Even though there was a lot of music mentioned in the film that I'm not really familiar with, I'm one of those people that has a ridiculously varied music collection, and I know a lot of bands no one's ever heard of or no one remembers, so I can identify with the 'great record collection reorganization' as a form of soothing comfort, making compliation tapes for people, stuff like that. I also know the feeling of imaginary superiority that having such an encyclopedic knowledge of obscure music can give you. It just makes you feel cooler to know that the music YOU like is the cool stuff, and everyone else who listens to top 40 stuff is just ignorant. It's complete horseshit, because musical tastes vary so widely, and as hard as it is to admit, popular music has its charm as well, and if people enjoy it (even if it IS immensely stupid crap with insipid lyrics, mundane instrumentation and cookie-cutter pretty people lip synching to it)... well, it's hard to begrudge them their tastes. Well, no, actually, it's easy to begrudge them - it's just hard to justify it without coming off like a snobby elitist bastard.

Anyway, the story centers around music geek and record shop owner Rob Gordon (John Cusack) and his dealings with the breakup of his relationship with Laura (Iben Hjejle) and with the antics of his cronies - music elitist bastard Barry (Tenacious D's Jack Black) and the unassuming Dick (Todd Louiso). Rob is far from the flawless romantic comedy hero - he's a neurotic, self-absorbed guy, completely messed up by his frustrating dating history. So, when the crushing news is delivered that Laura ran off with the moron neighbor from upstairs named Ian (Tim Robbins), he goes on a quest to find out why the top five most devastating breakups of his life happened, to try and put an end to some of his neuroses... and help figure out what to do with his life.

Aside from being set in Chicago in the year 2000 rather than London in the early 90s, the film remains surprisingly faithful to the novel it's based on. The funny monologues are preserved through the handy trick of talking to the camera, although there are some funny bits that were needlessly left out. I don't think I've ever seen John Cusack give a bad performance, and when Joan is along for the ride, it usually equals good stuff. Hjejle is a little iffy, not quite appearing to have the appropriate emotional range... but she's adequate. Jack Black is great, as always. Hilarious and insane. Long Live Tenacious D. Louiso is also funny as the mousy, nervous Dick. Catherine Zeta-Jones is on her way to redeeming herself from crap like The Haunting by playing a pretty good Charlie - one of the ex-girlfriends Rob is tortured by, although they didn't dwell quite enough on how MUCH Charlie screwed Rob up. It's also good to see Lisa Bonet back around - long live the Huxtables! She's pretty damn foxy in this film, too.

It's a funny film, with a lot more subtle humor and cynical emotional observations than in your standard relationship movie, although I have a feeling that reading the book first might have contributed to my higher opinion of it.

One thing that's sorta sad to note is that John Cusack is now old enough to need to have someone else play him as a teenager.