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Slide 17 of 28

Clueless (1995)

Loosely based on Jane Austen's Emma, Alicia Silverstone stars in this one as Cher, a spoiled Beverly Hills princess with a passion for fashion and meddling in the love lives of others. When "tragically unhip" new girl Tai (played by Brittany Murphy) arrives at Bronson Alcott High School, Cher decides to take her under her wing and find her a boyfriend — but unfortunately, the guy who catches Tai's eye just so happens to be the guy Cher has secretly been in love with forever.

Image Source: Everett Collection