Parker Posey as Priscilla Chase

Paul Rudd as Jack Chase

Mischa Barton as Kristen Taylor

Miranda Bailey as Sherri

Keith David as Coach Popovitch

Tim Russ as Douglas

Robert John Burke as Binky Taylor

Liza Minnelli as Alyssa Donahue

Danny DeVito as Wayne the Pool Guy

Winter Ave Zoli as The Water's Fine Girl

Adam Nelson as Kid at Vending Machine

Ramon Adams as Black Student

Jennifer Luu as Chinese Student

Alex Potapenko as Blonde Student

James Kisicki as Dr. Harry

Brynn Horrocks as Punky Chick

Richard A. Clark as Video Tech No. 1

Randall Harr as Video Tech No. 2

Christopher Mattingly as Nerd

Debrae Barenfeld as Receptionist

John Sloan as Guy at Club

Brandon Lewis as Black Hipster

Michael Orlando as Hispanic Man

J.E. Smith as Young Marine / English Guy

Toby Radloff as Toby

Ed Brigadier as Fridtjof Knudsen

Molly McGinnis as Woman No. 1

Bernard Canepari as Higher Up

Alexander Alioto as Waiter

Thomas T.K. Zung as Natty Chinese Man

Marisa Miller as Assistant Principal

Heather Graham as Justine

Fumi Desalu-Vold as Coach's Wife (uncredited)