Clueless: Remembering and Reimagining a Classic

I recently saw Alicia Silverstone in a Rakuten commercial and was all at once stricken with wistfulness. She was reprising her role in Clueless, the classic filmic send-up of 90s high-school life, and she had a familiar, jaunty tune undergirding her consumerist hijinks. In that 1995 film, Silverstone plays 15-year-old Cher Horowitz, a high school sophomore. In the 2023 commercial, Silverstone could have passed for Horowitz as a senior, as she’s aged imperceptibly in the 28 years since the film’s release. When an extra playing a classmate asks “aren’t you a little old for high school?”, Silverstone responds with a knowing wink. That extra looks more out of place playing a high-schooler than Silverstone does.

Clueless was and still is the 1990s. The film’s dialogue captured the artful vapidity of the era’s argot, as well as the insouciance of its delivery. The cast embodied 90s gloss, and not just in their costuming. Vacuous or not, the film’s Valley Girl characters expertly navigated the dark corners of human experience. They were materially replete and sexually discerning. Their intuition for human relationships far surpassed the experience of their teachers and parents. The principal characters may have sounded like airheads, but they no doubt had blisteringly high IQs. They were adept. They epitomized distinctively feminine action in an epoch of passivity (a torpor that was most often gendered male). The film and its characters contemplated the existential toll of living in a decade that was relatively comfortable compared to its predecessors (and certainly compared to those that followed). Moreover, Clueless retold Jane Austen’s Emma, touching on comparable themes of gendered space and the hazards of matchmaking.

But apart from all that, at twelve years old, I had a crush on Alicia Silverstone. I’m not afraid to admit this, as I cannot think of a more wholesome celebrity crush for a boy on the cusp of pubescence. This was not the celebrity crush of a teenage boy that quickly turns Onanistic. Rather, this was a chaste infatuation. I didn’t really understand anything of what women were beyond what I perceived to be an enigmatic alterity, and Silverstone ably embodied that mystery. And yet, paradoxically, Silverstone possessed an obvious and un-intimidating prettiness. Her distressed expression on the Clueless movie poster dizzied me. Her name itself held sinuous allure, what with all its sibilants and syllables, in addition to its internal alliteration. The act of speaking her name took one’s tongue on a tortuous trip. There was a distinct gravitas in the name’s sheer length along with the craggy, shimmery imagery of the surname. (“Alicia Silverstone’’ was all the more beguiling before I came to realize I’d been mispronouncing the “c” as a dental sibilant — uh-lee-see-ah — rather than the correct palatal.) In seventh grade, Alicia Silverstone acquired a timelessness for me. I assumed that she was and always would be a Hollywood leading lady, and a perennial sex symbol. I looked forward, I think, to growing up with her. My twelve-year-old imagination couldn’t fathom anything but that.

Never mind the fact that I hadn’t seen Clueless. I didn’t need a screening to build an apocryphal story-scape for the film. I was an interior child, and so I could bore imaginally into that poster and invent everything that took place in Clueless’s version of Beverly Hills. Indeed, I imagined Clueless as I imagined California. I saw a world of short skirts and high socks and platform heels. I saw perceived slights and PG-13 intrigue. I saw disenchanted sexuality, where Judeo-Christian moral hang-ups had become irrelevant. All this came swaddled in plaid. And while the movie poster may have led me to a somewhat bastardized understanding of the film itself, I still had the soundtrack cassette.

