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This edgy comedy follows the romantic travails of a disillusioned record store owner in Chicago during the course of his latest break-up. He mulls over his "top-five" break-ups searching for the key to things, re-evaluating his life, even as his life comes apart at the seams. Revisiting the former girlfriends seems like a way to expiate his past, so he embarks on a series of revisitations, each revealing a different aspect of the past he had forgotten or misinterpreted. He finally reconciles his past, works things out with his current break up and gets back together, and realizes that he still has self-destructive urges....

The synopsis I have just provided doesn't sound like a recipe for hilarity, but as presented by the utterly deadpan John Cusack and by prickly director Stephen Frears, this movie cuts deep and provides some astonishingly funny scenes. For myself, a large part of its appeal stems from the shock of recognition. Having worked in the kind of millieu presented in the film, I recognized each and every character. Should the viewer wander into a record store of the type depicted here, he or she will discover that the movie isn't inventing anything that isn't already there for the taking. This casual reality serves to heighten the inner turmoil experienced by Cusack's character and places it in a context that is so absurd, it has to be true. The film itself is structured as a monologue, of sorts, with Cusack speaking directly with the audience, which enables the film to take side trips into the fantasy life of its narrator--most hilariously when he is confronted by his latest girlfriend's new boyfriend (a shallow, Yanni-esque "confrontation manager" played by Tim Robbins) and fantasizes about three separate responses to him, but also when he muses that his life is like a Bruce Springsteen song and Springsteen himself shows up to offer him advice. It is in these moments that the film transforms into one of the finest and most accutely observed comedies in recent memory. It is a pleasure to see that the Stephen Frears who directed My Beautiful Laundrette and The Grifters is still lurking about the fringes of cinema. This is his best film in eons and it isn't afraid to make the audience squirm. Cusack is up to the task: his character is sympathetic, but he isn't entirely likeable. He projects a kind of tired, edgy neurosis that immediately marks him as a real human being and not just a character to hang a movie on. The Academy ignored his role in Being John Malkovich; they will be hard pressed to ignore him here. Some of his girlfriends are remarkable, too, especially both Lily Taylor and Catherine Zeta-Jones (who almost redeem themselves for their participation in The Haunting). Perhaps the most striking thing about the movie is its restlessness. It never really finds a comfortable groove into which to drop the needle, and so keeps the audience on tenderhooks all the way through. It never settles into predictability.

The fall of 1999 was one of those magical periods in which good movies were not only being released, they were finding an audience. The first part of 2000 has been pretty bad, but with this movie and with Wonder Boys, touches of that magical autumn are beginning to reappear.