Josie Geller, a baby-faced junior copywriter at the Chicago Sun-Times, must pose as a student at her former high school to research contemporary teenage culture. With the help of her brother, Rob, Josie infiltrates the inner circle of the most popular clique on campus. But she hits a major snag in her investigation -- not to mention her own failed love life -- when she falls for her dreamy English teacher, Sam Coulson.
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
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
Maya McLaughlin
Lara
David Douglas
Rasta
Giuseppe Andrews
Denominator
Chali 2na
Ozomatli Band Member
Cut Chemist
Ozomatli Band Member
Will-Dog Abers
Ozomatli Band Member
Raul Pacheco
Ozomatli Band Member
Tara Skye
Tyke
Mark Allen
D.J.
Joe Ochman
Prom Judge #1
Don Snell
Prom Judge #2
Tinsley Grimes
Little Red Riding Hood
Amanda Wilmshurst
Fruit Headdress Woman
Ulises Bella
Ozomatli Band Member
William Marrufo
Ozomatli Band Member
James Hunter
Bully (uncredited)
Mike Stoklasa
Man on Swing (uncredited)
Rich Evans
Man with Balloon (uncredited)
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