I practiced detachment. … I became a virtuoso of deceit. It wasn’t pleasure I was after, it was knowledge. … And in the end I distilled everything to one wonderfully simple principle: win or die.
—The Marquise de Merteuil, Dangerous Liaisons
I’m starting to understand the appeal of heroin, or womanizing, or whatever it is that writers do.
—Dan Humphrey, Gossip Girl
As played by Ed Westwick, Chuck Bass is a sybaritic little monster, the son of a billionaire, and arguably the most compelling character in Gossip Girl. He has the haircut and the daddy issues and entirely the mien of Joaquin Phoenix’s pissy, pouting boy-emperor Commodus in the movie Gladiator, and he has a catchphrase—“I’m Chuck Bass,” a kind of personal mantra whose intended purpose is to reassure him of his own importance, and whose actual purpose is to reassure the audience that he’s an asshole. Like the other main characters in the show, Bass is a student at an elite private high school, but behaves as if he is a forty-year-old villain from a movie about Wall Street. He drinks scotch, dresses like an even preppier Patrick Bateman, and regular one-on-one sex will not do for him if there is any possibility of sweet-talking his way into a threesome, or a foursome. There is something to be said about his being born on third and hitting it in triplicate, but I am hesitant to be the one to formulate the joke.
In the pilot episode, he also tries to rape two separate women. It seems crucial to explain this upfront, partly because Gossip Girl itself does not make much of an attempt to make sense of it in its later episodes, and partly because of all of the series’ twists and turns, it is the one that seems truest to life. Both times, it is entirely conceivable that rather than a rapist, Bass sees himself as a particularly strident seducer of women, aiming to bestow on them the invaluable gift of his sixteen-year-old sexual prowess. Both times, it is also clear to even the most casual viewer that what’s happening is assault. When you’re the son of a billionaire, I wrote inevitably in my notes, they let you do it. You can do anything. Grab ’em by the pussy. If Chuck was sixteen in 2007, when the first season of Gossip Girl is set, I calculated that by 2029, he could be president.
Created by Josh Schwartz and Stephanie Savage, who in 2007 were best known for The O.C., Gossip Girl is tonally bizarre; it is a teen romp, dazzlingly staged, whose characters are as amoral and unpleasant as fully-grown gangsters. Where The O.C. was Californian enough that the locale inspired not only the title but the theme tune, Gossip Girl was deeply New York: cocky, jaded, swift and mean, and full of kids who had grown up entirely too fast.
The showrunners of Gossip Girl have often talked about drawing their inspiration from Dangerous Liaisons, with Chuck Bass effectively functioning as a modernized Vicomte de Valmont. Certainly, the version of the Vicomte de Valmont played by John Malkovich in Stephen Frears’s adaptation, filmed in 1988, has Basslike qualities—his belief in the marriage of “love and revenge”; his love of cruelty, a word with “a noble ring”; his postcoital use of a woman’s bare ass as a writing desk. (“I have this appalling reputation, as you may know,” he purrs to the pious Madame de Tourvel, saying more or less the same thing as Chuck Bass is saying when he snarls his irritating catchphrase.) Still, our introduction to Chuck Bass—headed for school, and saying of a female character that “there’s something wrong with that level of perfection; it needs to be violated”—is soundtracked by Vivaldi’s gorgeous and frenetic Concerto alla Rustica, a choice that cannot help but bring to mind another oversexed, amoral bastard with a certain screen appeal. In All That Jazz, the same concerto accompanies Roy-Scheider-as-Fosse for his morning routine, smoking in the shower, beating off and popping pills, sitting in front of his mirror with an ever-escalating sense of the inevitability of decline. What results is a sense of hedonism in pursuit of death rather than pleasure, a suggestion of bored pessimism that turns out to suit Chuck Bass down to the ground.
The girl so perfect she must be violated is Serena van der Woodsen, a gold-plated human thoroughbred played by Blake Lively, who has recently returned to New York after spending some time hiding out at boarding school in Connecticut. Her best friend—and later Chuck’s lover and co-conspirator—is a brunette named Blair Waldorf who is played by Leighton Meester, and dresses like an American Girl doll whose ethnicity is “bitch.” Her high school boyfriend, an airheaded himbo by the name of Nate, is brought to sort-of-life by a blond actor named Chace Crawford, and Serena’s dorky love interest, attending private school despite not being one of the fully-elite kids, is a boy called Dan. Because the hollow-eyed and angular Penn Badgley happens to portray him, he does not look believably like a nerd at all, but like a fashion model dressed up as a geek. His sister, Jenny, is a fourteen-year-old blonde with a great many big ambitions, and no interesting story lines. She is played by Taylor Momsen, a young woman who eventually left Gossip Girl to front a metal band, appearing in a t-shirt emblazoned with I FUCK FOR SATAN despite obviously being a Catholic girl from St. Louis, Missouri.
The news, first announced last year, that Gossip Girl would be rebooted on HBO Max in 2020 (since postponed) is interesting in light of the fact that America’s tolerance for Vaseline-lensed rich-kid bullshit would appear to be significantly lower than in 2007, not to mention the fact that a former reality TV star with a net worth of $2.1 billion is the president incumbent. That it was once the most popular teen show on earth may be partly attributable to younger viewers’ love of watching other adolescents act like amoral adults, but it was also a matter of timing: premiering at more or less the same time as the inaugural season of Keeping Up with the Kardashians, Gossip Girl fed a growing hunger for dumb, aspirational programming that behaved like brainless, hyper-capitalist ASMR. Like KUWTK, too, it lacquers drama onto drama, tying up loose ends within a forty-minute period, then untying a few more in time for next week. Never mind that these rich brats’ spats, their nasty little Machiavellian games, are the same kind of spats and nasty little Machiavellian games that tend to land the rest of us poor, un-rich dopes in trouble when they’re played out in our governments, our banks, our major businesses. In Gossip Girl’s earliest episodes, watching these wealthy teenagers act out is like watching lion cubs play-fighting: yes, it’s possible that someday they may kill us, but not yet.
Putting the “opera” in “soap opera,” Gossip Girl’s six seasons play out as a melodrama where the petty and inconsequential squabbles inherent in young adult life are amplified by access to enormous wealth and privilege. In its first season, in addition to Chuck’s two attempted rapes, there is the revelation that Serena slept with Nate while he was meant to be saving himself for his beloved, Blair; that Serena’s brother has attempted suicide, and that he’s gay; that Blair is a former bulimic, and her father left her mother for another man; that Serena’s mother and Dan’s father used to date, and that although Serena’s mother used to want to be an art photographer, she took up marrying multimillionaires instead because it proved “more useful”; that Dan and Vanessa, his childhood best friend, have what is dramatically referred to as “a bit of a history,” despite both being sixteen; that Chuck hopes to win the respect of his distant father by opening an extremely-2007 burlesque club; that Blair eventually loses her virginity to him in the back of his family’s limousine, and instantly regrets it; that Serena used to have a drinking problem; that Nate’s dad, a cocaine addict, has been committing fraud; that Dan—who, I must stress, is sixteen—is a brilliant enough writer to be published by the New Yorker, in their nonexistent “Twenty Under Twenty” issue; and that a mysterious old friend of Serena’s named Georgina stalked and drugged and blackmailed her. Reporting all of this is Gossip Girl, a website voiced by Kristen Bell that churns out “news” pertaining to this one small group of rich kids, submitted anonymously by their peers.
