Paw

Penny Marshall as Bolo Executive

Drew Fuller as Billy

Piper Mackenzie Harris as Amber Perry

Ritchie Montgomery as Mr. Carruthers

Niki Spiridakos as Nikolina

Karen Y. McClain as Betty

Bill Jenkins as Mr. Perry

Paul Vogt as Floyd

Matthew Cardarople as Mailroom Worker