Clueless and the art of an openhearted outlier

HOW DO YOU MEASURE THE WORTH OF A FILMMAKER’S career? Do you tick off box-office returns, or the awards lined up on a shelf? Which is a better determination of success, a string of hits or a film that lives on in the cultural imagination for decades, and counting?

- BY STEPHANIE ZACHAREK

Or how about this: Can you measure a career in terms of generosity of spirit?

Writer-director Amy Heckerling’s Clueless turns 30 this summer, and if she’d made no other movies, this delightful modern reimagining of Jane Austen’s Emma would have been an accomplishment by itself. Alicia Silverstone’s Cher, a Beverly Hills high school student with a closet of riotous and costly mix-and-match outfits and a knack for negotiating higher grades without actually earning them, comes off as shallow and spoiled. But there’s kindness and decency there too: she tries her hand at matchmaking, at first to further her own aims, only to realize that she likes bringing people together. She’s too pragmatic to want love for herself, until she’s forced to acknowledge that she’s fallen for the guy she’d always thought of as an annoying brother figure, Paul Rudd’s Josh, the son of her father’s ex-wife.

Clueless is both original (credit Heckerling with bringing the phrase As if! into the lexicon) and expertly crafted (its smart, breezy gags are strung together as gracefully as a strand of pearls). It also shows great affection for its characters, even while mocking them gently. When Cher refers to one of the great sword-and-sandal epics as “Sporadicus,” you love her more, not less: she’s not demeaning movies and experiences that are unfamiliar to her—she’s just so eager that she bungles some of the specifics.

That’s the Heckerling touch, the mark of a filmmaker who has always led with confidence rather than ego— which is why the industry, incapable of grasping the difference between the two, never knew what to make of her, not even after she’d made one of the greatest teen movies of the 1980s, if not all time, 1982’s Fast Times at Ridgemont High. Maybe it takes an outlier to make comedies that endure, as Clueless and