Over the course of six seasons, these slime puppies develop into full-sized toxic beasts, making it infinitely harder to enjoy their merriment, or to fully appreciate the intricacies of their boring, boundless cruelty. Rich teens devoting their lives to the destruction of their peers is one thing; mothers, fathers, politicians and publishing moguls doing so is quite another. The rebooted Gossip Girl will, thank God, not be quite as dazzlingly, pure-cut-cocaine-white as its Waspier, Tory-Burch-ier predecessor. (“This time around,” executive producer Joshua Safran reassured an interviewer late last year, “the leads are nonwhite. There’s a lot of queer content on this show.”) Most of its characters still presumably have or desire money in eye-popping quantities, since if they didn’t how would it resemble Gossip Girl at all? One way to make the show more palatable to a 2020 audience, perhaps, would be to frame it as a pitch-black comedy à la Succession, underscoring the grotesquerie of these privileged children’s lives with a low, nihilistic note of the absurd. “Look, here’s the thing about being rich, okay?” the idiotic Tom tells the even-more-idiotic Cousin Greg in the first season of Succession, moments before they pay through the nose to enter a dead nightclub VIP room that contains no other Ps. “It’s fucking great. It’s like being a superhero, only better. You get to do what you want. The authorities can’t really touch you. You get to wear a costume, but it’s designed by Armani and it doesn’t make you look like a prick.” What makes the show work is the fact that it makes being rich look like it isn’t fucking great at all—it makes it look exhausting, miserable, nervy, transient and very, very hollow. “This class war shit,” the family’s only female sibling, Shiv Roy, asks, while scrolling through the news. “Don’t you find it a little jejune?” “A little jejune” is the perfect way to describe half her family. They are dense, self-interested and incapable of experiencing what regular, unwealthy people might describe as “joy.” Being even the most do-nothing of the Roys appears to be more complicated—less pleasurable, even—than having to work an actual nine-to-five.
The original run of Gossip Girl has as much backstabbing and underlying mistrust as Succession, but it does not have its fury, its black heart. If Succession is, as critics most often suggest, a modernized King Lear, then Gossip Girl’s literary parallel is Edith Wharton’s The Age of Innocence—not least because the kids of Constance and St. Jude’s put on a version of the play at school. “Before Gossip Girl, there was Edith Wharton,” Kristen Bell breathes in the introductory voiceover. “And how little has changed.” “They all lived in a kind of hieroglyphic world,” Wharton writes of New York’s high society of the 1870s. “The real thing was never said or done or even thought, but only represented by a set of arbitrary signs.” “He guessed himself to have been, for months, the centre of countless silently observing eyes and patiently listening ears,” she says of Newland Archer, who is being played by Dan in Gossip Girl’s high school production. “Archer felt like a prisoner in the centre of an armed camp.” The metaphor is a snug fit: the “countless silently observing eyes” are simply, in this instance, sending tips to Gossip Girl rather than seeding them in drawing rooms and theater boxes.
“What has always stuck in my head,” Martin Scorsese once recalled, explaining why he first chose to adapt The Age of Innocence, “is the brutality under the manners. People hide what they mean under the surface of language. In the subculture I was around when I grew up in Little Italy, when somebody was killed, there was a finality to it. It was usually done by the hands of a friend. And in a funny way, it was almost like ritualistic slaughter, a sacrifice. … But [this society] was so cold-blooded.”
Still, when Wharton’s spiky, elegant novel of manners was repurposed for the CW show, something ended up lost in the translation: a sense of the moral universe of Gossip Girl as one in which actions have serious, far-reaching consequences. Because even its substantial plotlines are designed to wrap up, telenovela-like, within a five-episode span at the very most, there is no sense of lasting peril: a love child appears in the last episode of Season Two, and disappears forever by the fifth of Season Three; Serena’s father is caught poisoning her mother, and the whole arc wraps up in just three hours of screen time. Each unhappy event has a swift, clean resolution, making it unclear exactly what the punishment is for committing a financial, criminal or sexual transgression if you happen to be born a Bass, a Waldorf or a van der Woodsen. Had Scorsese made a movie about the main characters of Gossip Girl, he would no doubt have let their worst trespasses marinate on screen, rather than flickeringly disperse. As it happens, what might have been terrifying is an irritant, instead: a rash left by a fake designer dress in lieu of actual injury.
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Four months before Gossip Girl first aired, a Canadian developer launched PornHub, the adult video-sharing website. To say that the widespread distribution of free, short-form video pornography helped to define the sexual attitudes of the ensuing decade would be something of an understatement; Gen Z teens, who have by now usually seen at least one video of a gang-bang sometime before turning twelve, are hard to scandalize. A chaste and primarily off-screen threesome where the third is Hilary Duff would no longer be wild enough to warrant teasing with the slogan “OMFG,” as it did when the scene aired on Gossip Girl in 2009. A show that depicted mostly-clothed teenagers having mostly consensual sex would no longer be “banned” in schools or proudly advertised as being “very bad for you.” Consider HBO’s high school drama Euphoria, which boasted not only a famous thirty penises, but thirteen-year-olds doing Oxy, pedophiles, amateur pornographers, kid drug dealers and repeated sexual choking. Released in 2019, its lead character was born just three days after 9/11, making it feel wedded to the weighty aftermath of that event in more or less the same way Gossip Girl feels situated in the weightless time before it. The line YA television has to cross before earning an OMFG has, suffice to say, since moved several light-years beyond seventeen-year-olds smoking a joint or ordering scotch.
Whether or not we were meant to like its characters, it is the case that its two female leads, Blair and Serena, came to represent a kind of Betty-or-Veronica division between girl fans. If Chuck Bass is Gossip Girl’s most interesting character, its second-best might be his on-again-off-again paramour, Blair, whose baby-doll attire and wardrobe of padded headbands belie an unsettling ruthlessness, a willingness to (metaphorically, hopefully) kill rather than be (metaphorically, hopefully) killed. “Damn that motherchucker,” she spits, a Miu-Miu-wearing Lady Macbeth whose substitute for a dagger is more often than not a witty bon mot. “That Chuck Basstard.” Blair exudes an air of cute hostility, as if she is a Persian kitten hissing; she is beautiful and rich but, crucially, unlike Serena she is brunette, and therefore painfully insecure. Although she is already technically Upper East Side royalty, she reveals herself to be manically obsessed with the idea of marrying into royalty proper, or at least into the aristocracy. Her other passion is Serena, with whom she is almost constantly at war, and whom she describes as her “best friend” with the same stoic admiration a general might afford his chief opponent. Picturing her in Season Six, Blair is both furious, and nearly swooning: “Blonde. Legs for days. Effortless charisma that only someone far less secure than I am would find threatening.”
