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
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