FROM THE MAGAZINE

Caroline Calloway Survived Cancellation. Now She’s Doubling Down

From topless literary performances on OnlyFans to her homegrown “Snake Oil” and “grift” card business, “The Scammer”—as Caroline Calloway titles herself in a new memoir—is back.
Caroline Calloway with her cat Matisse.
THE ORCHID THIEF Caroline Calloway, photographed in her Sarasota, Florida, home with her cat, Matisse. Dress by Cecilie Bahnsen; ring (left hand, middle finger) by The One I Love NYC.Photograph by Martin Schoeller; Styled by Samantha Gasmer.

It’s 10 a.m. on a Monday, early February, and I’m stepping off a plane in Sarasota, Florida. I’ve come to visit Caroline Calloway, scandalous internet celebrity. (“Scandalous internet celebrity” is what I’m tagging her with now because I have to tag her with something, and it’s accurate if inadequate. Tagging her properly is, you could say, the point of this entire piece.) 

A short Uber ride takes me to a building that’s very clearly a retirement home though not explicitly billed as such. No one in the lobby or on the grounds is a day under 80. Lots of bright white sneakers and denim pantsuits. I hold the elevator for a woman with a walker who wants to show me the package she’s just received from QVC. 

I exit the elevator and there’s Calloway, framed in the doorway of her condo, one foot forward, the other back. She’s 31 but looks like a girl, like Alice in Wonderland: small and slender with smooth, honey-hued skin; a precisely molded forehead, chin, and mouth; large, clear eyes. She has an armful of cat, stuffed, I think at first, only realizing my error when it slow-blinks at me before turning away in feline disdain. A ribbon ties back her long hair, brown, though somehow not, somehow giving the impression of fairness, blondness. Her clothes are plain yet stylish—oversized white oxford, fitted blue shorts, blue flats.

How you know she’s Caroline Calloway and not Alice in Wonderland: her press-on nails, long and painted, a different theme for each nail, the theme for her thumbnail a fiery car crash. Calloway is a writer but one better known for what she hasn’t written than what she has. It’s the Instagram captions she wrote in 2014 and 2015 about her life as a bright-eyed American undergraduate among a glamorous and decadent elite at Cambridge University that made her (Instagram) famous. It’s School Girl, a book that was supposed to be an extension of those Cambridge captions, a book she never wrote, though she signed a contract worth half a million dollars to do so, that made her—started to make her—(real-world) infamous. In any case, she has a nonfiction writer’s eye for vivid detail. So I’m certain the nail is a vivid detail she’s planted. She means for me to pick up on it, include it here. 

As she bends over to reposition the cat, her breast—the left one—is briefly exposed. That she’s without a bra in a shirt unbuttoned almost to her navel is also a vivid detail. It too might be planted. After all, she made her breasts part of the public discourse when, in 2020, she opened an OnlyFans account in order, she claimed, to pay back the advance for School Girl. And maybe she’s flashing me now so I won’t forget to mention that she was, for a period, the purveyor of what she termed “cerebral softcore porn.” (Translation: She dressed up as famous female characters in literature, except topless. Daisy Buchanan, topless. Juliet Capulet, topless. Arwen—“the hot elf in Lord of the Rings, the one Liv Tyler played,” she explained at my bewildered look—topless.)

Or maybe she’s just behind on her laundry.

Calloway and I have been talking for a year and a half, but this is only our second in-person meeting, so instead of hugging her, I say hi. She raises the cat’s paw in greeting, then scampers off. From another room, she calls out that she’s trying to find the bellhop cap she bought Matisse. (Matisse is the cat.)

While I wait for her to come back, I wander inside—the moment I remember the words my friend Mitchell, who is also Calloway’s friend Mitchell, said last night. He knew I was interviewing her at her condo this morning and wanted to prepare me for what I was about to see. “It’s Instagram Grey Gardens,” he told me.

VIBE SHIFTY Calloway burns sage by a portrait of her ancestor. Clothing by Batsheva; shoes by Manolo Blahnik; earrings and rings (right hand, ring finger; left hand, middle finger) by The One I Love NYC.Photograph by Martin Schoeller; Styled by Samantha Gasmer.

He’s right, I think, looking around. That’s exactly what Calloway’s condo is, only Calloway’s condo is actually Calloway’s grandmother’s condo. Or was until Calloway’s grandmother died last June. Calloway had moved in after moving out of her apartment—a studio in Manhattan’s West Village—in the spring. She was staying to help take care of her grandmother. Then, when her grandmother no longer required caretaking, she was staying to pack up her grandmother’s things. She was also staying just to stay since she’d sublet (illegally) the West Village apartment to Rachel Rabbit White, former sex worker and poet, and White’s husband, convicted bank robber and novelist Nico Walker.