Of Serena van der Woodsen’s two great passions, one is almost certainly herself. In Season Two, she ends up briefly in jail—ostensibly for the Lohanian crime of stealing an expensive bracelet—and as a result becomes famous, having had her mug shot published on the cover of the New York Post. “I just wish that they would leave me alone,” she whines about the paparazzi. “Oh, is that why you got your hair blown out?” coos Blair. She is photographed on Valentino’s yacht, and with Prince Harry doing shots off her bare breasts; at some point, trying to get away from the improbably named “Carter Baizen,” a rich playboy with whom several of the main characters have had tediously shady dealings, she hijacks a horse at a charity polo match. “Dropping your dress, stealing a horse,” he groans, seemingly unaware that he is uttering the series’ best line, “all it is is a cry for attention!” A nearby photographer captures an image of her on the horse, her blond hair somehow simultaneously wild and perfect: she wears a pale-peach silk gown, a frown so delicate it might be Fabergé. There is no moment in the show’s six seasons more Serena, nor more illustrative of her maddening, to-the-manor-born appeal.
If Gossip Girl has any hint of sadomasochistic love, it is as likely to be found in the relationship between Blair and Serena as it is, for instance, in the messed-up love affair Blair has with Chuck: the two girls’ blonde-and-brunette mirroring, the psychosexual intensity of their mutual obsession, is like something out of Bergman, Lynch or Hitchcock. (Interestingly, Meester claims to have been told at her audition to be “innocent and slutty, blonde and brunette,” which is surely more or less the same thing Hitchcock told Kim Novak when the two of them made Vertigo.)
Disappointingly, it never occurs to Blair and Serena that going to bed together, in lieu of serially sleeping with each others’ boyfriends, might end up being the sanest course of action. Instead, the hottest and heaviest head-to-head between the two girls is their battle for supremacy at interviews for admission to Yale. It turns out that although Blair has done the hard work, supplementing her enormous privilege with a near-sociopathic focus on her academic future, Serena is newly famous, and has great legs, making her the superior candidate for one of the best universities on earth. “Since we’re not friends anymore, let me speak frankly,” hisses Blair. “You’re not that smart. You lack focus and discipline.” None of these shortcomings are troubling to Yale, as long as Serena agrees to let them publicize her forthcoming attendance with a press release. (I need not point out the connection to the recent scandal involving numerous famous people and their undeserving children, but I can only assume some version of that story line will make the reboot. If the screenwriters are looking for a decent joke to crib from life, might I suggest the lawyer Felicity Huffman hired calling prison “the great leveler” for the ultra-wealthy?) “For people like us,” Chuck reminds Serena, “a college degree is just an accessory, like a Malawi baby or a poodle.” When he says “people like us,” he is invoking a Venn diagram made out of circles that say “rich kids,” “famous kids” and “hot kids.” At its best, Gossip Girl takes an interest in the minor differences between the social strata of the very, very wealthy, mining the relationship between cash, fame and privacy. Serena van der Woodsen becomes a celebrity because she is a socialite; the six kids at the center of the show are documented, paparazzi-style, by Gossip Girl for similar reasons.
The question of whether privilege and affluence ought to be paid for by a lack of privacy, a need for radical transparency and an unasked-for status as a public figure has been current for as long as we’ve had politicians, movie stars, socialites and royal families, and have also had a mainstream media. The half-decade spanned by Gossip Girl, covering the earliest years of Instagram and Twitter, ended up being perfectly timed with the new, shifting boundaries between celebrities and civilians, with its characters manipulating the titular website in more or less the same way famous people manipulate social media as a means of finessing their carefully curated images. Maybe the quaintest, most outdated thing about the show in retrospect is its depiction of teenagers whose one opportunity for recourse when it comes to altering their online narratives is to send in another contradictory tip to the Upper East Side’s merciless Blog Almighty.
“On a meta level,” Josh Duboff wrote in Vanity Fair in 2017, “the actors on the show were among the last wave of young television stars who were not broadcasting their every move on social media—which perhaps helped to create a certain air of mystery and intrigue about them, one that doesn’t exist in the same way for young television stars now.” It boggles the mind to imagine how the characters of Gossip Girl would deal with services like Instagram, in particular a proto-influencer like Serena van der Woodsen, whose photogenic features, basic tastes and enviable wardrobe could not be better designed for fit-tea sponcon. The show’s sort-of prescience about the pressures of a life projected online will be necessarily updated when it comes back on air, owing to the fact that now it is not only very rich or very famous people who find themselves daily at “the centre of countless silently observing eyes and patiently listening ears,” feeling like “a prisoner in the centre of an armed camp.”
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Speaking, as we were, of the dynamics of the internet: one thing that Gossip Girl gets right in its original incarnation is the identity of its final villain. Dan, a self-identified “nice guy” with an astounding victim complex, is a gorgeous white boy with a moderately famous dad. He attends an exclusive high school; he dates several very beautiful, very expensive-looking women; and at some point his father marries the ex-wife of a billionaire with no apparent prenup. Despite this, he sees himself as a perennial outsider, angst-ridden, furiously railing at the status quo and channeling all this fury into what the show would like us to interpret as his Art.
From the second season through to the finale, Gossip Girl places a dreadful, baffling focus on the image of Dan Humphrey as a literary boy-genius, beginning with an improbable story line in which the Paris Review begs him for a story about Chuck. Being a literary boy genius, Dan decides to give his character the alias “Charlie Trout.” We are given a rare, tantalizing glimpse of the teen maestro’s work when he submits it, a brief excerpt of which I include below:
His hand held a firm grip around the glass Scotch [sic]. It was like the glass was a part of him and if he let it go he’d lose a piece of himself. He took one long gulp and finished off the glass.
“Keep them coming, Joe,” he spoke across the bar. The surly bartender poured some more of the brown liquid into his glass. He tilted it towards Joe and took a sip. As it hit his mouth, his lips curled around it and he swallowed. The glass was still in his hand.
Dan is in many ways, ironically, already the ideal caricature of a young author for a 2020 reboot: online-savvy, untalented, a writer of autobiographical faux-fiction, sired by a famous rock star and likely to look amazing in a photo shoot for SSENSE. He writes a novel, Inside, in the penultimate season; it concerns his immediate friend group, and is modeled on the YA series on which Gossip Girl is based. The book, which is first leaked anonymously, and then published with Simon & Schuster to much critical acclaim, is described as “a little Wharton, and a lot Wolfe.” “A searing portrait of Manhattan’s elite, with just the right portion of pathos,” raves the New York Times. When Dan hands in the manuscript for a possible sequel, he includes a little outline of Manhattan on the front like it’s Sex and the goddamned City.
