5. Clueless (1995)
Director: Amy Heckerling
Starring: Alicia Silverstone, Brittany Murphy and Paul Rudd
Rated: PG-13
In this coming-of-age romantic comedy, Cher (Silverstone) is a high school student in Beverly Hills who must survive the challenges of adolescent life. When a new girl, Tai (Brittany Murphy) comes to town, Cher tries to boost her popularity, but doesn’t anticipate Tai falling for Cher’s kind-of-step-brother Josh (Rudd).
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