The Internet’s Greatest Grifter: On Caroline Calloway’s “Scammer”
Caroline Calloway | Scammer | Dead Dad Press | June 2023 | 206 Pages
Caroline Calloway can run but she can’t dance. It’s because she has no kneecaps, having had them removed as “the youngest person in the history of all mankind to have a double patellectomy.” This is just one of the many exciting claims made by the It-Girl / lapsed Instagram influencer from Falls Church, Virginia, in her recently self-published memoir, Scammer, which reads like an immersive Adderall experience, cycling frenetically between vignettes of grief, addiction, clout-chasing, and point-scoring that are always chaotic and sometimes brilliant.
It’s difficult for me to express how loath I am to insert the requisite biographical paragraph here, because simply put, if you know about Caroline Calloway, you know everything. In the broadest of strokes, she was a pioneer of influencer culture on Instagram, turning purchased followers into real followers through canny marketing moves, transforming photos of her life in New York and later Cambridge into an alluring personal brand of ivy towers and ball gowns with paid posts on highly-visible accounts before targeted ads were even a thing, and expertly-honed captions, which she was then able to parlay into a major book deal that she later reneged. The captions are at the heart of the matter: In 2019 The Cut published a longform-bombshell essay by a writer named Natalie Beach, dishing the dirt on the complicated friendship she had with Calloway and staking the claim that she was behind great swathes of the internet celebrity’s online writings. The article went viral, breaking Calloway out of her mostly YA-adjacent online fandom and earning her notoriety, or infamy depending on your position, in New York’s media scrum. Ultimately, the personal essay earned Beach her own major book deal. This heralded Calloway’s scammer era: she hawked a face serum called “Snake Oil” alongside decorative “grift” (not gift) cards, paid back her publisher’s advance with the money she made from what she called “cerebral softcore porn” on OnlyFans, and avoided paying rent on her West Village studio apartment for about a year. Scammer, in large part, is an accounting of those years, rushed to press to coincide with the publishing of Natalie Beach’s book of essays Adult Drama.
As a memoir of grief and addiction—Calloway’s father was found dead just days after The Cut article dropped—Scammer is unflinching. There are tender evocations of living with a father suffering from mental illness, a man who graduated from Harvard in his teens and ended his days on a blood and vomit-soaked mattress in a house overfilled with tchotchkes, that are followed with unequivocal observations: when the police take away her father’s dead body, they don’t clean the scene, and Calloway pulls a living maggot from the mattress, wondering if she too is a kind of maggot, “feeding off tragedy while the real victim’s dead.” Her growing dependence on prescription amphetamines is punctuated with amusing anecdotes about the dodgy West Village doctor who provides her with the coveted orange pills and the kind of outrageous behavior that becomes normal in addicts: she flew from the UK to New York City every month to ensure her supply of drugs, cadging money for the flights any way she could.
Reading Calloway on the ins and outs of nascent influencer culture is illuminating, if at times disconcerting: she conflates the idea of It-Girls with start-ups, and posits that coins from the Late Bronze Age were the first form of social media, little pieces of art that had monetary value and circulated freely in society. There’s her dating grift in Sarasota, Florida, where she moved to finish her book: before she swore off men for women, she would match with “Florida Men” on dating apps and have them take her to the nicest bistro in town, where they ended up paying for her $19 “scamburger.” The book is composed of 67 vignettes, a mysterious number, (a nod to the Knight of Pentacles, perhaps?) and it is difficult to discern any pattern in the way they are structured and ordered. All the same, they frequently catch fire with a surprising turn of phrase: going online sounds like “a telephone fucking a fax machine;” Swedish girls with flowers in their hair ignore Caroline and chatter away in their “lilting alley-oop gibberish.”
In an otherwise energetic book, it’s during Calloway’s revisiting of the minutiae of the “extremely online” pitched battles for which she first became famous that the writing loses muscle mass. Her explanations of what exactly happened at her ill-fated Creativity Workshops and why, along with her version of who wrote which captions and when, somehow manage to come across as baroque and coy at the same time, and in any case, for those steeped in the lore—at $65 per personalized edition of this book, that’s probably close to one hundred per cent of the readership—these are issues that have long since been litigated in the kangaroo courts of Twitter.