Everything about the condo is musty fusty old-lady: the furnishings, the fixtures, the smells. But then overlaying the musty fusty is the “girly bohemian chaos” Calloway prides herself on. Scattered across the dark wood surfaces of antique tables and nightstands and armoires are Glossier products, Diptyque candles, arts and crafts supplies, a MetroCard, mismatched earrings, real flowers in glass vases, fake flowers in glass Coke bottles. On a doily, a bottle of antidepressants (Fluoxetine). In front of a dollhouse, a bottle of anti-anxiety meds (Gabapentin). On the bookshelf, intermingled with her grandmother’s movie-star memoirs—Lauren Bacall’s By Myself and Then Some, Myrna Loy’s Being and Becoming—her reality-star and YouTuber memoirs—Audrina Patridge’s Choices: To the Hills and Back Again, Stassi Schroeder’s Next Level Basic: The Definitive Basic B*tch Handbook, PewDiePie’s This Book Loves You.

​I crouch down to better examine the workstation Calloway has set up on the carpet. She’s assembling packages of “Grift (not gift) Cards,” an inside joke between her and her fans. In early 2019, she went viral as a grifter for launching a national “creativity workshops” tour that failed, rather spectacularly, to come off. She forgot to book venues; promised “mason jar gardens,” then, after 1,200 jars were delivered, had nowhere to put them; promised “orchid crowns” but only managed a single measly non-orchid flower per attendee; etc.

Months later, she went viral again as a different kind of grifter when her former best friend and NYU classmate Natalie Beach wrote an exposé for The Cut. In it, Beach claimed that she was Calloway’s ghostwriter: editor of the Instagram captions, cowriter of the School Girl proposal. “I Was Caroline Calloway” was an absolute sensation, The Cut’s most read story of 2019. (“It was supposed to come out the day Jeffrey Epstein died,” says Beach. “But fact-checking took so long that it got pushed back a month. You get lucky with how things hit and when.”) By the end of the year, Calloway was all-the-way infamous—a grifter two times over; canceled for being a grifter two times over. 

Calloway, back with Matisse, looking très sportif in his bellhop cap, stops in front of a gilt-edged mirror to confirm her prettiness. She smiles at her reflection, the smile spilling onto me as she turns. We talk for a few minutes about how her lawsuit is going. (In March of last year, the landlord of that West Village apartment accused her of skipping out on $40,000 in back rent.) When she’d first informed me of the financial pickle she was in, she’d said, widening her eyes, “At a certain point, I realized I could either live luxuriously or pay my rent.” A statement so dumb, it’s funny. I remind her of it now with a laugh.

Instead of laughing back, she nods gravely and says, “Yeah, I made a choice. Honestly, I’m not even sure it was the wrong choice. The underlying humor is like, ‘Ha, ha, and I regret it.’ But do I? A bank wouldn’t have given me a loan with that low an interest rate to go party like a princess.” (She and her landlord have come to an understanding, she says: She’ll pay him $5,000 a month until she reaches $40,000, throwing in an additional $5,000 to cover his legal expenses.) 

She chews her bottom lip as she thinks. “I’m often reductive about myself in a jokey way. Like, ‘Oh, 40 grand to party.’ But it was an opportunity. I didn’t know when we’d see again the white-hot molten center of what’s cool in downtown New York embracing cancel culture in the ways that it did in the summer of 2021. It was a pop-culture lunar eclipse that I wanted to take advantage of. I’ve created a brand out of thin air. I’m a business. But banks don’t see me that way. Nothing but writing a book could ever make me a writer, but being there, with the right people in the right places having the right conversations, could make me in a much better position culturally for when my book did come out. And being there took money. I want to be an It girl. It girls are start-ups, and start-ups need funding.”

I’m so astounded by the whole speech, the last line in particular, that all I can do is stare. Calloway does this frequently: Right at the moment I’ve condescended to her, she knocks me flat by offering an insight both radical and renegade in that sweet-girl voice of hers, high and bright and harmless. And then I remember: She looks like Edie Sedgwick, thinks like Andy Warhol. Is a living, breathing contradiction in terms, and my response to her is contradictory. 

The writing on which she built her reputation, the Cambridge captions and the School Girl proposal—think Daisy Miller crossed with The Princess Diaries; think Brideshead Revisited but coed—I don’t like. It’s wish fulfillment for adolescent and postadolescent girls of the slurpiest, most trivial sort. It stirs my imagination not at all. And my official reaction to her stories is rejection.

