In retrospect, the success of writer-director Amy Heckerling’s 1995 teen comedy Clueless shouldn’t have been that surprising. The movie was a Jane Austen riff, released at a time when movies and TV were going Austen-crazy. It was set among the fabulously wealthy, at the dawn of the Internet boom years. And it’s a smart, funny high-school movie, which isn’t all that common in any era. Yet Clueless took a while to come together, starting life as a TV pilot before Heckerling was encouraged to stretch the idea to feature-length. The project then continued to gather dust until producer Scott Rudin became its champion, ultimately landing the film at Paramount, home of MTV and Nickelodeon—whose promotion would help turn Clueless into a hit. The long process shaped what’s on the screen. Structurally, the movie feels like four sitcom episodes stitched together, which makes it more eventful and less gimmicky than most of the other ’90s teenpics. And Heckerling has said that the idea to use Austen’s novel Emma as a loose framework for the plot came to her late, allowing her a way to make her movie about blindered rich kids without showing them as irredeemably awful.
Some elements of Clueless do still raise an eyebrow, though. The heroine, played by Alicia Silverstone, appears every bit the entitled brat, as she judges her classmates based on their clothes while manipulating them to her own ends. The plot is all about Silverstone playing matchmaker for her friends, but every maneuver is primarily for her own benefit. Clueless is also very ’90s, in both its cultural signifiers (the film features not one but two performances by The Mighty Mighty Bosstones, plus a character who’s into neo-swing) and its jokes that are no longer really jokes (such as how it’s supposed to be funny that everyone has a cell phone, but not funny that some have pagers). And then there’s Paul Rudd, who plays Silverstone’s college-aged stepbrother, and throughout is meant to be emblematic of proto-hipster-douchebaggery, from his 688 Records T-shirt and scraggly goatee to his infatuation with Radiohead.
The enduring beauty of Clueless, though, is in the way that Heckerling makes the movie of its time, yet set in its own unique space. The fashion and slang are both a mix of contemporary references and Heckerling-isms, and the film never undersells the fantasy appeal of hanging with pretty young plutocrats, with their touch-screen computers and sporty roadsters. It helps too that Clueless’ bright and likable cast—which includes Donald Faison, Breckin Meyer, Jeremy Sisto, and Brittany Murphy—is led by Silverstone, who’s so cheery that she can make her characters’ frank pronouncements about drugs and sex sound sensible, not hypocritical. Silverstone is the perfect vessel for Heckerling’s voice, giving a sweet spin to her suggestion that girls show a little cleavage because “this reminds guys of being naked, and then they think of sex.” Clueless is full of those kinds of lines, so funny in their guilelessness that the characters could be clubbing baby seals while they deliver them and they’d still be delightful.
Key features: A carryover of the 2005 DVD featurettes, including visits with the cast 10 years later, and extensive interviews with Heckerling and her key collaborators.