One of my all-tine favorites (may contain spoilers)

Rating: Null/10 (30 August 2004)

This movie sums up a lot about failed relationships... especially about what it's like actually being the one who fails (i.e. gets dumped repeatedly).
John Cusack plays Rob Gordon, an introspective college dropout in his early-to-mid 30s who just barely gets by, running his own record store called "Championship Vinyl". One day his girlfriend leaves him, throwing his whole world in chaos. So he sits back, digs up old, painful memories and starts to wonder why he is "doomed to be left" - why he is always the one that gets dumped. He decides to get in touch with his "top five" ex-girlfriends ("those were the ones that really hurt") to find answers and of course he also tries to get his now-ex girlfriend to go back out with him. Unfortunately, she is already "otherwise involved". So much for most of the story - I won't give away the ending here though, that's for you to find out ;-)
To base a movie on a Nick Hornby novel, like this one, is surely a good place to start, depending of course on how well the novel is adapted to the big screen. In this case, it works quite well, although not-so-minor changes have been made. For one thing, the setting is downtown Chicago, and not London, as it was in the original novel.
The casting is well done. First of all, anyone who appreciates Jack Black's abundant acting talent will LOVE the way he plays his freaked-out, neurotic "Eric" character. John Cusack also does a good job in his lead role, especially in sad moments where you can really feel the pain in his character while he has that sinister, regretful look on his face.
The film really is entertaining and offers a couple of great laughs alongside a somewhat deep and serious storyline. Maybe it lacks some pace every now and then, but instead you are rewarded with a few thought-provoking dialogs on the nature of relationships and why people fail at them. It makes this movie even more worthwhile. In fact, the first time I watched it, it did much to comfort me during a time when MY girlfriend had just left me... **spoiler ahead!!!** in my case, however, I wasn't lucky enough to get a happy ending like John Cusack does at the end of the movie... bummer :-/
All in all: Absolutely recommended... not just for someone who likes to be deep in thoughts about relationships ;-)
8/10