The Clueless soundtrack was the backing track to the second half of seventh grade for me. If you wanted to digest the 90s in sound, the Clueless soundtrack would make for an apt sonic abstract. It begins with a banger, namely the Muffs covering “Kids in America” and adding some much-appreciated 90s zest to that 80s British synth-pop. Of course, at age twelve, I hadn’t heard of Kim Wilde, so this became the definitive version of the song for me. Then comes Luscious Jackson’s moany, uncompromisingly sexual “Here”, or, as I knew it, “Get on the Floor, Let’s Dance Some More.” Then there are offerings from Radiohead and Counting Crows — a more 90s combo I cannot conceive. The Beastie Boys’ were my favorite band as a pre-teen, and I bought the tape for their contribution, “Mullet Head.” This low-fi faux hardcore punk track isn’t the Beasties’ best cut by any means, but it’s not without cultural impact. Arguably, the title was the first attestation of the term “mullet” with reference to the notorious rat-tailed haircut that persisted through the 80s and 90s. In this sense, the song has an auspicious place in history. And then there’s the self-indulgent “Super Model,” which I probably enjoyed too much for a heteronormative boy (standards of heteronormativity and gender sensibilities having been more neurotically guarded in that era, especially in my prairie home). With all that being said, it sounds as if the putative enduring cut is Supergrass’s “Alright,” the jaunty, upbeat, Britboy pop that serves as the backing track to Rakuten’s recent Clueless reprisal. All told, Clueless delivers one of the finest motion picture soundtracks ever arranged, the inclusion of The Mighty Mighty Bosstones notwithstanding.

From this collection of songs alone, as well as the pictures in the liner notes, I was able to conjure up a soundscape in my mind that contained all of what Clueless was and could be. It was a surreal world of adult teenagers and uncanny grownups entangled in romance and wealth and excess, all of it hyperbolic and sleek. But the adults were almost wholly peripheral. The “Kids in America” were the ones who were really doing the living. They were the stars. In the center of it all was Alicia Silverstone, this angel-faced sylph who wore a slinky red dress and a perpetual look of exaggerated umbrage. This, to me, was the Clueless experience. Surely, this was the teenage I would grow into.

I believe I may have seen parts of Clueless when I was in college, stumbling upon it as I channel-surfed after a long Saturday night of schoolwork. By then, 9/11 had happened, society had hardened, and, despite ideological commitments to the contrary, I had personally done little to spurn Judeo-Christian moral hang-ups. If anything, my life had become monastic . . . save for the Onanism. The interior child had grown into an introverted man. As such, Clueless doubtlessly struck me as childhood fluff, and I likely flipped back and forth between channels, keeping the sound low. On a subconscious level, perhaps I was ashamed of my childhood crush on Silverstone, which bespoke some earlier, underdeveloped stage of my psychosexuality. Whatever it was, the teenage I’d expected based on my imagining of Clueless was far from the one I got. I remember nothing of the plot.

For years, I don’t recall thinking of Clueless at all, not even in passing, not even when I screened Heathers and Mean Girls. The soundtrack got buried in a box with the rest of my cassette tapes. I can’t recall watching a single movie with Alicia Silverstone in it, and hers was not a name seen or heard in the headlines and celebrity gossip. Alicia Silverstone did not become a timeless sex symbol, but rather someone remembered mostly for one movie tied to one particular time period. Maybe, in the most abyssal depths of my psyche, I was disappointed at this development (or lack thereof). I’d almost forgotten her name entirely.

But then I saw that Rakuten commercial, with Alicia Silverstone capering through the campus and classrooms of Beverly Hills High, and I was shuttled back to the reveries of my pre-teens. I was dizzied all over again, not so much by Silverstone’s beauty (enduring though it has proven to be), but by the rediscovery of the vast imaginal space into which I had spent so much of thirteenth year escaping. It was as if now, on the precipice of 40, I’d finally been admitted into Beverly Hills High. Suddenly, that surreal world, with all its lustrous romance and wealth and excess, was available anew, and I was experiencing all its facets in the span of that TV spot. All the potentialities I’d conjured for that movie I’d never seen swirled up again within me, drenched in adolescent hope and an innocent, proto-sexual vision of romance. All the world-building I’d done in lieu of actually seeing Clueless came back to the fore, and all the songs from the soundtrack played in my head at the same time. . . “We are young, we run green” and “Everybody live for the music-go-round . . . .” I found my heart beating faster in anticipation of the future, something which hasn’t happened for me very much since the 2010s, and probably not much for anyone since the 2020s began.

