High Fidelity (2000)

Rob, a record store owner and compulsive list maker, recounts his top five breakups, including the one in progress. The film centers on Rob Gordon, a self-confessed music geek, who after getting dumped by his girlfriend, decides to look up some of his old flames to figure out what he keeps doing wrong. Rob spends his days at his record store, Championship Vinyl, where he holds court over the customers and is supported by his friends Dick and Barry. He also develops a dislike for two shoplifting skateboarder teenagers, Vince and Justin. Rob eventually tries to win back his lost girlfriend Laura while starting his own record label.