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A man discovers that there's more to love than a good mixed tape in this dramatic comedy about music and relationships. Rob (John Cusack), an obsessive record collector in his mid-thirties, is struggling to reconcile his adolescent enthusiasm for pop music with adult responsibilities and a more mature outlook. He runs a record shop with his friends Barry (Jack Black) and Dick (Todd Louiso), who are known to drive away customers whose taste in music doesn't match their exacting standards -- which may have something to do with why the shop is losing money. But Rob's biggest problem is his failing relationship with Laura (Iben Hjejle), a lawyer who needs more out of the relationship than Rob is capable of giving. To Rob's horror, Laura starts dating Ian (Tim Robbins), his upstairs neighbor, known throughout the building for his long and noisy sex sessions. Rob, on the other hand, finds himself catching the attention of singer/songwriter Marie DeSalle (Lisa Bonet), as he tries to deal with his breakup by tracking down his previous ex-girlfriends and taking a fresh look at what he's been doing wrong.

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