After 25 years, Clueless is still our cleverest Jane Austen adaptation

It took Amy Heckerling a while to realize she’d written an Emma homage. Her TV pilot script centered on a rich, sunny young woman who approached the world with a can-do attitude—a savvy dumb blonde in the vein of Marilyn Monroe in Gentlemen Prefer Blondes. When Heckerling’s agent suggested the project might work better as a feature, she sought narrative inspiration in one of her favorite Jane Austen novels from college. Only then did she realize that her meddling but well-meaning 16-year-old Beverly Hills princess protagonist was really just a riff on “handsome, clever, and rich” Emma Woodhouse, an heiress who “had lived nearly twenty-one years in the world with very little to distress or vex her.” Thanks to an 1815 novel, an iconic 1990s teen movie got its structure.

Clueless, which turns 25 this week, is actually a remarkably faithful Austen adaptation. Not in setting, of course; Austen’s characters were far from computerized closets and “loqued out” Jeep Wranglers. But in terms of tone, character, and even detailed plot points, writer-director Heckerling translates Austen’s prose for a modern audience with remarkable fidelity. What she understands—and what too many casual consumers of Austen’s work miss—is that in addition to her romantic aims, the author wrote hilarious satires of the moneyed world of England’s landed gentry. Clueless transports that satirical eye to Beverly Hills, with a glossy opening montage in which Cher Horowitz (Alicia Silverstone) earnestly explains, “So okay, you’re probably thinking, ‘Is this, like a Noxzema commercial, or what?’ But seriously, I actually have a way normal life for a teenage girl!”

Heckerling lets the cheeky social satire take center stage without the historical trappings that can prove alienating for some modern audiences. So while Emma would get period adaptations in a 1996 Gwyneth Paltrow film, a 1996 Kate Beckinsale TV movie, a 2009 Romola Garai miniseries, and this year’s charming Autumn de Wilde adaptation starring Anya Taylor-Joy, none have as perfectly captured Austen’s dry comedic voice as Clueless. In fact, Clueless is an ideal primer for those looking to understand Austen’s signature blend of romance, comedy, and social commentary. So it’s only appropriate that it hit theaters a few months before Andrew Davies’ Pride And Prejudice miniseries and Ang Lee’s Sense And Sensibility officially kicked off the Austen mania of the ’90s.

Of course, you don’t need to know anything about Emma to appreciate Clueless as a comedic masterpiece in its own right. It became a sleeper hit and a cultural phenomenon in 1995—the rare film that connects with both audiences and critics and then goes on to be embraced by every subsequent generation that comes across it. Clueless singlehandedly revived the teen movie at a time when that genre seemed all but dead thanks to the glut of sex comedies and John Hughes high school romances that had filled the previous decade.

Though Heckerling had kicked off that trend in the first place with her debut feature, 1982’s Fast Times At Ridgemont High, by the mid ’90s she couldn’t find a studio interested in a teen comedy with multiple female leads. Never mind that Heckerling had a proven track record with big hit comedies like National Lampoon’s European Vacation and the nearly $300-million grosser Look Who’s Talking. It took producer Scott Rudin to rescue Clueless from endless turnaround and give it a home at Paramount Pictures.

As Clueless evolved the teen rom-com into its ’90s form, Heckerling took one unexpected point of inspiration from the previous decade. “The most successful character in anything I’d ever done was Jeff Spicoli in Fast Times,” Heckerling told Entertainment Weekly in 2012. “People think that’s because he was stoned and a surfer. But that’s not it. It’s because he’s positive. So I thought, ‘I’m going to write a character who’s positive and happy.’ And that was Cher.”

Though Austen once joked that Emma was “a heroine whom no one but myself will much like,” the key to the novel’s success is the affection Austen clearly feels for her serenely self-delusional protagonist. And that’s exactly how Heckerling feels about Cher, the queen bee of Bronson Alcott High School who wields her powers (mostly) for good. She looks after her father’s health. She fully intends to break for animals. And she views makeovers as the ultimate act of charity. Like Emma, Cher wants to help people. And like Emma, she lacks the humility to keep her worst meddling impulses in check. “The real evils, indeed, of Emma’s situation,” Austen wrote, “were the power of having rather too much her own way, and a disposition to think a little too well of herself.”

