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

Drew Waters as Stripper Cop #1

Edrick Browne as Stripper Cop #2

Ryan Dunn as Griswold

Julius Washington as Lobby Security

Eric Gipson as Window Washer

Sam Marshall as Kid #1

Ethan Marshall as Kid #2

Paul T. Taylor as Bald Guy

Preston Vanderslice as Kyle

Dan Braverman as Cab Driver

Kelvin Payton as Waiter

Paul Sampson as Ivan

Shirly Brener as Laura