Jessica Simpson

Katie

Luke Wilson

Ben

Rachael Leigh Cook

Haley

Penelope Ann Miller

Debra

Andy Dick

Freddy

Larry Miller

Richard Connelly

Willie Nelson

Pap Paw

Penny Marshall

Bolo Executive

Drew Fuller

Billy

Piper Mackenzie Harris

Amber Perry

Ritchie Montgomery

Mr. Carruthers

Niki Spiridakos

Nikolina

Karen Y. McClain

Betty

Bill Jenkins

Mr. Perry

Paul Vogt

Floyd

Matty Cardarople

Mailroom Worker

Drew Waters

Stripper Cop #1

Edrick Browne

Stripper Cop #2

Ryan Dunn

Griswold

Julius Washington

Lobby Security

Eric Gipson

Window Washer

Sam Marshall

Kid #1

Ethan Marshall

Kid #2

Paul T. Taylor

Bald Guy

Preston Vanderslice

Kyle

Dan Braverman

Cab Driver

Kelvin Payton

Waiter

Paul Sampson

Ivan

Shirly Brener

Laura

Matthew Walker

Angry Priest (as Matt Walker)