10 Teen Movies That Are Smarter Than You Think

One of the defining teen movies of the '90s, Amy Heckerling’s Clueless features a whole host of then-up-and-coming stars, including Alicia Silverstone, Paul Rudd, Brittany Murphy, and Breckin Meyer. And it is the very opposite of what its title suggests.

Cher Horowitz (Silverstone) is the ditzy, popular, and well-meaning rich kid the film’s title refers to, who makes it her mission in life to look good, live well, and play matchmaker across her high school. She renegotiates her poor grades, sets teachers up on dates, shops ‘til she drops, and falls for her stepbrother Josh (Rudd).

Clueless is all tongue in cheek, a satire of the very culture it represents, showing the excesses and idiocies of the affluent, Hollywood-adjacent types for whom the tribulations of life are largely inconsequential. But it’s also a loose adaptation of Jane Austen's Emma, jettisoning the Surrey setting, the period aesthetic, and the 19th-century English diction in exchange for SoCal everything. And it well and truly does the job, adapting the book for modern audiences while launching a biting critique that lambasts Austen’s uncritical fascinations with status, matchmaking, and high society.