Clueless (Whatever! Edition)

Jane Austen might never have imagined that her 1816 novel Emma could be turned into a fresh and satirical look at ultra-rich teenagers in a Beverly Hills high school. Cher (Alicia Silverstone) and Dionne (Stacey Dash), both named after "great singers of the past that now do infomercials," are pampered upper-class girls who care less about getting good grades than wearing the right clothes and being as popular as possible. But Cher, who lives with her tough yet warm-hearted lawyer dad (Dan Hedaya) and hunky, sensitive stepbrother (Paul Rudd), also has an innate urge to help those less fortunate — like the two introverted teachers she brings together ("negotiating" herself improved grades in the process) and new friend Tai (Brittany Murphy), who starts out a geek and ends up a Cher prodigy. Cher also possesses her own sensitive side, and she is looking for the perfect boyfriend, whom she ends up finding where she least expected.

Alicia Silverstone won everyone over with her portrayal of a Beverly Hills teen, Cher, whose penchant for helping others with their relationships and self-esteem is a cover for her own loneliness. Director Amy Heckerling (Fast Times at Ridgemont High) made a smart, funny variation on Jane Austen's novel Emma, sweetly romantic and gently satirical of 90210 social manners. The cast is unbeatable: Dan Hedaya as Cher's rock-solid dad, Wallace Shawn as a geeky teacher, Paul Rudd as the boy who has always been Cher's surrogate brother--and the true holder of her most secret wishes. --Tom Keogh

Alicia Silverstone won everyone over with her portrayal of a Beverly Hills teen, Cher, whose penchant for helping others with their relationships and self-esteem is a cover for her own loneliness. Director Amy Heckerling (Fast Times at Ridgemont High) made a smart, funny variation on Jane Austen's novel Emma, sweetly romantic and gently satirical of 90210 social manners. The cast is unbeatable: Dan Hedaya as Cher's rock-solid dad, Wallace Shawn as a geeky teacher, Paul Rudd as the boy who has always been Cher's surrogate brother--and the true holder of her most secret wishes. --Tom Keogh