High Fidelity (2000)

Rob Gordon has excellent material for a late-night music conversation and a worrying ability to make every subject loop back to his romantic grievances. His top-five-breakup audit turns other people into supporting evidence in the case of Poor Rob. The film knows he needs to grow up; the joke is not that caring about records makes someone difficult. It is that ranking feelings is much easier for him than listening to the people having them.