I missed out on the experience of Scammer as bespoke objet d’art—when I asked Calloway for a galley over Twitter she responded with “My precious king. Hit me with your email address and I’ll sort you right out” then had her talent manager email me a watermarked PDF—so I missed out on the artisanal charms of the book and its seafoam blue packaging, but was left with the minor vexations of self-publishing. There are plenty of typos and omissions, including in the “About the Author” note, but not more than you might find in a book put out by a university press. What is lacking is an intuitive editorial presence, or at least a functional copy edit (“typos are her brand,” after all). Experimental punctuation and stodgy metaphors abound—“we’ve already drank in the poison like fish because the patriarchy is an ocean, and its hate is the water we swim through every day just trying to exist”—and there’s an over-reliance on the exclamation point, which is intended to be ecstatic or perhaps Byronic, but instead gives off a jittery “No worries if not!!” energy. Writers are responsible for their own sentences, but there might have been a more inspired choice for an editor out there than Mike “Crumps” Crumplar, known for blogging about Dimes Square and the Urbit-meets-literary scene on Substack, a medium notorious for its lack of editorial oversight. Lily Anolik’s profile of Caroline Calloway for Vanity Fair is a major part of the book, which is disorienting, because the profile was meant to accompany the book’s publication.
The lowest ebbs of the book come in the treatment of Natalie, with whom Calloway had one of those relationships of Sapphic-sisterly intensity in early adulthood, as they goaded each other on in David Lipsky’s nonfiction workshop at NYU, trying on elements of each other’s identity, experiencing things for the first time together. Calloway is frank about the extent to which this friendship has soured and the urgency of this publication: “Over my fucking dead body would Natalie put out a book before I did,” which unfortunately, is the north star of the project. There are constant references to the workman-like quality of Beach’s prose, a dollop of body shaming, a strange daydream sequence in which Calloway fantasizes about aiming an arrow at Beach’s heart, then her neck, before letting it fly just wide of the mark, and the author’s honest recounting of how her “cunt clenched with desire” as Beach first told her of being sexually assaulted. Calloway would later re-enact the assault with her Swedish boyfriend.
This kind of radical honesty is part of the contract with the reader when it comes to memoir, and it’s something for which women writers routinely face the kind of scrutiny men skate right past—consider the radically different reception of parenting memoirs by Karl Ove Knausgaard and Rachel Cusk, for example—but it can also embolden unsavory criticism that has more to do with the writer than the writing. Elizabeth Wurtzel, whose influence haunts nearly every page of this book, is a case in point: contemporary reviews of her memoir Prozac Nation were a masterclass in misogyny. There’s also the question of genre itself: there’s an established tradition in American letters of privileging storytelling over truth-telling when it comes to what we might call literary journalism. Writers from Joseph Mitchell through Gay Talese to David Foster Wallace (“DFW” earns a couple of mentions in Scammer) have been accused of creating composite characters, smoothing out timelines or padding out stories with unfact-checkable details, all in service of either a better story or an emotional truth. Throughout Scammer, Calloway’s assertions that she had always wanted to be a memoirist struck me as odd, coming from someone whose persona and writing has always been a curlicue of reality and fantasy. But in the final pages of the book she provides her own justification, an honest desire to be seen, heard, and understood: “I became a memoirist in the first place because I don’t know who I am unless my memories are shared; agreed upon. Beloved beyond me. But perhaps the antidote to shame is exposure. Accepting who we are is the price for who we will become.”
But to borrow a phrase from this memoir’s cultural Weltanschauung, I couldn’t help but wonder: what if Caroline Calloway had turned her talents toward the novel? The very same charges leveled against writers like Wurtzel, or Calloway—narcissism, vanity, unchecked ambition—are precisely the qualities that have enshrined Undine Spragg and Becky Sharp as peerless literary heroines. Unfettered from the tyranny of agreed-upon memories, Calloway has enough lived experience, or “plot cocaine,” as she calls it, and writing nous for a cracking social novel, one that could push beyond the mere recounting of what happened and into a Vanity Fair of the twenty-first century.
So, then, what’s the grift in Scammer? If anything, Calloway is operating a low-key matrix scheme, a scam similar to a pyramid scheme from the dot com boom where an individual pays money to be added to a waiting list, and maybe receives a token gift while waiting to move up the order. All too often in Scammer, Calloway takes us right to the precipice of a juicy scene, a moment where the memoir might come alive with the presence of others besides the character of Caroline Calloway. But that’s when she reminds us that Scammer is in fact just a prelude to And We Were Like, which will be “the real book” recounting her life to date. It’s a cheeky move, but not without literary precedent: describing a work of genius without having to put it on the page has been used by figures as diverse as Marcel Proust, Roberto Bolaño, and Jack Black. Caroline Calloway’s Scammer returns, ouroboros-like, to the image of Cézanne’s apples, a piece of artwork somehow more lifelike than life itself, the condition to which all great art aspires, and maybe that’s what we can expect from her next book.