The image of Dan as a mortifying arriviste—a man as obsessed with these people as he is with his supposed socioeconomic distance from them—forms slowly over the course of the show, culminating in the deranged revelation that the titular gossiping girl is, in fact, Dan. This means that Dan first spread the rumor that Serena had an STD; that he penned an extensive blog post speculating on the loss of his sister’s virginity; that he has deliberately sabotaged his own relationship with his immediate family, as well as most of his friends’ romantic relationships. Most egregiously of all, he gave himself the drippy nickname “Lonely Boy.”
Even those involved with the series were not entirely thrilled with what was ultimately seen by audiences as a nonsensical, left-of-field development. “I like to joke that Dan was Gossip Girl because I had left the show by then,” Joshua Safran shrugged in 2019. “Dan was not my intended Gossip Girl.” “I still am not sure who GG was lol,” Ed Westwick told Vanity Fair in an email in 2017, in a piece pegged to the program’s ten-year anniversary. (Also included with the article: a photograph of Jared Kushner and Ivanka Trump, who had cameos on the show, engaged in conversation with Blake Lively and Penn Badgley “at a gala at Cipriani Wall Street in October 2008.” “I think I’m a cross between Blair Waldorf and Lily van der Woodsen when it comes to the style,” Ivanka has observed.)
If Chuck Bass—with his womanizing and his sexual assaults, his Daddy’s money and his devil’s absent morals—is Trumpian in his crimes and his biography, Dan is a Trumpian character in his tireless need for validation from his peers, and his astounding adeptness at manipulating other people’s narratives for his own benefit. The difference is that, like Jay Gatsby, he has done it all for love: “Every writer needs his muse,” he insists, despite having called Serena, in one of the chapters from his second novel, Inside Out, a “golden shell.” “The Upper East Side was like something from Fitzgerald or Thackeray,” he tells the group whose lives he has been laying bare for several years in the finale:
Teenagers acting like adults, adults acting like teenagers: guarding secrets, spreading gossip, all with the trappings of truly opulent wealth. And membership in this community was so elite you couldn’t even buy your way in. It was a birthright … All I had to compare to this world was what I’d read in books. But that gave me the idea. If I wasn’t born into this world, maybe I could write myself into it.
Publishing Inside Out in installments at the Spectator, he has been leaking new, salacious autofiction about his immediate peers over the season’s last few episodes, alienating everyone he cares about in quick succession. Because crying “fake news” as a means of distancing oneself from the literal truth did not become an option for wealthy, high-profile, gossip-prone Americans until 2016, everything Dan ascribes to his horrified peers in Inside Out is taken to be gospel. “Are they talking about how the use of real names makes this my In Cold Blood?” he wonders, hopefully, in exile after dropping the first of his literary grenades. This is the second invocation of Truman Capote’s work in Gossip Girl, suggesting that the series’ writers are familiar with the entry in his bibliography that hews the closest to Dan’s documents of dubious class strife: the serialization of Capote’s own salacious work of autofiction, Answered Prayers, in Esquire magazine in 1975. Like Dan, Capote was not born into the one percent; like Dan, he became close to several beautiful, well-bred society women, only to mine their embarrassments for literary material. “When that bullet is fired from the gun,” Capote said gleefully about the release of his first installment, “it’s going to come out with a speed and power like you’ve never seen—wham!” Wham, indeed: Capote talked up Answered Prayers as his potential magnum opus, foolishly believing that his subjects would be too dumb to discern themselves beneath his pseudonyms, or so forgiving they’d accept being sacrificed for art. He ended up blindsided by their opprobrium and shut out of upscale New York.
Where other, saner people might have cut out Dan forever for his machinations, the core friendship group in Gossip Girl see it as proof that he is truly one of them, a sociopath whose ambitions outweigh his sympathy for human suffering. Like Capote, Dan is both the scammer and the scammed, a kind of male Caroline Calloway seduced by an uninteresting, bankrupt ruling class. The final episode is like the end of Orwell’s Animal Farm, the viewer glancing—figuratively speaking—between pig and man, and man and pig, and being unable to discern a difference. Serena agrees to marry Dan; in the finale, in a flash-forward, the group attend their wedding. Nate, arguably the stupidest character in Gossip Girl, ends up in politics. Chuck and Blair, both of whom have spent the last five years alternately screwing each other and screwing each other over, have a child. It is supposedly a happy ending.
“We make our own fortunes,” Gossip Girl says in a voiceover about halfway through Season Three, “and call them fate.” Technically, these kids inherited their fortunes; it is true, however, that the vibe of Gossip Girl is not exactly one of fairy-tale predestination. While the show might hint at the idea that what keeps its six leads entwined in-universe is kismet, an alembic of desire and destiny, above all else what really ties them to each other is their wealth: birds of an economic feather flock—and fight, and fuck—together. (When, in Season One, Gossip Girl’s voiceover observes that “whoever thought monarchy was dead didn’t realize it just changed ZIP codes,” it could easily be making reference to the very, very small sexual and genetic pool that its characters swim in, Habsburgian in its intimacy.) Its most deeply entrenched bonds are not familial or emotional, but fiscal. “The rich people I know,” Capote once wrote, “would be totally lost if they didn’t have their money. That’s why … they hang together so closely like a bunch of bees in a beehive.” “It’s fucking crazy,” a deadpan Penn Badgley told New York in 2013. “It’s impossible. I mean, those six people—why do they even keep hanging out?”
What might Gossip Girl in 2020 look like, given what we know about its previous failures, its outmoded facets and its more interesting, prescient touches? The 2007 show is watchable only if viewers are capable of either overlooking or embracing its insanity, sinking into the madness like a bath of warmed-up Veuve Clicquot. Its newer incarnation faces several possibilities. When shopping Answered Prayers, Capote billed the book as “a dark comedy of the very rich,” which is effectively the angle I suggested earlier when I invoked Succession: crueler, stripped of levity and more aware of the social and economic doom wrought by its protagonists’ class, it might appeal to an adult audience rather than a teen one, and might earn a life outside millennial nostalgia. It might have been fascinating to see it get remade as a period piece set in 2007—a more nakedly post-9/11 show made about an earlier, dreamier version of New York, its style and soundtrack now a pastiche rather than an aspirational fantasy—although the brief synopsis that’s available unfortunately makes it clear that this won’t happen. “Eight years after the original website went dark,” Deadline reports, “a new generation of New York private school teens are introduced to the social surveillance of Gossip Girl. The prestige series will address just how much social media—and the landscape of New York itself—has changed in the intervening years.”
“Man hands down inhumanity to man,” as someone even more highly regarded in the field of literature than Dan once wrote. “It deepens like a coastal shelf.” Savage and Schwartz have already confirmed that in the series reboot, there will be no characters who are literally the descendants of Dan, Blair, Serena, Nate or Chuck—“we’re not that old!” Schwartz told reporters, mock-horrified—although it hardly matters, given the way that the one percent beget the one percent, an ironclad dynasty in secretiveness and in bad behavior if not necessarily in blood. In the first season of Succession, the Roy family’s therapist ends up reciting the first lines of that Philip Larkin poem, the joke being that its message—that your parents “fuck you up”—is simultaneously idiotic in its obviousness, banal in its suitability and understated in its characterization of exactly how far the Roy children have been irretrievably destroyed. He does not recite the last verse, which suggests that the one way to escape pain is to avoid reproducing altogether. Gossip Girl, with its early adoption of extreme “social surveillance” and its bratty, privileged kids, is certainly a parent in its own way to a micro-generation of millennials, glued to their phones and half-ironically enraptured by the empty lives of better-looking, richer people. Who can say what to expect of its actual bastard child, other than more of the same inherited cruelty?
