Clueless Reimagines Jane Austen’s Emma as Only Amy Heckerling Could

The Fast Times at Ridgemont High director recognized her beloved Valley girl in the timeless pages of Emma


Page to Screen is a recurring column in which Editorial Director Matt Melis explores how either a classic or contemporary work of literature made the sometimes triumphant, often disastrous leap from prose to film. This time, he hits the mall to celebrate 25 years of the ’90s classic Clueless.

Page to ScreenAmy Heckerling’s own mouth may very well have cost her an Oscar nomination. In interviews promoting Clueless — an inspired, but risky passion project that was far from a guarantee at the box office (that is, until audiences started seeing it and became absolutely smitten) — the filmmaker mentioned that she had based elements of her story on Jane Austen’s classic novel Emma. That admission caused the Academy to contradict the 48th Writers Guild of America Awards, which treated the work as an Original Screenplay, and lump in Heckerling’s witty, infinitely quotable Beverly Hills rom-com with other Oscar candidates for the Best Adapted Screenplay nominations. That year happened to also include another Austen adaptation, Emma Thompson’s brilliant, traditional take on Sense and Sensibility. Suffice it to say (and studio politics aside), Heckerling’s Cher Horowitz had a better chance of passing her driver’s test than Clueless had of besting one of the finest modern tellings of Austen on screen. Thompson’s adaptation, of course, went on to win the Oscar while Heckerling’s script spent the night at home like Cher waiting for Christian to ring her monolithic black phone.

A quarter century later, both films endure as beloved modern classics, but it’s still fun to consider what could have (or maybe should have) been come awards season.

“It is an original screenplay, if you consider West Side Story an original screenplay,” Heckerling explained of her script years later. “If you’re going to say there was Romeo and Juliet — well, [West Side Story] was a whole other world.” Indeed, Heckerling deserves major snaps for finding a modern parallel to the social stratum of Georgian-Regency England in the cliques and social circles of a wealthy high school in mid-’90s Los Angeles. Actor-writer Wallace Shawn (the film’s grumpy debate teacher turned Romeo, Mr. Hall) agrees with Heckerling. “Everything we write is inspired by great works of the past,” he asserts. “Her script was inspired by Jane Austen’s book, but it wasn’t what people ordinarily mean by ‘adapted from another medium.'” Thompson’s adaptation, of course, is what Shawn means by “ordinarily.” She beautifully captured all the romance, humor, and social critique of Sense and Sensibility while staying in period and largely drawing from Austen’s original language.

Both Heckerling and Shawn make convincing arguments for Clueless being an original, if not entirely original. Certainly, Heckerling’s totally dope update seemed out of place alongside Ang Lee’s touching take on the dating dilemmas of Austen’s Dashwood sisters. But did she get cheated out of an Oscar nomination (or even a win) by being mislabeled? While we can all agree that Heckerling’s Beverly Hills and Cher are as much hers in language, humor, and insight as Highbury and Emma belonged to Austen, the answer might come down to just how much of Emma seeped into Clueless. We might even imagine ourselves back in Mr. Hall’s debate classroom and ask ourselves if Cher, who usually relies on her powers of persuasion (including twirling her gum) over preparation, could pass an oral exam on Emma by watching Clueless.

Similarities in leading ladies immediately emerge in revisiting Emma. Austen introduces Emma Woodhouse (Cher’s classic counterpart) as young, rich, bored, and though meaning well, prone to meddle, especially in matchmaking. This repeatedly backfires and leaves her, in Cher’s parlance, totally buggin’. Austen goes on to describe her Emma as flawed from her “power of having rather too much her own way, and a disposition to think a little too well of herself.” Clearly, we see strong echoes of Emma in Cher’s flattering self-opinion, habit of overestimating her own qualifications (as a driver, a debater, or an amateur love connection), and, most importantly, knack for being completely oblivious, yet coming through mostly unscathed, every purple-clogged step of the way.

One manner in which Austen’s celebrated novel might be considered a failure is that she initially set out to make the meddlesome Emma disagreeable. And yet, at least the modern reader likely won’t be terribly put off by Emma’s machinations and misreadings. Like Cher to follow, she’s a doting daughter and ultimately does try to do well by the friends she helps, even if, as some point out, she’s serving her own interests at times, and we do see her attempt to correct her mistakes in both judgment and manners. Emma, unlike, say, the Dashwood sisters before her, is the rare Austen heroine who largely forgoes romance herself — mostly because her financial survival doesn’t depend on marrying well. In that way, she can be viewed through a feminist lens as someone operating outside the norms of her society. We see all these same qualities in Cher, and while we can definitely find humor and hubris in her Valley-girl bumbling, we’re also drawn to her pluckiness and desire to improve in addition to her ability to accessorize. Like Emma before her, there’s more of miscalculation than wrongdoing in Cher’s negotiating the social mores of her world. Both characters are incredibly likable, but, as Heckerling brilliantly coined, utterly clueless.

