Drew Barrymore

Josie Geller

David Arquette

Rob Geller

Molly Shannon

Anita

Michael Vartan

Sam Coulson

Jessica Alba

Kirsten

John C. Reilly

Gus Strauss

James Franco

Jason

Octavia Spencer

Cynthia

Jenny Bicks

Miss Haskell

Garry Marshall

Rigfort

Sean Whalen

Merkin

Cress Williams

George

Sarah DeVincentis

Rhoda

Allen Covert

Roger in Op-Ed

Armand Reiser

Dutton

David Doty

Hairplug Bruns

Derek Morgan

Armcast Henson

Kathleen Marshall

Sun-Times Worker

Leelee Sobieski

Aldys

Marley Shelton

Kristin

Jordan Ladd

Gibby

Jeremy Jordan

Guy Perkins

Jason Weissbrod

Big Bad Wolf

Katie Lansdale

Tracy

Branden Williams

Tommy

Gregory Sporleder

Coach Romano

Martha Hackett

Mrs. Knox

Jennifer Parsons

P.E. Teacher

Andrew Wilson

School Guard

Alex Solowitz

Brett

Niesha Trout

Sera

Chad Haywood

Matz

Cory Hardrict

Packer

Chad Todhunter

Stoner #1

Daniel Louis Rivas

Stoner #2

Denny Kirkwood

Billy Prince

Marissa Jaret Winokur

Sheila

Carmen Llywelyn

Rob’s Girlfriend

Sara Downing

Billy’s Prom Date

Mike Moyer

Monty Malik

David Douglas

Rasta

Giuseppe Andrews

Denominator

Chali 2na

Ozomatli Band Member

Cut Chemist

Ozomatli Band Member

Joe Ochman

Prom Judge #1

Don Snell

Prom Judge #2

James Hunter

Bully (uncredited)

Mike Stoklasa

Man on Swing (uncredited)

Rich Evans

Man with Balloon (uncredited)