Drew Barrymore

as Josie Geller

David Arquette

as Rob Geller

Molly Shannon

as Anita

Michael Vartan

as Sam Coulson

Jessica Alba

as Kirsten

John C. Reilly

as Gus Strauss

James Franco

as Jason

Octavia Spencer

as Cynthia

Jenny Bicks

as Miss Haskell

Garry Marshall

as Rigfort

Sean Whalen

as Merkin

Cress Williams

as George

Sarah DeVincentis

as Rhoda

Allen Covert

as Roger in Op-Ed

Eduard Reese

as Dutton

David Doty

as Hairplug Bruns

Derek Morgan

as Armcast Henson

Kathleen Marshall

as Sun-Times Worker

Leelee Sobieski

as Aldys

Marley Shelton

as Kristin

Jordan Ladd

as Gibby

Jeremy Jordan

as Guy Perkins

Jason Weissbrod

as Big Bad Wolf

Katie Lansdale

as Tracy

Branden Williams

as Tommy

Gregory Sporleder

as Coach Romano

Martha Hackett

as Mrs. Knox

Jennifer Parsons

as P.E. Teacher

Andrew Wilson

as School Guard

Alex Solowitz

as Brett

Niesha Trout

as Sera

Chad Haywood

as Matz

Cory Hardrict

as Packer

Chad Todhunter

as Stoner #1

Daniel Louis Rivas

as Stoner #2

Denny Kirkwood

as Billy Prince

Marissa Jaret Winokur

as Sheila

Carmen Llywelyn

as Rob’s Girlfriend

Sara Downing

as Billy’s Prom Date

Mike Moyer

as Monty Malik

Steven Wilde

as Bouncer

Maya McLaughlin

as Lara

David Douglas

as Rasta

Russell Bobbitt

as Carny

Giuseppe Andrews

as Denominator

Chali 2na

as Ozomatli Band Member

Cut Chemist

as Ozomatli Band Member

Will-Dog Abers

as Ozomatli Band Member

Asdru Sierra

as Ozomatli Band Member

Raul Pacheco

as Ozomatli Band Member

Tara Skye

as Tyke

Mark Allen

as D.J.

Joe Ochman

as Prom Judge #1

Don Snell

as Prom Judge #2

Tinsley Grimes

as Little Red Riding Hood

Amanda Wilmshurst

as Fruit Headdress Woman

Ulises Bella

as Ozomatli Band Member

William Marrufo

as Ozomatli Band Member

James Hunter

as Bully (uncredited)

Mike Stoklasa

as Man on Swing (uncredited)

Rich Evans

as Man with Balloon (uncredited)