Outside Providence

Outside Providence is a 1999 coming-of-age comedy about Tim Dunphy, a pot-smoking slacker whose blue-collar father ships him off to a Connecticut prep school after a run-in with the police, where he falls for a classmate named Jane. Amy Smart is the only celebrity on the site from this one, and the archive holds a single scene of her. Keep expectations in check: it is a romance-comedy, so the clip is on the sexy side rather than a full sex scene. One scene, one actress, and that is the whole entry.