Clueless fans will no doubt find several other favorite characters early in the pages of Emma. Miss Harriet Smith, like Tai Frasier, possesses a “sweet, docile, grateful disposition … only desiring to be guided by any one she looked up to.” She, of course, becomes Emma’s main matchmaking project. Additionally, Mr. Elton, whose surname Heckerling keeps in her script, becomes the primary target Emma aims at when trying to match Harriet. Naturally, she misreads the object of his affections. Mr. Knightley, the brother of Emma’s brother-in-law, serves as the inspiration for Josh. Not only are the verbal volleys between Emma and Knightley among Austen’s sharpest dialogue, but he’s also the character that, even if through reprobation, causes Emma to reflect on her behavior and strive to improve. In a secondary role, the concerned Mr. Woodhouse, Emma’s father, among other things, suffers from stomach issues, and we might think of Cher chasing “Daddy” around with a glass of orange juice or wrestling a roast beef sandwich away from him during a grueling all-nighter of legal paperwork. The poor farmer Mr. Martin picks up a skateboard as slacker Travis in Heckerling’s reimagining, the secretive Frank Churchill interestingly becomes top shopping partner Christian, and it’s difficult to believe that the odious Mrs. Elton, quick to get under Emma’s skin, isn’t the spiritual sister to the “ensembly challenged” Amber.

Critics of Austen note that Emma has even less story than usual for the author. Likewise, Clueless, for all its dazzling energy, really boils down to a series of parties, hangouts, and calorie fests. Suffice it to say, what makes both the former pop off the page and the latter sparkle on the screen is how richly aware Austen and Heckerling are of their respective characters and the worlds they inhabit. But, for our sake, yes, each is the story of an oblivious, young woman who, after a satin-shoe toe-dip into matchmaking, takes on a more daunting challenge, misreads several situations, and somehow, despite everything we know about karma, comes out wearing Fred Segal on the other side. Additionally, Harriet, like Tai, gets over Mr. Elton and Mr. Knightley and falls back into the arms of her initial interest, Mr. Martin (adding allusion to Amber’s put-down of “She could be a farmer in those clothes”). And Emma, like Cher, ends up with the fella who antagonizes her most throughout the story.

While both Emma and Clueless are long on satire and style and short on plot, it’s definitely noteworthy that Heckerling updates several scenes directly from Austen’s novel. Cher’s memorable photo shoot with Supergrass’ “Alright” playfully soundtracking the posing is the modern equivalent of Harriet sitting for a portrait by Emma as Mr. Elton looks on enthusiastically. We also see Elton’s advances rebuffed in a convertible rather than a carriage (in both cases, our protagonist oblivious and the aggressor feeling the proposed match socially beneath him), and Tai, like Harriet before her, moves on from Elton by burning her collection of keepsakes. Cher’s attitude towards high school boys stems directly from Emma’s unorthodox outlook on marriage; Josh, like Knightley before him, does Tai a solid by dancing with her at a party, which leads to additional complications; and Cher’s epiphany about Josh comes straight from the pages of Emma, granted with a few more shopping bags.

And yet, something feels lacking in calling Clueless an adaptation, like there needs to be a new category created for it.

“I wasn’t trying to say, ‘Here’s Emma,'” Heckerling explains of her intentions. “I was trying to say that Emma makes perfect sense right now. There’s so much that hasn’t changed.” In reading more about the creative process the director undertook, it seems less that Heckerling merely tried to modernize or transport Emma and more that she came to realize that the type of character she wanted to build a world and story around — a young, headstrong girl who fails to see the obvious — already existed in the pages of Austen. That speaks to both the genius of Austen and the ingenuity of Heckerling to recognize the ongoing relevance of the Emma type in a very different time and place. In that sense, it’s not so much that Cher couldn’t exist without Emma, even if her youthful mishaps owe Austen’s novel a sizable debt. It’s more that we believe if Emma Woodhouse were to walk a mile in Cher’s pumps and have a grungy, greasy high school guy with baggy pants and a backwards cap throw his arm around her, we wouldn’t be entirely shocked to hear an emphatic “As if!”

Editor’s Note: All merch on the Consequence of Sound store, including our Beverly Hills Plaid face mask, is BOGO 50% off through July 31st. Proceeds benefit our independent publication, as well as MusiCares’ COVID-19 relief fund.

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