Cher Horowitz is a good-natured but superficial girl who is attractive, popular, and extremely wealthy. A few months shy of her sixteenth birthday, she has risen to the top of the high-school social scene, and is happy and self-assured in her insular, fashion-obsessed world. She lives in a Beverly Hills mansion with her father Mel (Dan Hedaya), a ferocious $500-an-hour litigator; her mother has long since died, having succumbed to complications while undergoing liposuction surgery. Cher's best friend is Dionne Davenport, 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, her socially conscious ex-stepbrother who visits during a break from college. Josh and Cher spar continually but without malice; she refers to him as "granola breath" and mocks his scruffy idealism, while he teases her for being selfish, vain, and superficial, and says that her only direction in life is "toward the mall." Illustrating that Cher's selfishness is usually innocent and relatively harmless, Cher plays matchmaker for two lonely, nerdy, hard-grading teachers, Mr. Hall and Miss Geist. She achieves her ostensible purpose—to make them relax their grading standards so she can renegotiate a bad report card—but when she sees their newfound happiness, she realizes she actually enjoys 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. Cher and Dionne give Tai a makeover and initiate her into the mysteries of popularity. Cher also tries to extinguish the strong mutual attraction between Tai and Travis Birkenstock, an amiable skateboarding slacker, and to steer her toward Elton, a rich snob whose father is a music-industry executive.
Her second matchmaking scheme backfires when Elton rejects Tai and makes a play for Cher. Matters worsen 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" misadventure at the mall that helps to skyrocket her to fame at school. Other classmates, including Dionne's and Cher's longtime rival Amber, soon gravitate toward Tai, and Cher finds herself demoted from queen to courtier at high school.
Events reach crisis stage after Cher fails her driver's test and can't "renegotiate" the result. When Cher returns 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 Tai, 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 (which includes a solo shopping spree around various Beverly Hills boutiques), Cher realizes she has fallen in love with Josh. She begins making awkward but sincere efforts to live a more purposeful 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 one another, culminating in a tender kiss on the stairs of her home. The film has a happy Hollywood ending for Cher: Mr. Hall and Miss Geist get married; her friendships with Tai and Dionne are reaffirmed and solidified; Tai and Travis are in love; and now, in Josh's arms, she too has finally found love.
- Alicia Silverstone as Cher Horowitz
- Stacey Dash as Dionne Davenport
- Brittany Murphy as Tai Frasier
- Paul Rudd as Josh Lucas
- Dan Hedaya as Mel Horowitz
- Elisa Donovan as Amber Mariens
- Justin Walker as Christian Stovitz