Clueless subs in teen cliques for class distinctions and high school ragers for balls, but it otherwise keeps most of Emma’s plot intact. Cher adopts a charity case in the form of a lower-status woman (Brittany Murphy’s brassy transfer student Tai), steers her away from a guy who’s clearly perfect for her (Breckin Meyer’s sweet stoner Travis), and ultimately comes to realize that she’s actually the one who’s totally clueless about matters of the heart, especially her own. Much as Emma discovers “with the speed of an arrow” that she’s in love with her haughty neighbor Mr. Knightley, a glowing fountain punctuates Cher’s own revelation that she’s “majorly, totally, butt-crazy in love” with Josh (Paul Rudd), her pretentious one-time stepbrother.

To her credit, Heckerling goes all-in on the inherent weirdness of the Emma/Knightley pairing—something other adaptations often try to smooth over. In the book, Knightley is not only Emma’s brother-in-law, he’s also 16 years older than her and has served as a sort of paternal figure since she was born. While Clueless shrinks the age gap, it keeps the vaguely incestuous setup by having Josh and Cher be even more closely entwined in pseudo-siblinghood. It’s a testament to Silverstone and especially Rudd that they’re able to sell the romance despite the strangeness of the setup.

For her teen cast, Heckerling wanted actors with both a worldly maturity and a childlike innocence. She hired 17-year-old Silverstone (then best known for starring in Aerosmith music videos) after a single lunch meeting because she was charmed by the way the young actress kept leaning down to her straw instead of bringing the drink up to her mouth. Though the hippieish Silverstone originally struggled to connect to a character she found materialistic and annoying, Heckerling could see there was an innate Cher-ness to her. Silverstone’s real-life mispronunciation of the word “Haitians” (and Heckerling’s savvy instinct not to correct her) led to one of the film’s signature comedic moments as Cher demonstrates both her empathy and her privilege while arguing a pro-refugee stance in debate class.

While Clueless adds some archetypes from the teen movie handbook, like Cher’s loyal bestie Dionne (Stacey Dash), frenemy Amber (Elisa Donovan), and Dionne’s puppyish boyfriend Murray (Donald Faison), characters like Jeremy Sisto’s entitled Elton come straight from Emma. (There he’s Mr. Elton, a social climbing vicar.) Elsewhere, Heckerling seamlessly subs in a photo shoot for a painted portrait and some mall hooligans for a gypsy attack. The burden of attending an event thrown by social inferiors becomes Cher scoffing at an invite to a party in the Valley.

In one smart adaptation choice, Heckerling plays around with the novel’s structure a bit. Though Emma opens with its heroine having already made her first successful match, Clueless follows Cher as she conspires to pair her debate teacher Mr. Hall (Wallace Shawn) with her world history teacher Miss Geist (Twink Caplan, also an associate producer on the film), the better to get some lighter grading. Watching the rush of that first matchmaking success helps us empathize with Cher as she continues to deploy her powers of persuasion with varying degrees of selflessness. Plus it cleverly allows Clueless a traditional Austen wedding ending without sending any of its teen characters down the aisle. (“As if! I am only 16, and this is California, not Kentucky.”)

It’s a testament to Austen’s insightful story that some of it doesn’t need updating at all; sexual harassment in a car is much the same as in a carriage. The hilarious scene where Tai burns mementos from her brief crush on Elton also comes directly from the novel. As does the sweet moment where Josh saves Tai from social embarrassment by asking her to dance, the same way Knightley gallantly does with Emma’s protégé, Harriet Smith.

Heckerling’s most interesting update comes in the form of Christian (Justin Walker), the fashionable, Rat Pack-loving transfer student Cher initially tries to seduce before learning he’s gay. He’s a stand in for Frank Churchill, the dashing visitor who publicly flirts with Emma to cover up the fact that he’s secretly engaged to the lower-born Jane Fairfax. In a way, however, Christian reflects aspects of both Frank and Jane (who doesn’t get a direct counterpoint in the film). Like Frank, Christian is an object of desire for the heroine’s ultimately not-all-that-intense crush. But like Jane, there’s a sympathetic set of high stakes for why he might not immediately reveal where his heart actually lies.

