But with the help of her brother Rob (Arquette), who enrolls to help her out, she befriends the cool kids, putting herself in a different social hierarchy this time around. When undercover reporter Josie Geller (Barrymore) is assigned to research teenage culture, she enrolls as a student at her former high school and finds herself reliving her high school insecurities as though she'd never left. Yearbook superlative: Best first kiss with a stadium audience Quintessential teen moment: When Sam finds out that Josie loves him and runs to the baseball field, where she is waiting on the pitcher's mound for her first kiss. Cast: Drew Barrymore, Leelee Sobieski, David Arquetteīest quote: 'I'm not Josie Grossie anymore!'