Rob Gordon (Jon Cusack) asks the audience, “Do I listen to pop music because I was miserable, or am I miserable because I listen to pop music?” Rob spends more time talking to us than he does to any of the other characters in the movie, which is part of the problem. His candor and charm, both considerable, have allowed him to carry his adolescence through his 20’s, and he is much more comfortable concocting the definitive list of the best side-one, track-one songs ever than he is thinking about, say the definitive list of worthwhile things to do with his life. As his girlfriend Laura (Iben Hjejle) moves out of his apartment, he begins to think that maybe it isn’t enough just to like the right stuff. Maybe what matters is what you are like, not just what you do like.
Rob owns the least commercial enterprise possible, a vintage record store called “Classic Vinyl.” Only the two hopeless guys who work for him (Jack Black and Jerry Maguire’s Todd Luiso — both superb) make him feel like a grown-up by comparison. They sit around all day, getting rid of potential customers who are just not cool enough to be allowed to buy their records, endlessly ranking everything in the world and seeing the whole world as one big chance to measure everything. The death of one character prompts them to devise a “top five songs about death” list. They hyper-critically rate everything except for their own sorry lives.
Laura’s departure of course prompts Rob to make a list of his five worst break-ups, which allows him to comfort himself that she is not even on the list. But as he tracks down the five on the list to see if he can figure out what went wrong, he begins to admit to himself that he is deeply wounded, and not just because he feels threatened and competitive at the thought of her new love interest (a hilarious cameo by Tim Robbins). He has to allow himself to understand that “fantasies always seem really great because there aren’t any problems,” but that he needs to move on to reality. And he has to allow himself to be a little less self-obsessed. He realizes that he just might be on someone else’s list of the five worst heart-breaks and that it is actually not very likely that a music superstar will show up to give him advice. Fortunately, the “professional appreciator” is wise enough to see how special Laura is, and that he can not just “create a sketch of a decent, sensitive guy;” he can actually become one.
Parents should know that this movie has very strong R-rated material, including explicit sexual references and sex for reasons other than intimacy (one-night stand just for the sex, sex to numb sad feelings). Characters drink and smoke a lot. Parents whose teens see this movie might want to see it, too, to talk with them about the way people change as they grow up.
Families who enjoy this movie will also enjoy some of Cusack’s other performances, including Say Anything and The Sure Thing.