Cast
- Drew Barrymore as Josie Geller, a 25-year-old copy editor who works for the Chicago Sun-Times.
- David Arquette as Rob Geller, Josie's younger brother.
- Michael Vartan as Sam Coulson, a young, attractive English teacher at the high school in which Josie enrolls.
- John C. Reilly as Augustus "Gus" Strauss, Josie's superior
- Leelee Sobieski as Aldys, one of Josie's only friends at the high school when she starts. She is considered by most of the popular people a "Math Geek."
- Jeremy Jordan as Guy Perkins, the most popular guy in school.
- Jordan Ladd, Jessica Alba, and Marley Shelton as Gibby, Kirsten, and Kristen, the three most popular girls in the school.
- Molly Shannon as Anita, Josie's friend who works with her at the paper.
- Other characters
- Denny Kirkwood as Billy Prince, Josie's crush in her first high school experience; he invited her to the prom, only to have brought another girl.
- Marissa Jaret Winokur as Sheila, Josie's best friend in her first high school experience.
- Maya McLaughlin as Lara, Sam's uptight girlfriend.
- Giuseppe Andrews as Denominator
- Branden Williams and James Edward Franco as Tommy and Jason, two of Guy's friends.
- Octavia L. Spencer as Cynthia
- Cress Williams as George
- Garry Marshall as Rigfort
- Sean Whalen as Merkin
- Martha Hackett as Mrs. Knox
- Jenny Bicks as Miss Haskell
- Katie Lansdale as Tracy
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