Amy Heckerling's Clueless famously relocated Jane Austen's 1815 novel Emma to the 1990s of cropped cardigans and sneaker-sized cell phones, but in retrospect, it plays more like a class-conscious spin on the teen comedies of the 1980s.
Cher Horowitz (a pitch-perfect Alicia Silverstone) narrates in wide-eyed, gum-chewing fashion as an upper-class 16-year-old whose thrills include fashion and makeovers. She describes the job of her widowed father, Mel (Dan Hedaya, whose gruffness prevents things from getting too frothy), as a "litigator," noting that "those are the scariest kinds of lawyers." She and her best friend, Dionne (Stacey Dash), share names with "famous singers of the past, who now do infomercials." Their friendship, she explains, comes from the fact that they know what it's like for people to be jealous of them.
Outside of her social circle, she has a college-age ex-stepbrother, Josh (future Ant-Man star Paul Rudd), whom she disdains for his do-gooder ways and shabby fashion sense. After she gets a ticket for driving without a license, though, she ropes him into co-piloting her excursions around Beverly Hills. When she gets a C in her debate class, she settles on her first makeover project. She'll convince disheveled Miss Geist (Twink Caplan) that Mr. Hall (Wallace Shawn) has a crush on her, spiff up her image, and then talk the smitten teacher into raising her grade.
Mr. Hall ends up raising everybody's grades, so she next sets her sights on Tai (Brittany Murphy), a New York transfer student with even shabbier fashion sense than Josh and Miss Geist. Cher and Dionne upgrade her image, but Tai remains taken with Travis (Breckin Meyer), a pot-smoking skateboarder who admires her drawing skills. Cher would prefer to match her up with entitled rich boy Elton (Jeremy Sisto), except he only has eyes for her.
At a party in the Valley, her plans backfire so spectacularly that she ends up stranded at a gas station where an armed mugger absconds with her purse before Josh swoops in to rescue her. As Tai's star starts to rise, hers starts to fall. Though some of her matchmaking pays off, she comes to the conclusion that she'd like a boyfriend of her own. However, high school boys—even sophisticated ones like Christian (Justin Walker), aka the "Ring-Ding Kid"—don't float her boat. But when she sets out to help some people who really need it, her fortunes start to change.
Clueless put Heckerling back on the map after the success of the Cameron Crowe-scripted Fast Times at Ridgemont High, made a star out of Silverstone (who was previously best known for a series of Aerosmith videos), and jump-started an Austen craze that would continue for years to come on screens both big and small, sometimes with the addition of zombies and other bizarre anachronisms, but Clueless remains the gold standard.
This 25th-anniversary edition comes with a full-length trivia game, which is sure to stump even the most dedicated devotees, and six featurettes and one tutorial originally included with the 2005 DVD. The lack of a commentary track is unfortunate, but this is otherwise highly recommended.