As played by Ed Westwick, Chuck Bass is a sybaritic little monster, the son of a billionaire, and arguably the most compelling character in Gossip Girl. He has the haircut and the daddy issues and entirely the mien of Joaquin Phoenix’s pissy, pouting boy-emperor Commodus in the movie Gladiator, and he has a catchphrase—“I’m Chuck Bass,” a kind of personal mantra whose intended purpose is to reassure him of his own importance, and whose actual purpose is to reassure the audience that he’s an asshole. Like the other main characters in the show, Bass is a student at an elite private high school, but behaves as if he is a forty-year-old villain from a movie about Wall Street. He drinks scotch, dresses like an even preppier Patrick Bateman, and regular one-on-one sex will not do for him if there is any possibility of sweet-talking his way into a threesome, or a foursome. There is something to be said about his being born on third and hitting it in triplicate, but I am hesitant to be the one to formulate the joke.
In the pilot episode, he also tries to rape two separate women. It seems crucial to explain this upfront, partly because Gossip Girl itself does not make much of an attempt to make sense of it in its later episodes, and partly because of all of the series’ twists and turns, it is the one that seems truest to life. Both times, it is entirely conceivable that rather than a rapist, Bass sees himself as a particularly strident seducer of women, aiming to bestow on them the invaluable gift of his sixteen-year-old sexual prowess. Both times, it is also clear to even the most casual viewer that what’s happening is assault. When you’re the son of a billionaire, I wrote inevitably in my notes, they let you do it. You can do anything. Grab ’em by the pussy. If Chuck was sixteen in 2007, when the first season of Gossip Girl is set, I calculated that by 2029, he could be president.
Created by Josh Schwartz and Stephanie Savage, who in 2007 were best known for The O.C., Gossip Girl is tonally bizarre; it is a teen romp, dazzlingly staged, whose characters are as amoral and unpleasant as fully-grown gangsters. Where The O.C. was Californian enough that the locale inspired not only the title but the theme tune, Gossip Girl was deeply New York: cocky, jaded, swift and mean, and full of kids who had grown up entirely too fast.
The showrunners of Gossip Girl have often talked about drawing their inspiration from Dangerous Liaisons, with Chuck Bass effectively functioning as a modernized Vicomte de Valmont. Certainly, the version of the Vicomte de Valmont played by John Malkovich in Stephen Frears’s adaptation, filmed in 1988, has Basslike qualities—his belief in the marriage of “love and revenge”; his love of cruelty, a word with “a noble ring”; his postcoital use of a woman’s bare ass as a writing desk. (“I have this appalling reputation, as you may know,” he purrs to the pious Madame de Tourvel, saying more or less the same thing as Chuck Bass is saying when he snarls his irritating catchphrase.) Still, our introduction to Chuck Bass—headed for school, and saying of a female character that “there’s something wrong with that level of perfection; it needs to be violated”—is soundtracked by Vivaldi’s gorgeous and frenetic Concerto alla Rustica, a choice that cannot help but bring to mind another oversexed, amoral bastard with a certain screen appeal. In All That Jazz, the same concerto accompanies Roy-Scheider-as-Fosse for his morning routine, smoking in the shower, beating off and popping pills, sitting in front of his mirror with an ever-escalating sense of the inevitability of decline. What results is a sense of hedonism in pursuit of death rather than pleasure, a suggestion of bored pessimism that turns out to suit Chuck Bass down to the ground.
The girl so perfect she must be violated is Serena van der Woodsen, a gold-plated human thoroughbred played by Blake Lively, who has recently returned to New York after spending some time hiding out at boarding school in Connecticut. Her best friend—and later Chuck’s lover and co-conspirator—is a brunette named Blair Waldorf who is played by Leighton Meester, and dresses like an American Girl doll whose ethnicity is “bitch.” Her high school boyfriend, an airheaded himbo by the name of Nate, is brought to sort-of-life by a blond actor named Chace Crawford, and Serena’s dorky love interest, attending private school despite not being one of the fully-elite kids, is a boy called Dan. Because the hollow-eyed and angular Penn Badgley happens to portray him, he does not look believably like a nerd at all, but like a fashion model dressed up as a geek. His sister, Jenny, is a fourteen-year-old blonde with a great many big ambitions, and no interesting story lines. She is played by Taylor Momsen, a young woman who eventually left Gossip Girl to front a metal band, appearing in a t-shirt emblazoned with I FUCK FOR SATAN despite obviously being a Catholic girl from St. Louis, Missouri.
The news, first announced last year, that Gossip Girl would be rebooted on HBO Max in 2020 (since postponed) is interesting in light of the fact that America’s tolerance for Vaseline-lensed rich-kid bullshit would appear to be significantly lower than in 2007, not to mention the fact that a former reality TV star with a net worth of $2.1 billion is the president incumbent. That it was once the most popular teen show on earth may be partly attributable to younger viewers’ love of watching other adolescents act like amoral adults, but it was also a matter of timing: premiering at more or less the same time as the inaugural season of Keeping Up with the Kardashians, Gossip Girl fed a growing hunger for dumb, aspirational programming that behaved like brainless, hyper-capitalist ASMR. Like KUWTK, too, it lacquers drama onto drama, tying up loose ends within a forty-minute period, then untying a few more in time for next week. Never mind that these rich brats’ spats, their nasty little Machiavellian games, are the same kind of spats and nasty little Machiavellian games that tend to land the rest of us poor, un-rich dopes in trouble when they’re played out in our governments, our banks, our major businesses. In Gossip Girl’s earliest episodes, watching these wealthy teenagers act out is like watching lion cubs play-fighting: yes, it’s possible that someday they may kill us, but not yet.
Putting the “opera” in “soap opera,” Gossip Girl’s six seasons play out as a melodrama where the petty and inconsequential squabbles inherent in young adult life are amplified by access to enormous wealth and privilege. In its first season, in addition to Chuck’s two attempted rapes, there is the revelation that Serena slept with Nate while he was meant to be saving himself for his beloved, Blair; that Serena’s brother has attempted suicide, and that he’s gay; that Blair is a former bulimic, and her father left her mother for another man; that Serena’s mother and Dan’s father used to date, and that although Serena’s mother used to want to be an art photographer, she took up marrying multimillionaires instead because it proved “more useful”; that Dan and Vanessa, his childhood best friend, have what is dramatically referred to as “a bit of a history,” despite both being sixteen; that Chuck hopes to win the respect of his distant father by opening an extremely-2007 burlesque club; that Blair eventually loses her virginity to him in the back of his family’s limousine, and instantly regrets it; that Serena used to have a drinking problem; that Nate’s dad, a cocaine addict, has been committing fraud; that Dan—who, I must stress, is sixteen—is a brilliant enough writer to be published by the New Yorker, in their nonexistent “Twenty Under Twenty” issue; and that a mysterious old friend of Serena’s named Georgina stalked and drugged and blackmailed her. Reporting all of this is Gossip Girl, a website voiced by Kristen Bell that churns out “news” pertaining to this one small group of rich kids, submitted anonymously by their peers.