My unofficial reaction to her stories, however, is rapture. Not the stories she writes, the ones about castles, gowns, garden parties, and impossibly handsome young men all bucking for the title of Prince Charming, which are silly shit and kid stuff and old-fashioned. The stories she tells, the ones about engagement rates, hashtags, clout fucking, and Dimes Square—about making it in America in the first quarter of the 21st century—which are serious shit and grown-up and wildly, emphatically contemporary.

Calloway on how she mastered Instagram:

“I got my Instagram handle in 2012. The app was up-and-coming. A typical post was an aerial shot of avocado toast and, for a caption, hashtag ‘Valencia.’ That Dior would one day hire Instagrammers to cover its shows, or that The New York Times would break news on Instagram in tandem with the website was unthinkable. It was in January 2013, after Cambridge accepted me, after I dropped out of NYU, that I really started investing in Instagram. I bought 40,000 followers for maybe $4.99, which makes me sound like”—she breaks into a mincing parody of an old person—“ ‘I remember when soda pop was a nickel.’

“I knew I wanted not just followers but readers, and not just any readers but readers who were predisposed to become obsessed with what they read. I targeted book fandom accounts—Harry Potter, The Hunger Games—and bought ads. So, I spent all of my savings on this, plus more of my dad’s money, which I would later learn he didn’t even have. I’d buy a package of 10 posts for $50, which sounds insane. But the thing is, the people I bought the ads from thought I was insane, that I was throwing away money. And they were like, ‘Oh, are you sure?’ Then I would take every ounce of my ability as a writer to study the way they wrote their captions. When they liked something, did they say it was ‘awesome’ or ‘amazing’? What emojis did they use? How many exclamation points? I would write the ads in the voice of the account owner so that they didn’t look like ads, they looked like captions. 

Now the FTC has rules about that, but not then. And I’d be like, ‘I found the most amazing new account, her stories are so great.’ I’d time these little ad campaigns to go up just as I was posting original stories on my own account. And that’s how I started to get real followers.”

Calloway on how she survived getting canceled the first time after the creativity workshop fiasco:

“The rules that apply to surviving a riptide apply to surviving getting canceled. Your first instinct is to struggle. You want to clear your name, set the record straight. Don’t. If you do, you’ll expend your energy too quick and drown. What you do instead is follow the current, even if the last thing you want to do is go in the direction public opinion is carrying you. If you’re me, that means leaning into your scammer identity. You don’t point out that you offered everyone a refund. Or that the people the workshop was meant for actually had a good time. No, you name your next book Scammer. And then, once the undertow subsides, you can make your way back to shore.”

Calloway on how she survived getting canceled the second time after the “I Was Caroline Calloway” fiasco:    

“Natalie stole my identity with that piece. We did write captions together in the beginning, when we were writing for an audience of no one—for bots. But my first two years at Cambridge, we barely spoke. I alone wrote the captions that got me real followers, that got me fame. And then we wrote the book proposal together, half her words, half mine, because I was too high on Adderall to do it myself. Natalie was never my ghostwriter. A few years later, I got an email from her. She told me she’d written about our friendship and that I’d be hearing from a fact-checker. There are a lot of things that I give myself credit for anticipating correctly. When I imagined how many stories would come from the piece, how many press miles, I almost nailed it. I knew it would be life-changing. What I didn’t know was that Natalie would utilize this regressive, misogynistic model of beauty equals dumb, ugly equals smart. But it wasn’t all bad for me. Listen, if you’ve never had any scandals, my advice would be to continue to have none. But if you’ve had one, have as many more as you can. It’s the Kardashian, Trumpian information overload fatigue. There’s a point where people can’t retain enough information to remember every little scandal. Whereas if you have one scandal, people remember, and it defines you.”

I’m still recovering from the “It girls are start-ups” line, my mouth hanging open as if on a hinge, when she suggests we begin the interview. With effort, I close my mouth and nod, follow her to the front of the condo.

We’re sitting on what Calloway refers to as the lanai, a word I’ve never heard outside of a Golden Girls rerun. She’s written something she wants to read to me, is scrolling through her laptop to find it. I await with interest.

It isn’t quite true that I reject her writing. It’s the pre-cancellation writing that I reject. Six months after Beach’s tell-all dropped, Calloway posted on her website “I Am Caroline Calloway,” a novella-length essay. She called it a response to Beach, but really it was the latest version of the Caroline Calloway story. The first version, the Cambridge captions, was the story told as a YA fairy tale. The second version, “I Was Caroline Calloway,” was the story retold as a gritty bildungsroman. According to Beach, the real Caroline Calloway wasn’t Caroline Calloway, a magnetic beauty whose life was a series of madcap adventures that demonstrated again and again the world’s inability to say no to her. Rather, the real Caroline Calloway was Natalie Beach, a smart and unhappy plain Jane, ignored by men when she wasn’t brutalized by them. In one scene, Beach recounted a sexual assault. An older guy took her for drinks, then to bed, where he choked her and hit her without her consent. The de facto takeaway: She was the brains behind Caroline Calloway; Calloway merely the body. 

