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Clueless (1995)
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Cher's matchmaking and social improvements keep going wrong in ways that are both ridiculous and recognisably well-intentioned. The bright clothes and quick dialogue are a delight, but her willingness to learn gives the comedy its good nature. It is a sunnier way to spend time with imperfection than another film about people being relentlessly awful.
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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.