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Clueless (1995)
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Cher's narration is so breezily confident that the gap between what she believes and what the scene shows can slip past on a first viewing. Amy Heckerling packs the clothes, school politics and supporting reactions with comic information. Come back once the romance is familiar and enjoy how precisely the film lets its heroine misunderstand a world she thinks she has organised.
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About Clueless
Shallow, rich and socially successful Cher is at the top of her Beverly Hills high school's pecking scale. Seeing herself as a matchmaker, Cher first coaxes two teachers into dating each other. Emboldened by her success, she decides to give hopelessly klutzy new student Tai a makeover. When Tai becomes more popular than she is, Cher realizes that her disapproving ex-stepbrother was right about how misguided she was -- and falls for him.