Never Been Kissed (1999)

Synopsis
Many people wish they could go back to high school, knowing what they know as an adult; Josie Geller gets the chance to do just that in the comedy Never Been Kissed. Josie (played by Drew Barrymore) is a 25-year-old copy editor at a newspaper in Chicago. But it's her youthful looks as much as her journalistic skills that finally win her a writing assignment: she's ordered to enroll in high school posing as a teenager for a story on the state of America's youth. Trouble is, Josie was a hopeless nerd in high school (called "Josie Grossie" by her classmates); she had no idea of how to fit in with the cool kids, and she's hardly gotten any better at it in the seven years since graduation. While Josie makes fast friends with a bookish girl named Aldys (Leelee Sobieski), and also takes notice of her good-looking English teacher Mr. Coulson (Michael Vartan), she realizes for the sake of her story she has to infiltrate the cool girls' clique, which will be impossible without someone to give her a crash course in hipness. Josie's brother Rob (David Arquette), obviously the more style-conscious sibling, offers to sign up for the same school to act as the cool-guy friend she'll need to fit in, but just when Josie starts making headway (and starts enjoying high school for a change), her editor changes the focus of the story -- he now wants a feature on improper relations between teachers and students, which will not be good for her deepening friendship with Mr. Coulson. Never Been Kissed also features supporting performances from John C. Reilly, Molly Shannon and Jordan Ladd (the latter in a much more wholesome vehicle than her last cinematic visit to cinematic teen-town, Gregg Araki's Nowhere). ~ Mark Deming, All Movie Guide