Ira and the movie Fast, Cheap & Out of Control. Advertised as wacky, it is anything but.
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A high school student named Rebecca tells the story of a friend of hers who changed over the course of four years from a preppy alternative kid to a member of the Latina clique to a ghetto girl to a Clueless girl (a girl who models herself after the girls in the film and TV show Clueless). It's hard to imagine many boys changing style this quickly, this willfully, this many times.