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

Armand Reiser 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

Mark Edwards as School Guard #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)