101 Funniest Screenplays

Having examined high school in the San Fernando Valley (Fast Times at Ridgemont High), writer-director Amy Heckerling came over the hill and did it again, this time among Beverly Hills rich kids of the 1990s. While Clueless traffics in a far more materialistic world than Fast Times, it proved no less a cultural touchstone. Ostensibly a story about a privileged girl who learns about herself via some match-making escapades, the film resonated largely due to its style, knowing wit and unique vocabulary, which Heckerling concocted from her own field research. The film’s most famous expression – “As if!” – became an instant part of the lexicon. If Heckerling did Clueless as a loose riff on Jane Austen’s novel Emma, she brought it to a lampoon-able world of nouveau riche excess and privilege, with a composed, slightly ditzy, and ultimately humbled protagonist named Cher Horowitz.