This film contains plenty of people we all know. They're called "losers." It is fairly common that an auteur of some sort, be it filmmaker or writer, will attempt to transform these losers into some other form of life by making them the subject of a story. Consequently, the audience is supposed to identify with the loser's feelings.
Director Stephen Frears does this with Rob (John Cusack) in a rather underhanded way. First, Cusack is dirty and dressed-down, which is a reminder that if he'd just take a bath and buy some new clothes, he would be neither of these things. The second is that Rob is surrounded with even bigger losers. Rob owns a failing music store and his two employees are Dick (Todd Louiso) and Barry (Jack Black), two people Rob refers to as "the musical moron twins." While all three of them are twenty or thirtysomethings working for minimum wage, at least Rob owns the store. Dick and Barry are just lesser versions of Rob in that they are social failures in addition to being financial ones.
The film pulls this "Ferris Bueller's Day Off" thing whereby Rob talks to the camera, which is done so that we easily discover what a self-serving prick he is. Having just broken up with Laura (Iben Hjejle) he begins recounting the tragedy of his romantic life, or as he likes to put it, his "top five break-ups." They include some girl when he was eight, Charlie (Catherine Zeta-Jones), Sarah (Lili Taylor), Penny (Joelle Carter) and, of course, Laura.
The film's course, which is hardly a mystery, is for Rob to discover the complicity of his own attitudes in leading to the current state of his life. Rob is insecure and selfish and has sort of given up taking risks in life. What I wanted to know was how in the hell such a guy could end up with all these great women. How exactly does that work?
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