Clueless

Title: Clueless
Author/Director: Amy Heckerling
Cast: Alicia Silverstone (Cher), Stacey Dash (Dionne), Paul Rudd (Josh), Donald Faison (Murray), Elisa Donovan (Amber), Breckin Myer (Travis), Jeremy Sisto (Elton), Dan Hedaya (Mr. Horowitz), Wallace Shawn (Mr. Hall), Twink Caplan (Miss Geist), Brittany Murphy (Tai).
ASIN: B00001MXXE (DVD)

Plot Summary: Cher Horowitz, a rich, spoiled Beverly Hills teen, enjoys shopping, hanging out with her friend Dionne, and playing matchmaker to all the people in her life. However, she's not as good at it as she thinks. Although Cher successfully matches two of her teachers together, when she tries to get Tai, the new girl in town, together with Elton, an obnoxious rich kid with a famous father, she finds out too late that Elton is interested in her instead, and Tai only has eyes for Travis, a good-hearted if slightly dim slacker. When Cher tries to pick out a love interest for herself, Christian, the object of her affections, turns out not to be as interested in her - or in her gender - as she had hoped. Throughout Cher's matchmaking misadventures, Josh, her ex-stepbrother who is living with Cher and her lawyer father, provides sardonic commentary, often provoking Cher into arguments in the process. However, it is not until Tai sets her sights on Josh that Cher realizes two things: first, that she has less of a clue than she thought about matchmaking, and second, that she may not hate Josh so much after all.