A Fully Grown Man Watches ‘Clueless’ for the First Time

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Clueless turns 20 on July 19, and Flavorwire is celebrating all week with a series of tributes to Amy Heckerling’s era-defining teen film. Click here to follow our coverage.

I’ve been lucky. I’ve never been blackmailed by someone who figured out my darkest secret — not even after I asked if “share Horowitz” was some sort of slang for “pass the lox,” or after I asked whether Sartre had guest starred on the “way existential” Ren and Stimpy. But as anxiety mounted that that day would at some point come, I realized it was time to come out with my dirty little secret — that I was clueless about Clueless — and instead of burying my shame, try to amend it with a viewing of this allegedly critical apotheosis of ’90s high-school glorifying nostalgia. What better time than on Clueless’ 20th anniversary?

In watching the film for the first time in the nonjudgmental vacuum of my apartment, I was able to question the source of its canonical nostalgia — more so than if I’d felt obligated to simply laugh along with my friends to “classic moments.” What’s most striking about watching Clueless for the first time in 2015 is its delightful pairing of (vague) social satire with optimism, and its total tenderness. It’s hard now, however, not to hear the Cali-inflected speech through the filter of Ryan Trecartin, Liam Kyle Sullivan AKA Kelly’s “Shoes” (which, arbitrarily, would likely not get its own show at PS1) and equally — if accidentally — sinister acts like Iggy Azalea and the #Rich Kids of Beverly Hills. All these things evolved from movies like Clueless, but distorted the aesthetic through the growingly pessimistic cultural times.

Clueless, on the flip side, initially presents cartoonish characters, but most of them reveal themselves to be surprisingly complex, bestowed with fullness by writer/director Amy Heckerling’s seemingly adamant humanism. As Sarah Seltzer said in her recent piece about Clueless as an Emma adaptation, “Cher Horowitz illuminates Emma Woodhouse because they both exist in that precarious realm where lovable threatens to tip over into loathsome, but doesn’t” — the operative word being the last.

Generally, back in Clueless times, the pop mainstream was similarly concerned with making the wealthy/celebrities look friendly and relatable (compare Britney’s 1998 “Hit Me Baby” video to 2013’s “Work Bitch”). Today, the pop video zeitgeist — banking on aesthetically critiquing “the machine” while perpetuating it — largely will, thanks to the marks made by early Gaga, present our wealthy icons as alien, caught in an extravagantly hollow world of material goods (note, again, how Clueless was revamped through the trademark artifice of Azalea) that’s meant to tread a coercive line between horror and seduction.

The trend nowadays seems to be the incessant amplification of vacuity, an empty coupling of capitalist repugnance and capitalist allure. Even when they’re trying to woo, these depictions do so through horrific excess —and it’s now pretty expected for wealth to be portrayed as such. Thus, especially insomuch as satirizing wealth goes, I wonder if it’s possible to do it in such a warmhearted, positive way as Clueless without feeling completely out of touch.

The climate today is as different economically it is culturally: in 2006, an article in The Economist detailed how in the first five years of the new millennium, wages for the average worker had only risen by 5%, while in the five previous years, they’d risen by 6%. In 1993, stats show that between 12 and 13% of America’s wealth was owned by 1%-er families, while in 2013 it was above 20%. And, there’s the fact that despite corporate profits having doubled in the last 25 years, the overall median income in most counties has decreased in the last 15. It’s hard to feel all bubbly inside about any of that, even if those stats would at least help a now-30-something Cher Horowitz curate a killer designer-only ensemble and ultimately fall in love with Paul Rudd.

That’s to say, with the rising Occupy-era wealth gap extremes have come rising bitterness and disillusionment, especially from many of the liberal, starry-eyed nostalgia-monger writers (like myself). Watching and writing about Clueless thus becomes an impeccable measure of the way increased wealth stratification has affected one’s cultural palette: the movie is undeniably superb — especially as an undyingly funny relic — but if it came out now, updated but with a similar tone, what would critics think?

The singularly and wonderfully ’90s-optimistic feeling of Clueless vs. the current state of the zeitgeist is even notable is the use of uptalk in the film, as opposed to the vocal fry of the present day — the former denoting curiosity and even enthusiasm, the latter denoting a culture of disenchantment. In watching Clueless, for me, it seemed that the joyous feeling it provides is quite particular to the era; one of the reasons it’s still so beloved is because if it were made now, it’d seem far too friendly a portrait of wealthy ignorance.

Rather, we can look back on it and recall a time when we could afford a little more satirical kindness. Nineties nostalgia doesn’t so much come from the desire to go back to a socially less aware — and to some extent, less advanced — time, but rather, on occasion, to be clueless about the very understandable trends of contemporary cultural pessimism. Strange that I hadn’t, after all this time, seen the film that’s become — by name and by nature — the beacon of that escapist notion. But at least no one can blackmail me for it now. Not that they’d get much out of me, anyway — #wealthgap.