'Clueless' Is Amy Heckerling's Pop Culture Masterpiece

To me, Amy Heckerling is the real reason Clueless remains a piece of pop culture iconography. That might not be too terribly original, especially when said decades later. Since Clueless' release on July 19, 1995, the movie has maintained a top spot in the zeitgeist, a consistent and reliable wellspring for quotes, music, fashion, and discussion. Alicia Silverstone has even reprised her role as Cher in an iconic Superbowl ad. It is hard to imagine what Clueless would be today if it had been written or directed by anyone other than Heckerling. I'm not sure if I want to even imagine what that alternate timeline would look like. Instead, I'd rather take you on a journey highlighting all of the ways in which Heckerling's vision of a '90s teen molded in the fashion of Jane Austen's Emma is, to this day, basically a masterpiece.

What Is 'Clueless' About?

A quick FYI: Clueless follows Beverly Hills teen Cher (Alicia Silverstone), daughter of a prominent lawyer (Dan Hedaya), who moves through the world with the confidence of a young woman upon whom the sun constantly shines. With the arrival of new girl Tai (Brittany Murphy), Cher and BFF Dion (Stacey Dash) take it upon themselves to give their friend a makeover and help steer her toward true love with one of the many eligible high school boys at their school. Cher is very much like her Austen counterpart, happy to pair up the entire world without actually understanding the true complexities of love. Luckily, former step-brother Josh (Paul Rudd) is always around to give her a much-needed reality check as she tries (to varying degrees of success) to bring happiness into the lives of everyone around her.

Up until Clueless' release, Heckerling had dealt primarily in comedies with either male protagonists, male-dominated comedic sensibilities, or something more directly speaking to male anxieties both at home and socially. Fast Times at Ridgemont High, Johnny Dangerously, National Lampoon's European Vacation, and the first two installments of the Look Who's Talking franchise making up the first chapter of Heckerling's directing career, which spans more than four decades. As a feature-length screenwriter, Heckerling had both Look Who's Talking and the sequel, Look Who's Talking Too, under her belt. Across the board, the movies Heckerling wrote and directed before Clueless were major successes, with those successes involving some combination of utilizing the star power of a respective movie's leading cast, seeing the benefits of the movie developing a cult following, and some of those movies enjoying the fruits of box office success.

'Clueless' Marks a Shift in Amy Heckerling's Career

Clueless marks a noticeable shift in Heckerling's career — and it's an interesting shift to boot. Rather than working to stake out property in the crowded territory of male-focused comedies directed by men (although her efforts are damn good), Heckerling turned her attention to the world of Southern California teens and, specifically, female stories. It's a shift in creative focus which would come to define Heckerling's work as a director from there on out, with Clueless arguably serving as the strongest example of Heckerling's ability to blend her comedic voice with the ways in which women's lives are depiected onscreen, in all their multi-faceted glory.

The Clueless script was born out of failed attempts to capitalize on the success of Look Who's Talking Too, including a script rejected by Disney for being "too smart," leading Heckerling to mimic her reaction — "And so I said, 'All right, you want dumb? I’ll show you dumb...'" — in a 2017 profile at The Ringer. Heckerling also shed light on the inspiration for the story while telling Interview in 2018 the history behind the deliciously savage "You're a virgin who can't drive" insult uttered by Tai late in the film's second act.

"I was writing a character that I thought was the very opposite of myself, a character that was really happy and if there was any negative criticism, she just didn’t take it seriously because she had confidence, and if her father was angry she thought he was just being cute. So I ran with that and just looked for sources of happy characters to get inspiration from. The two big things, of course, were Gentlemen Prefer Blondes [1953] and Emma [1996]. My daughter just picked up Gentlemen Prefer Blondes , the book, and was amazed at how wonderful it is."

Heckerling's script, rooted in these two books and later enhanced by a variety of on-set tweaks by cast and crew members, is one part of why Clueless is still so beloved to this day. Heckerling has not only masterfully laid Austen's Emma narrative onto the world and lives of privileged Southern California teens in the mid-90s, but has managed to fine tune the twists and turns of that much older story so that nothing feels forced or clunky. Even when Heckerling's writing veers away from maintaining its Emma parallels, it's clear she has spent time studying and working to understand the slang and cadence of language utilized by the people inhabiting that very specific time and place. Take the scene where Cher is debating the "ensemble-y challenged" Amber (Elisa Donovan). There is such an attention to detail in the structure of Cher's language that it tells you everything you need to know about our protagonist, including her unique outlook on life which will eventually guide every decision she makes for the rest of the movie.

It only gets better when Heckerling is in director mode. Heckerling's script understands it's important to never make Cher or her friends the butt of the joke, even if they're constantly being #ExtremelyTeenage in how they move about the world in their singular point-of-views achieved by their privilege and popularity. While in director mode, Heckerling consistently hammers this point home, showcasing jokes both visual and from the page which highlight the absurdities of Cher's life and her daily dramas: The computer which helps her put together an outfit, preparing for her date with Christian by creating a lighting scheme, flipping out about a potentially ruined pair of designer heels while attending a party in the Valley, realizing she loves Josh as a giant fountain comes to life, and so forth. without taking the stance that Cher, her friends, or her life is absurd. Heckerling's direction of the Clueless cast helps drive this home, too, with everyone putting in sincere, nuanced work which helps make the weirder, sharper, and darker comedy of Heckerling's script just as light and enjoyable.

Look, there's not too much in the way of revelatory statements I can say about Clueless which haven't already been said in the over two decades since its release. But, in thinking about this movie and what really stands out to me after all these years, I keep circling back to Heckerling's contributions to this movie. Hell, this is Heckerling's movie, through and through. It's the result of great timing, a distinct voice, a collection of generation-defining actors, music cues so perfect it hurts, and outfits so good it hurts even more — all of it was possible because it began with Heckerling and an idea based on Emma and Gentlemen Prefer Blondes.

To this day, Clueless is a movie we acknowledge as reclaiming the "ditzy" narrative applied to women for decades; it's a ground-shaking entry into the comedy genre; it preserves the memory of a bygone era while keeping it thoroughly accessible to newcomers; it's a '90s teen comedy continually referenced, sourced, parodied, and paid homage to elsewhere in pop culture. The legacy of Clueless is cemented. Heckerling deserves recognition for her work on Clueless, to this day and all these years later. So give it to her.

Clueless is currently streaming on Paramount+ or Amazon Prime Video.

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