Over the course of six seasons, these slime puppies develop into full-sized toxic beasts, making it infinitely harder to enjoy their merriment, or to fully appreciate the intricacies of their boring, boundless cruelty. Rich teens devoting their lives to the destruction of their peers is one thing; mothers, fathers, politicians and publishing moguls doing so is quite another. The rebooted Gossip Girl will, thank God, not be quite as dazzlingly, pure-cut-cocaine-white as its Waspier, Tory-Burch-ier predecessor. (“This time around,” executive producer Joshua Safran reassured an interviewer late last year, “the leads are nonwhite. There’s a lot of queer content on this show.”) Most of its characters still presumably have or desire money in eye-popping quantities, since if they didn’t how would it resemble Gossip Girl at all? One way to make the show more palatable to a 2020 audience, perhaps, would be to frame it as a pitch-black comedy à la Succession, underscoring the grotesquerie of these privileged children’s lives with a low, nihilistic note of the absurd. “Look, here’s the thing about being rich, okay?” the idiotic Tom tells the even-more-idiotic Cousin Greg in the first season of Succession, moments before they pay through the nose to enter a dead nightclub VIP room that contains no other Ps. “It’s fucking great. It’s like being a superhero, only better. You get to do what you want. The authorities can’t really touch you. You get to wear a costume, but it’s designed by Armani and it doesn’t make you look like a prick.” What makes the show work is the fact that it makes being rich look like it isn’t fucking great at all—it makes it look exhausting, miserable, nervy, transient and very, very hollow. “This class war shit,” the family’s only female sibling, Shiv Roy, asks, while scrolling through the news. “Don’t you find it a little jejune?” “A little jejune” is the perfect way to describe half her family. They are dense, self-interested and incapable of experiencing what regular, unwealthy people might describe as “joy.” Being even the most do-nothing of the Roys appears to be more complicated—less pleasurable, even—than having to work an actual nine-to-five.
The original run of Gossip Girl has as much backstabbing and underlying mistrust as Succession, but it does not have its fury, its black heart. If Succession is, as critics most often suggest, a modernized King Lear, then Gossip Girl’s literary parallel is Edith Wharton’s The Age of Innocence—not least because the kids of Constance and St. Jude’s put on a version of the play at school. “Before Gossip Girl, there was Edith Wharton,” Kristen Bell breathes in the introductory voiceover. “And how little has changed.” “They all lived in a kind of hieroglyphic world,” Wharton writes of New York’s high society of the 1870s. “The real thing was never said or done or even thought, but only represented by a set of arbitrary signs.” “He guessed himself to have been, for months, the centre of countless silently observing eyes and patiently listening ears,” she says of Newland Archer, who is being played by Dan in Gossip Girl’s high school production. “Archer felt like a prisoner in the centre of an armed camp.” The metaphor is a snug fit: the “countless silently observing eyes” are simply, in this instance, sending tips to Gossip Girl rather than seeding them in drawing rooms and theater boxes.
“What has always stuck in my head,” Martin Scorsese once recalled, explaining why he first chose to adapt The Age of Innocence, “is the brutality under the manners. People hide what they mean under the surface of language. In the subculture I was around when I grew up in Little Italy, when somebody was killed, there was a finality to it. It was usually done by the hands of a friend. And in a funny way, it was almost like ritualistic slaughter, a sacrifice. … But [this society] was so cold-blooded.”
Still, when Wharton’s spiky, elegant novel of manners was repurposed for the CW show, something ended up lost in the translation: a sense of the moral universe of Gossip Girl as one in which actions have serious, far-reaching consequences. Because even its substantial plotlines are designed to wrap up, telenovela-like, within a five-episode span at the very most, there is no sense of lasting peril: a love child appears in the last episode of Season Two, and disappears forever by the fifth of Season Three; Serena’s father is caught poisoning her mother, and the whole arc wraps up in just three hours of screen time. Each unhappy event has a swift, clean resolution, making it unclear exactly what the punishment is for committing a financial, criminal or sexual transgression if you happen to be born a Bass, a Waldorf or a van der Woodsen. Had Scorsese made a movie about the main characters of Gossip Girl, he would no doubt have let their worst trespasses marinate on screen, rather than flickeringly disperse. As it happens, what might have been terrifying is an irritant, instead: a rash left by a fake designer dress in lieu of actual injury.
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Four months before Gossip Girl first aired, a Canadian developer launched PornHub, the adult video-sharing website. To say that the widespread distribution of free, short-form video pornography helped to define the sexual attitudes of the ensuing decade would be something of an understatement; Gen Z teens, who have by now usually seen at least one video of a gang-bang sometime before turning twelve, are hard to scandalize. A chaste and primarily off-screen threesome where the third is Hilary Duff would no longer be wild enough to warrant teasing with the slogan “OMFG,” as it did when the scene aired on Gossip Girl in 2009. A show that depicted mostly-clothed teenagers having mostly consensual sex would no longer be “banned” in schools or proudly advertised as being “very bad for you.” Consider HBO’s high school drama Euphoria, which boasted not only a famous thirty penises, but thirteen-year-olds doing Oxy, pedophiles, amateur pornographers, kid drug dealers and repeated sexual choking. Released in 2019, its lead character was born just three days after 9/11, making it feel wedded to the weighty aftermath of that event in more or less the same way Gossip Girl feels situated in the weightless time before it. The line YA television has to cross before earning an OMFG has, suffice to say, since moved several light-years beyond seventeen-year-olds smoking a joint or ordering scotch.
Whether or not we were meant to like its characters, it is the case that its two female leads, Blair and Serena, came to represent a kind of Betty-or-Veronica division between girl fans. If Chuck Bass is Gossip Girl’s most interesting character, its second-best might be his on-again-off-again paramour, Blair, whose baby-doll attire and wardrobe of padded headbands belie an unsettling ruthlessness, a willingness to (metaphorically, hopefully) kill rather than be (metaphorically, hopefully) killed. “Damn that motherchucker,” she spits, a Miu-Miu-wearing Lady Macbeth whose substitute for a dagger is more often than not a witty bon mot. “That Chuck Basstard.” Blair exudes an air of cute hostility, as if she is a Persian kitten hissing; she is beautiful and rich but, crucially, unlike Serena she is brunette, and therefore painfully insecure. Although she is already technically Upper East Side royalty, she reveals herself to be manically obsessed with the idea of marrying into royalty proper, or at least into the aristocracy. Her other passion is Serena, with whom she is almost constantly at war, and whom she describes as her “best friend” with the same stoic admiration a general might afford his chief opponent. Picturing her in Season Six, Blair is both furious, and nearly swooning: “Blonde. Legs for days. Effortless charisma that only someone far less secure than I am would find threatening.”
