Jack Chase

Paul Rudd

Priscilla Chase

Parker Posey

Kristen Taylor

Mischa Barton

Wayne the Pool Guy

Danny DeVito

Sherri

Miranda Bailey

Alyssa Donahue

Liza Minnelli

Coach Popovitch

Keith David

Douglas

Tim Russ

Binky Bartlett

Robert John Burke

Fridtjof Knudsen

Ed Brigadier

Justine

Heather Graham

Dr. Harry

James Kisicki

Girl `The Water's Fine'

Winter Ave Zoli

Kid at Vending Machine

Adam Nelson

Guy at Club

John Sloan

Punky Chick

Brynn Horrocks

Black Student

Ramon Adams

Chinese Student

Jennifer Luu

Blonde Student

Alex Potapenko

Toby

Toby Radloff

Assistant Principal

Marisa Miller

Video Tech No. 1

Richard A. Clark

Video Tech No. 2

Randall Harr

Coach's Wife (uncredited)

Fumi Desalu-Vold

Nerd

Christopher Mattingly

Receptionist

Debrae Barenfeld

Black Hipster

Brandon Lewis

Hispanic Man

Michael Orlando

Black Hipster

Brandon J. Lewis

Young Marine/English Guy

James E. Smith

Woman No. 1

Molly McGinnis

Higher Up

Bernard Canepari

Waiter

Alexander Alioto

Natty Chinese Man

Thomas T.K. Zung

Coach's Wife

Fumi Desalu

Video Store Clerk

Logan Mackey

Restaurant Patron

Victoria Von Dannenberg