Clueless’ matter-of-fact treatment of Christian and his sexuality is one of the many places Heckerling maintains the spirit of the novel but updates it for the 1990s. While Emma learns to accept some humility and stop meddling, Cher’s arc is more explicitly about becoming a better, more socially conscious person. She commits to a “makeover of the soul” and volunteers to captain her school’s Pismo Beach disaster relief effort. Even then, however, Heckerling doesn’t lose her satirical bite. The first thing Cher thinks to donate to the disaster victims are her skis.

Of course, Clueless didn’t really reflect the ’90s so much as create a funhouse-mirror version of the decade. Heckerling invented a whole new vernacular with the film’s nonstop slang—some of which she pulled from actual teens but much of which she made up herself. Meanwhile, costume designer Mona May created an unforgettably bonkers high-fashion aesthetic at a time when shapeless grunge fashion was all the rage with real-life high schoolers. As May explained in a great 2016 interview with Harper’s Bazaar, “Amy’s vision really was to make this movie a girly movie… This movie to me is really a celebration of the girl in all of us—feminine, sweet, fun, flirty, adorable.”

In many ways, the “girl power” branch of ’90s feminism shares a lot in common with the proto-feminism of Austen’s early-19th-century novels. Austen and Heckerling subversively celebrate the intelligent inner lives of young women who society might be inclined to look down upon. (Cher’s knowledge of Hamlet may come courtesy of Mel Gibson, but she knows her Polonius quotes.) Yet Emma and Clueless also tell stories of women who are happy to live within their prescribed social roles, rather than challenge the system.

Though there’s a progressive edge to the way Austen’s heroines assert their independence in their determination to marry for love, the fact that they’re rewarded with financially prudent, socially acceptable matches means Austen’s satires are ultimately loving and a little conservative, rather than caustic and rebellious. That’s very much how Heckerling approaches Clueless’ over-the-top world of teenage privilege too. Unlike the darkly satirical Heathers, there are no real villains in Clueless. Even Cher’s terrifying litigator father is a sweetheart when it comes to his beloved daughter. (Heckerling wanted to cast the role with “someone who might play a hitman in other movies,” which eventually led her to the pitch-perfect Dan Hedaya, who considers the project one of his favorite moviemaking experiences.)

Ironically, the sunniness of Clueless was literally manufactured. It rained for four weeks straight during the shoot, so cinematographer Bill Pope (a go-to collaborator for Sam Raimi and the Wachowskis) had to fake the California sunshine. It’s an apt metaphor for the loving, can-do spirit that fueled the whole film, which served as a launching point for pretty much all of its young stars. Brittany Murphy’s untimely death in 2009 has given Clueless even more poignancy now, as her effervescently guileless performance is key to so much of what makes the film work. (In a 10th-anniversary featurette, Murphy laughingly revealed that at the time she delivered Tai’s iconic insult, “You’re a virgin who can’t drive,” both of those descriptors applied to her.) As Breckin Meyer sweetly recalled during a 2012 reunion, “I didn’t have to act being in love with her. Once you met her, you couldn’t help it.”

As a touchstone for everything from Halloween costumes to Iggy Azalea videos, Clueless is at no risk of losing its exalted place in pop culture history. Yet even so, it doesn’t always get the credit it deserves for its massive influence on the next two-and-a-half decades of pop culture. You can most obviously see its impact in the subsequent wave of literary-inspired teen comedies like She’s All That, 10 Things I Hate About You, She’s The Man, and Easy A. But Clueless also helped launch a whole new subgenre of upbeat, sneakily smart “girl power” comedies like Legally Blonde, Josie And The Pussycats, Bring It On, Romy And Michele’s High School Reunion, and Mean Girls. Heckerling proved a lighthearted comedy aimed at teenage girls didn’t have to speak down to its audience. That had a ripple effect that’s still ongoing today.

Just as the romantic comedy genre would look a whole lot different without Jane Austen, movies, TV, and even fashion would look a whole lot different without Clueless. In the same way that Emma subconsciously seeped into Heckerling’s initial script, Clueless has no doubt influenced generations of filmmakers who grew up watching and rewatching it. Like so much of Austen’s work, Clueless is both deeply of its time and yet somehow entirely timeless. It’s “classic,” to quote Cher, and, most importantly, you don’t have to be a snob and a half to appreciate it.

Next time: From Austen to Shakespeare: Kenneth Branagh made The Bard a hit with 1993’s Much Ado About Nothing.