When I saw that commercial, it time-warped me back to a better time. Of course, almost everyone thinks the decade in which the bulk of their late childhood and adolescence took place was the best one, but with the 90s, this sentiment cannot be simply written off as chronocentric bias. In the 90s, things were easier. You could be a slacker, and that was enough to build an identity on. It was pre-9/11, after which patriotism and a hawkish attitude toward international conflict became du rigueur if you lived in non-coastal America. The 1990s were pre-Trump and pre-post-Truth, and there were still basic facts that people of opposing political stripes could agree upon. The 1990s were pre-pandemic and post-AIDs, and it still felt like America could handle any given crisis it faced. Nuclear conflict was an increasingly distant memory, and a Russian invasion of Ukraine would have seemed farfetched. In the 1990s, most could never have pictured a bunch of angry Americans storming the Capitol to overturn the results of an election . . . and certainly not for the purpose of keeping an insolvent huckster like Donald Trump in power.

We were naïve if we believed things wouldn’t change, but things were stable enough throughout the 90s that it seemed possible they might just stay that way forever. Perhaps America as a society began to coast. Nonetheless, I think the 90s was a time when a healthy percentage of people had hope for the future. This was true at least for me, given the pivotal time of my life I was in, right on the cusp of pubescence. I assumed at that point that life would just rollick right along like in that song “Alright”; indeed, everything would be “Alright.” It appears as if I may have been projecting a child’s naivete on the world, the same way I had projected it onto an Alicia Silverstone movie I’d never seen.

Regardless, that Rakuten commercial walloped me with a nostalgia that was almost painful, and I’m likely not the only viewer who felt the same way. Cher Horowitz’s dedication to shopping makes her a perfect spokes-character for a website that pays you to shop, but the commercial can be so much more than that. Based on the emotions spawned by this 30-second commercial, I’m led to believe that the 97-minute movie upon which it is based can only foster and expand these feelings of nostalgia and wistfulness. Clueless, then, could be the perfect escapist film for the 2020s. It offers a digestible slice of a better time, and this is a dish well-deserved on account of the fact we’ve had to stomach several consecutive unsavory decades (with a promise of many more distasteful years to come).

And while Alicia Silverstone didn’t become the it-girl of Hollywood, she may have attained to something more profound. Through a single iconic role, not to mention some extremely gentle aging, she’s been able to enkindle some nostalgia in Rakuten customers and inject some hope into some of us who haven’t aged so gently. On the strength of Cher Horowitz alone, Alicia Silverstone has prevailed. Evidently, she has endured for me, and I can’t be the only one. Her unassuming smile awakened something in me that has long since shed its pubescent and sexual valences . . . quite simply, she reminded me that there were and are better times. There could be better times again. Through Clueless, we can live some fragment of a future we promised ourselves in which the 90s echoed on; we can relive a time when we were, well, clueless, as to where American consumerism could take us. Maybe this is as good a time as we can have at present.

Or maybe the content of the commercial is enough: perhaps we should just give up on existential rumination and give ourselves to a website that pays us a pittance for shopping.

I’m not going to start shopping on Rakuten anytime soon, but I am going to buy a copy of Clueless on Blu-Ray. Even though I haven’t properly seen the film, I have more than just a clue that I’m going to love it. Of course, the film comes highly touted, and if it captures even a little bit of Emma, then it’s going to be fantastic. Even seeing the late Brittany Murphy again will no doubt bring on a bittersweet frisson. But whether I enjoy Clueless’s contents or not, I know it will transport me to a landscape and a soundscape from a time that was, in my life and in the world, objectively better. As such, there are better times around the corner for yours truly when he screens Clueless for the first time.

You’re never too old to keep hope alive. Thank you for reminding me of that, Alicia Silverstone.