Of Serena van der Woodsen’s two great passions, one is almost certainly herself. In Season Two, she ends up briefly in jail—ostensibly for the Lohanian crime of stealing an expensive bracelet—and as a result becomes famous, having had her mug shot published on the cover of the New York Post. “I just wish that they would leave me alone,” she whines about the paparazzi. “Oh, is that why you got your hair blown out?” coos Blair. She is photographed on Valentino’s yacht, and with Prince Harry doing shots off her bare breasts; at some point, trying to get away from the improbably named “Carter Baizen,” a rich playboy with whom several of the main characters have had tediously shady dealings, she hijacks a horse at a charity polo match. “Dropping your dress, stealing a horse,” he groans, seemingly unaware that he is uttering the series’ best line, “all it is is a cry for attention!” A nearby photographer captures an image of her on the horse, her blond hair somehow simultaneously wild and perfect: she wears a pale-peach silk gown, a frown so delicate it might be Fabergé. There is no moment in the show’s six seasons more Serena, nor more illustrative of her maddening, to-the-manor-born appeal.
If Gossip Girl has any hint of sadomasochistic love, it is as likely to be found in the relationship between Blair and Serena as it is, for instance, in the messed-up love affair Blair has with Chuck: the two girls’ blonde-and-brunette mirroring, the psychosexual intensity of their mutual obsession, is like something out of Bergman, Lynch or Hitchcock. (Interestingly, Meester claims to have been told at her audition to be “innocent and slutty, blonde and brunette,” which is surely more or less the same thing Hitchcock told Kim Novak when the two of them made Vertigo.)
Disappointingly, it never occurs to Blair and Serena that going to bed together, in lieu of serially sleeping with each others’ boyfriends, might end up being the sanest course of action. Instead, the hottest and heaviest head-to-head between the two girls is their battle for supremacy at interviews for admission to Yale. It turns out that although Blair has done the hard work, supplementing her enormous privilege with a near-sociopathic focus on her academic future, Serena is newly famous, and has great legs, making her the superior candidate for one of the best universities on earth. “Since we’re not friends anymore, let me speak frankly,” hisses Blair. “You’re not that smart. You lack focus and discipline.” None of these shortcomings are troubling to Yale, as long as Serena agrees to let them publicize her forthcoming attendance with a press release. (I need not point out the connection to the recent scandal involving numerous famous people and their undeserving children, but I can only assume some version of that story line will make the reboot. If the screenwriters are looking for a decent joke to crib from life, might I suggest the lawyer Felicity Huffman hired calling prison “the great leveler” for the ultra-wealthy?) “For people like us,” Chuck reminds Serena, “a college degree is just an accessory, like a Malawi baby or a poodle.” When he says “people like us,” he is invoking a Venn diagram made out of circles that say “rich kids,” “famous kids” and “hot kids.” At its best, Gossip Girl takes an interest in the minor differences between the social strata of the very, very wealthy, mining the relationship between cash, fame and privacy. Serena van der Woodsen becomes a celebrity because she is a socialite; the six kids at the center of the show are documented, paparazzi-style, by Gossip Girl for similar reasons.
The question of whether privilege and affluence ought to be paid for by a lack of privacy, a need for radical transparency and an unasked-for status as a public figure has been current for as long as we’ve had politicians, movie stars, socialites and royal families, and have also had a mainstream media. The half-decade spanned by Gossip Girl, covering the earliest years of Instagram and Twitter, ended up being perfectly timed with the new, shifting boundaries between celebrities and civilians, with its characters manipulating the titular website in more or less the same way famous people manipulate social media as a means of finessing their carefully curated images. Maybe the quaintest, most outdated thing about the show in retrospect is its depiction of teenagers whose one opportunity for recourse when it comes to altering their online narratives is to send in another contradictory tip to the Upper East Side’s merciless Blog Almighty.
“On a meta level,” Josh Duboff wrote in Vanity Fair in 2017, “the actors on the show were among the last wave of young television stars who were not broadcasting their every move on social media—which perhaps helped to create a certain air of mystery and intrigue about them, one that doesn’t exist in the same way for young television stars now.” It boggles the mind to imagine how the characters of Gossip Girl would deal with services like Instagram, in particular a proto-influencer like Serena van der Woodsen, whose photogenic features, basic tastes and enviable wardrobe could not be better designed for fit-tea sponcon. The show’s sort-of prescience about the pressures of a life projected online will be necessarily updated when it comes back on air, owing to the fact that now it is not only very rich or very famous people who find themselves daily at “the centre of countless silently observing eyes and patiently listening ears,” feeling like “a prisoner in the centre of an armed camp.”
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Speaking, as we were, of the dynamics of the internet: one thing that Gossip Girl gets right in its original incarnation is the identity of its final villain. Dan, a self-identified “nice guy” with an astounding victim complex, is a gorgeous white boy with a moderately famous dad. He attends an exclusive high school; he dates several very beautiful, very expensive-looking women; and at some point his father marries the ex-wife of a billionaire with no apparent prenup. Despite this, he sees himself as a perennial outsider, angst-ridden, furiously railing at the status quo and channeling all this fury into what the show would like us to interpret as his Art.
From the second season through to the finale, Gossip Girl places a dreadful, baffling focus on the image of Dan Humphrey as a literary boy-genius, beginning with an improbable story line in which the Paris Review begs him for a story about Chuck. Being a literary boy genius, Dan decides to give his character the alias “Charlie Trout.” We are given a rare, tantalizing glimpse of the teen maestro’s work when he submits it, a brief excerpt of which I include below:
Dan is in many ways, ironically, already the ideal caricature of a young author for a 2020 reboot: online-savvy, untalented, a writer of autobiographical faux-fiction, sired by a famous rock star and likely to look amazing in a photo shoot for SSENSE. He writes a novel, Inside, in the penultimate season; it concerns his immediate friend group, and is modeled on the YA series on which Gossip Girl is based. The book, which is first leaked anonymously, and then published with Simon & Schuster to much critical acclaim, is described as “a little Wharton, and a lot Wolfe.” “A searing portrait of Manhattan’s elite, with just the right portion of pathos,” raves the New York Times. When Dan hands in the manuscript for a possible sequel, he includes a little outline of Manhattan on the front like it’s Sex and the goddamned City.
The image of Dan as a mortifying arriviste—a man as obsessed with these people as he is with his supposed socioeconomic distance from them—forms slowly over the course of the show, culminating in the deranged revelation that the titular gossiping girl is, in fact, Dan. This means that Dan first spread the rumor that Serena had an STD; that he penned an extensive blog post speculating on the loss of his sister’s virginity; that he has deliberately sabotaged his own relationship with his immediate family, as well as most of his friends’ romantic relationships. Most egregiously of all, he gave himself the drippy nickname “Lonely Boy.”
