Starring Alicia Silverstone, Stacey Dash, Paul Rudd, Brittany Murphy, Dan Hedaya

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Seminal teen comedy updating Jane Austen’s novel Emma, starring Alicia Silverstone as Cher, a wealthy, beautiful, spoiled high schooler who intervenes in the love lives of those she deems less fortunate before realizing she’s clueless. One of my favorite teen films. Successfully satirizes ’90s culture while also churning out a delightful romantic comedy.

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