Cher Horowitz (Alicia Silverstone) is an attractive, popular, and rich 16 year-old who is at the top of the high school social scene and is happy and self-assured in her fashion-obsessed world. She lives in a Beverly Hills mansion with her father Mel (Dan Hedaya), a ferocious $500-an-hour litigator. Her mother is long dead, having succumbed to complications while undergoing liposuction. Cher's best friend is Dionne (Stacey Dash), who is also rich, pretty, and hip, and understands what it's like to be envied. Among the few people to find much fault with Cher is Josh (Paul Rudd), her intellectual ex-stepbrother who visits during a break from college. Josh and Cher argue continually but without malice. She refers to him as "granola breath" and mocks his altruistic idealism, while he teases her for being selfish, vain, and superficial, and says her only direction in life is "toward the mall".
This makes Cher want to prove that she has a social conscience. First, she plays matchmaker for two lonely, nerdy, hard-grading teachers, Mr. Wendell Hall (Wallace Shawn) and Miss Toby Geist (Twink Caplan). She achieves her original goal of making them relax their grading standards so she can renegotiate a bad report card. But when she sees their new-found happiness she realizes she likes doing good deeds. Cher now decides that the ultimate way she can give back to the community would be to "adopt" a "tragically unhip" new girl at school, Tai Frasier (Brittany Murphy). Cher and Dionne give Tai a makeover and make her popular. Cher also tries to extinguish the strong mutual attraction between Tai and Travis (Breckin Meyer), an amiable skateboarding slacker, and to steer her toward Elton (Jeremy Sisto), a rich snob.
Her second matchmaking scheme backfires when Elton rejects Tai and makes a play for Cher. Matters worsen, however, when Cher's "project" works a bit too well and Tai's popularity begins to surpass Cher's, especially after Tai has a "near-death" adventure at the mall that helps to skyrocket her to fame at school. Other classmates, including Dionne and Cher's longtime rival classmate Amber (Elisa Donovan), soon gravitate toward Tai, and Cher finds herself demoted from queen to princess at high school. Meanwhile, Cher has a couple of romantic problems with boys at school. The first involves Elton, and the next is Christian (Justin Walker), a handsome classmate with great fashion sense who turns out to be gay. Cher naively and repeatedly fails to understand Christian's hints that he is gay, and tries unsuccessfully to seduce him while they are alone one night watching "Spartacus". The next day, Dionne's boyfriend Murray (Donald Faison), roaring with laughter, makes her mistake clear to her at last.
Events reach a crisis after Cher fails her driver's test and can't "renegotiate" the result. When Cher goes home, crushed, Tai confides that she's taken a fancy to Josh and wants Cher to help her get him. Cher says she doesn't think Josh is right for her, and they quarrel. Cher, left all alone, begins to think she has created a monster in her own image. Feeling "totally clueless", she reflects on her priorities and her repeated failures to understand or appreciate the people in her life. Most of all, she keeps thinking about Josh and Tai, and wonders why she cares so much.
After much soul-searching and a shopping spree to many Beverly Hills boutiques, Cher falls in love with Josh. She begins making awkward but sincere efforts to live a more useful life, even captaining the school's Pismo Beach disaster relief effort. A scene near the end of the film finds Cher and Josh stumbling over how to admit their mutual feelings for each other, finally culminating in a tender kiss on the steps of her father's mansion. The film has a happy ending. Cher's two nerdy teachers at school get married, her friendships with Tai and Dionne are reaffirmed, and Tai and Travis are in love. And Cher, in Josh's arms, has found love and meaning in her life.
This smart, funny, sweet, romantic, and hip movie is a classic teenage film. There is no gross-out humor or slapstick, and in many ways it defines the generation it portrays. It spun off a TV show and a series of books. An update of Jane Austen's 1816 novel "Emma", it's gently satirical, with a big heart, bright colours, and intentionally funny product placements. David Kitay composed the music score, and Amy Heckerling ("Fast Times at Ridgemont High") scripted and directed.