Even those involved with the series were not entirely thrilled with what was ultimately seen by audiences as a nonsensical, left-of-field development. “I like to joke that Dan was Gossip Girl because I had left the show by then,” Joshua Safran shrugged in 2019. “Dan was not my intended Gossip Girl.” “I still am not sure who GG was lol,” Ed Westwick told Vanity Fair in an email in 2017, in a piece pegged to the program’s ten-year anniversary. (Also included with the article: a photograph of Jared Kushner and Ivanka Trump, who had cameos on the show, engaged in conversation with Blake Lively and Penn Badgley “at a gala at Cipriani Wall Street in October 2008.” “I think I’m a cross between Blair Waldorf and Lily van der Woodsen when it comes to the style,” Ivanka has observed.)
If Chuck Bass—with his womanizing and his sexual assaults, his Daddy’s money and his devil’s absent morals—is Trumpian in his crimes and his biography, Dan is a Trumpian character in his tireless need for validation from his peers, and his astounding adeptness at manipulating other people’s narratives for his own benefit. The difference is that, like Jay Gatsby, he has done it all for love: “Every writer needs his muse,” he insists, despite having called Serena, in one of the chapters from his second novel, Inside Out, a “golden shell.” “The Upper East Side was like something from Fitzgerald or Thackeray,” he tells the group whose lives he has been laying bare for several years in the finale:
Publishing Inside Out in installments at the Spectator, he has been leaking new, salacious autofiction about his immediate peers over the season’s last few episodes, alienating everyone he cares about in quick succession. Because crying “fake news” as a means of distancing oneself from the literal truth did not become an option for wealthy, high-profile, gossip-prone Americans until 2016, everything Dan ascribes to his horrified peers in Inside Out is taken to be gospel. “Are they talking about how the use of real names makes this my In Cold Blood?” he wonders, hopefully, in exile after dropping the first of his literary grenades. This is the second invocation of Truman Capote’s work in Gossip Girl, suggesting that the series’ writers are familiar with the entry in his bibliography that hews the closest to Dan’s documents of dubious class strife: the serialization of Capote’s own salacious work of autofiction, Answered Prayers, in Esquire magazine in 1975. Like Dan, Capote was not born into the one percent; like Dan, he became close to several beautiful, well-bred society women, only to mine their embarrassments for literary material. “When that bullet is fired from the gun,” Capote said gleefully about the release of his first installment, “it’s going to come out with a speed and power like you’ve never seen—wham!” Wham, indeed: Capote talked up Answered Prayers as his potential magnum opus, foolishly believing that his subjects would be too dumb to discern themselves beneath his pseudonyms, or so forgiving they’d accept being sacrificed for art. He ended up blindsided by their opprobrium and shut out of upscale New York.
Where other, saner people might have cut out Dan forever for his machinations, the core friendship group in Gossip Girl see it as proof that he is truly one of them, a sociopath whose ambitions outweigh his sympathy for human suffering. Like Capote, Dan is both the scammer and the scammed, a kind of male Caroline Calloway seduced by an uninteresting, bankrupt ruling class. The final episode is like the end of Orwell’s Animal Farm, the viewer glancing—figuratively speaking—between pig and man, and man and pig, and being unable to discern a difference. Serena agrees to marry Dan; in the finale, in a flash-forward, the group attend their wedding. Nate, arguably the stupidest character in Gossip Girl, ends up in politics. Chuck and Blair, both of whom have spent the last five years alternately screwing each other and screwing each other over, have a child. It is supposedly a happy ending.
“We make our own fortunes,” Gossip Girl says in a voiceover about halfway through Season Three, “and call them fate.” Technically, these kids inherited their fortunes; it is true, however, that the vibe of Gossip Girl is not exactly one of fairy-tale predestination. While the show might hint at the idea that what keeps its six leads entwined in-universe is kismet, an alembic of desire and destiny, above all else what really ties them to each other is their wealth: birds of an economic feather flock—and fight, and fuck—together. (When, in Season One, Gossip Girl’s voiceover observes that “whoever thought monarchy was dead didn’t realize it just changed ZIP codes,” it could easily be making reference to the very, very small sexual and genetic pool that its characters swim in, Habsburgian in its intimacy.) Its most deeply entrenched bonds are not familial or emotional, but fiscal. “The rich people I know,” Capote once wrote, “would be totally lost if they didn’t have their money. That’s why … they hang together so closely like a bunch of bees in a beehive.” “It’s fucking crazy,” a deadpan Penn Badgley told New York in 2013. “It’s impossible. I mean, those six people—why do they even keep hanging out?”
What might Gossip Girl in 2020 look like, given what we know about its previous failures, its outmoded facets and its more interesting, prescient touches? The 2007 show is watchable only if viewers are capable of either overlooking or embracing its insanity, sinking into the madness like a bath of warmed-up Veuve Clicquot. Its newer incarnation faces several possibilities. When shopping Answered Prayers, Capote billed the book as “a dark comedy of the very rich,” which is effectively the angle I suggested earlier when I invoked Succession: crueler, stripped of levity and more aware of the social and economic doom wrought by its protagonists’ class, it might appeal to an adult audience rather than a teen one, and might earn a life outside millennial nostalgia. It might have been fascinating to see it get remade as a period piece set in 2007—a more nakedly post-9/11 show made about an earlier, dreamier version of New York, its style and soundtrack now a pastiche rather than an aspirational fantasy—although the brief synopsis that’s available unfortunately makes it clear that this won’t happen. “Eight years after the original website went dark,” Deadline reports, “a new generation of New York private school teens are introduced to the social surveillance of Gossip Girl. The prestige series will address just how much social media—and the landscape of New York itself—has changed in the intervening years.”
“Man hands down inhumanity to man,” as someone even more highly regarded in the field of literature than Dan once wrote. “It deepens like a coastal shelf.” Savage and Schwartz have already confirmed that in the series reboot, there will be no characters who are literally the descendants of Dan, Blair, Serena, Nate or Chuck—“we’re not that old!” Schwartz told reporters, mock-horrified—although it hardly matters, given the way that the one percent beget the one percent, an ironclad dynasty in secretiveness and in bad behavior if not necessarily in blood. In the first season of Succession, the Roy family’s therapist ends up reciting the first lines of that Philip Larkin poem, the joke being that its message—that your parents “fuck you up”—is simultaneously idiotic in its obviousness, banal in its suitability and understated in its characterization of exactly how far the Roy children have been irretrievably destroyed. He does not recite the last verse, which suggests that the one way to escape pain is to avoid reproducing altogether. Gossip Girl, with its early adoption of extreme “social surveillance” and its bratty, privileged kids, is certainly a parent in its own way to a micro-generation of millennials, glued to their phones and half-ironically enraptured by the empty lives of better-looking, richer people. Who can say what to expect of its actual bastard child, other than more of the same inherited cruelty?
If you liked this essay, you’ll love reading The Point in print.