A pitch-perfect souvenir of the '90s, Clueless packaged the worst of teens with the best of Alicia Silverstone

Its star was the ”Aerosmith girl,” it had been stalled in development hell, and it opened on July 19, 1995 — the tail end of the antipop grunge era. Despite those drawbacks, Clueless — a candy-coated, slang-dropping look at Beverly Hills brats — raced to the head of the box office class and became a definitive relic of the prosperous Clinton era.

It also took writer-director Amy Heckerling back to school, the setting that first brought her acclaim in 1982 with Fast Times at Ridgemont High. This go-round, she explored the loopy world of ultrapopular Cher (newcomer Alicia Silverstone) and her best friend, Dionne (Stacey Dash). Using Jane Austen’s 1816 novel Emma as inspiration, Heckerling carved out a wafer-thin plot: While wearing outrageously expensive duds, the girls navigate the halls of Bronson Alcott High — where students proudly sport plastic-surgery bandages — and vow to give the frumpy Tai (Brittany Murphy) a makeover. ”Cher was someone who really saw the glass as half full,” says associate producer and Heckerling’s longtime friend Twink Caplan. ”That was the beauty of her, and that’s why everybody liked her.”

Sadly, not everybody liked the movie: Its original studio, Twentieth Century Fox, held it in turnaround for months. The wait was hard on Heckerling and her associates — ”[Fox] wanted it to be guys instead of girls,” huffs Caplan — until Uberproducer Scott Rudin read the script and took the film to Paramount.

Big budgets? High-priced actresses? As if! The film cost a modest $13 million, a figure achieved by not casting stars, but rather stars-in-the-making like Silverstone, an MTV staple thanks to her three Aerosmith videos. ”Other people could play that kind of a character,” says Heckerling, ”but she just embodied it.” Oscar buzz swirled around the then-18-year-old, but a nod never materialized. And despite the film’s strong legs — it grossed $56.6 million and even launched a TV series on ABC — Silverstone’s career plateaued, thanks to underwhelming follow-ups like 1997’s Batman & Robin and 1999’s Blast From the Past. Broadway has been kinder: She’s currently performing opposite Kathleen Turner in the stage version of 1967’s The Graduate.

Her costars have fared better, as once again Heckerling showed her Fast Times knack for uncovering budding talent, including Donald Faison (NBC’s Scrubs), Jeremy Sisto (HBO’s Six Feet Under), and Murphy (star of 2001’s Don’t Say a Word). ”You stick your foot in a different river every time,” says Heckerling. ”I was just really lucky those great people were out there.” Whatever.

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