Cusack has a complicated love life. He's just been dumped by longtime live-in girlfriend Laura (Iben Hjejle, a Danish actress in her one big American movie role). Cusack turns for comfort to lounge-soul singer Lisa Bonet, while trying to win Laura back. Naturally, she makes it as difficult and cumbersome as possible, although she is already tired of her current boyfriend, zen counselor Tim Robbins.
Cusack is depressed by his love life difficulties. He decides to look up his ex-girlfriends, to research why he has had a string of failed relationships. Among the exes are free spirited brunette goddess Catherine Zeta-Jones, and the less memorable Lili Taylor and Joelle Carter. Cusack's somewhat hostile platonic friend is played by his real-life sister Joan, whom John usually manages to find some role for.
How others will see it. This film is especially made for rock music geeks, who are most likely to catch the significance of the myriad rock 'n' roll references. Those who don't know Love's "Little Red Book" from The Velvet Underground's "Who Loves the Sun" will be left wondering, "What's that song? It's pretty good."
Those who are indifferent to rock and its various genres have something to enjoy as well: the relationships, as told from the male point of view. John Cusack confides to the camera, and his observations are both witty and telling. You won't learn much about the beauty of the male psyche. Instead, you hear amusing resentment (e.g., Joelle Carter won't go to third base), jealousy (e.g. a desire to assault Tim Robbins, probably latent from viewing The Shawshank Redemption), frustration (getting Laura back means traversing a maze of phone calls and brief meetings), and triumph (he sleeps the hottest Cosby daughter! Yes!!!)
How I felt about it. Cusack is having his mid-life crisis a few years early. He doesn't care that he has no money, or that vinyl records stores are the buggy whip industry of the 21st century. He does care that there is no chick in his bed at night, and he'd like to understand why.
The search is more futile than revealing. He lacks the insight to learn why he is eventually rejected. (Correct answer: it goes with the territory). He does learn, though, that however hot Catherine Zeta-Jones may be, she also becomes a pretentious bore once you close your eyes. Also, Lili Taylor is kind of pathetic. So maybe it's okay that they broke up with him. But he would like Laura back.