High Fidelity is another of my all time favorite. John Cusack excels at brooding philosophical monologs loaded with sarcastic humor, and this movie really makes him shine.
He plays a sort of half-decent asshole which he admits being. However, the jokes and the situation makes it hard to see and kind of love him, which in turn enables you to really appreciate the whole story.
The characters are well played, Jack Black is his exuberant early self, and even the other sales clerk provides us with a lovable quiet self-effaced persona (a great balance to Cusack and Black). John Cusack himself is great, if a tiny bit over the top (which makes the movie, I must say), and his sister, Joan, is particularly well casted.
The dialogs are near perfect, the montage is without reproach (I especially like the one live mental alternate possibilities), and the soundtrack amazing.
See it, especially if you like lots of smart text.