I wonder how much control John Cusack has on his movies. They're almost always a bit odd.
This one uses monologues to the camera. There's quite a bit of exposition this way. Also, several of the characters used "Top 5" lists on all kinds of subjects. And they'd rate each other's lists. Whenever they're doing the other Top 5's you think you might have an idea where they're going, then they start pulling out really obscure references and they defend/explain their choices. It's interesting, in a geeky sort of way. I don't remember most of the lists, but the main one that ran through the movie was Top 5 Breakups by Cusack's character.
Cusack plays a record store owner and part-time DJ. If I remember rightly, the record store was classic records, only. At one point a middle-aged man comes in to buy a record for his daughter and one of the clerks (from Tenacious D?) chases him out. Basically, just like an self-righteous uber-geek who can't stand that other people don't know as much about classic music as he does. Maybe like a baseball stats-hound who looks down his nose at anyone who can't name off a Yankee player for every number.
So the story revolves around Cusack's latest breakup and how he can get back together with her. Meanwhile, he's attracted to a new girl he just met. Plus, he's trying to get closure on his past Top 5 breakups.
On my brother's Total Movie Value Scale, Rental with Dinner. Another odd and generally fun Cusack movie, but it doesn't stick as well as some of his others.
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