Rob, played by John Cusack, is a man in his thirties who runs a record shop and finds himself contemplating the passage of time as he reflects on past relationships. This doesn't even account for the two men who consistently disrupt his life – Dick (Todd Louiso) and Barry (Jack Black), longtime fixtures known for their particular musical tastes that often alienate customers. With this odd assortment of characters behind the counter and a declining enthusiasm for vinyl among shoppers, the business isn’t exactly booming! Rob's recent breakup with Laura (Iben Hjejle) has prompted him to consider whether she might have been "the one," though he admits he’s felt that way about many women since childhood. Cusack weaves together the present narrative with direct-to-camera moments and flashbacks of his unsuccessful attempts at romance. He portrays a sense of helplessness remarkably well, and his life seems to mirror the diverse music playing in his store, reflecting his fluctuating emotional state. Some situations are recognizable and humorous, as his romantic pursuits often follow predictable patterns that many will likely find painfully familiar. I’ve never been fond of Jack Black's performances, but here he manages to be excessively loud in a way that actually works, creating an effectively irritating character; this contrasts nicely with Louiso’s more reserved Dick, whose preference for indie music appealed to me (and other fans of Belle and Sebastian). It’s a thoughtfully paced and written exploration of a man grappling with self-doubt, and I believe it represents Cusack's most genuine performance yet.

Source on TMDB