In “I Am Caroline Calloway,” Calloway is retelling the story yet again, this time as a lesbian gothic: the subtext of “I Was Caroline Calloway” made text. This version is about sexual repression and psychological vampirism and the domination of one personality by another—first Calloway’s by Beach’s, then Beach’s by Calloway’s. It’s also about addiction. (Beach, Calloway claims, turned her on to Adderall. “If Caroline says I introduced her to Adderall, she’s not making that up,” says Beach. “It’s a guilt and anxiety that I carry knowing how much she’s struggled with that drug.”) It’s about the fear of inherited madness as well. (Calloway’s father died by suicide, his decomposing corpse discovered in her childhood home in Falls Church, Virginia, two days after “I Was Caroline Calloway” went viral. In the second half of “I Am Caroline Calloway,” she does a literary exegesis of his autopsy report. “The medical examiner’s office still found living in his chest cavity a colony of maggots,” she writes.)

“I Am Caroline Calloway” isn’t without flaw, but it’s a mature work, dark and raw and powerful.

Calloway, unable to find what she’s looking for, shuts her laptop and just starts talking, telling me her plans. She’s been full of them for months now. Why she’s galvanized: the announcement that Adult Drama, a book of personal essays by Beach, will be published by Hanover Square Press in June.

Calloway on her initial reaction: “The first night I didn’t do anything. I just tried to sit with my feelings. Guess what? Didn’t work. Next night, absolute bender. I drink two bottles of wine. I’m super hungry, so I just start hitting up Hinge for someone who’ll take me out for what I refer to in my mind as a scamburger. I basically ask everyone on Hinge if they’ve tried hamburgers at this one spot where the hamburgers are like $20—not a cheap hamburger, but I’m not kept up at night for making them spend 20 bucks on me. It’s a good moral medium. So I find someone, a guy in a polka-dot shirt. He tries to go home with me, but I’m not feeling it. And I’m like, ‘You know what? I’m going to hook up with a girl. I’ve never hooked up with a girl, but I’m just going to go find a girl at a bar and take her home.’ And do you know what I do instead? I take home a guy who looks like Henry VIII—same belly, same beard, same haircut. Hooking up with a girl almost felt like a treat and this felt like a punishment.”

Calloway’s original plan was to do nothing. “I stay completely quiet, cut off Natalie’s oxygen source. Her book only works if I’m around and present and making headlines.” A solid plan but quickly discarded. Too low-key, I suspect. Too un-splashy.

Her plan—the opposite of low-key, ultra-splashy—is to self-publish the “Internet Trilogy,” bam, bam, bam: Scammer, which is “about 2019” (or was about 2019 when she first announced it in 2019) and which has been available for preorder since January 2020, will come out on March 23; I Am Caroline Calloway, an expanded version of the essay, on May 5; The Cambridge Captions, self-explanatory, on May 16. “I’d cap it at a thousand copies,” she tells me, “so that I could then resell and get an advance from publishers so they could have the mainstream rights.” She’ll finance the trilogy, she says, by peddling Grift (not gift) Cards; Snake Oil, her skin care product; Caro Cards—just like tarot cards but different—and other similarly themed merchandise for sale on her website. 

Scammer she’s dedicating to Lena Dunham, who wrote a script after Paramount optioned her life rights back in 2019. The option, though, has expired. “The names Caroline Calloway and Lena Dunham are doused in internet gasoline,” says Calloway. “All you need is a match. Even the dedication will be a minor news story. Also, what else can I do to get this movie made except dedicate my book to her?” I Am Caroline Calloway she’ll dedicate to Greta Gerwig; and The Cambridge Captions to Sofia Coppola. “I’ve decided I want three movies about my life,” she says.

Clothing by Des Phemmes; ring (right hand, ring finger) by The One I Love NYC.Photograph by Martin Schoeller; Styled by Samantha Gasmer.

I’m nodding encouragingly at her but with a sick sinking feeling in my stomach. It used to be that all the plans she constructed, no matter how pie-in-the-sky, she made happen. She thought she belonged on the big screen and so climbed up there with Daniel Craig and Nicole Kidman, delivering her single line—“Sir, this was on our roof”—with conviction in 2007’s The Invasion. (“Yes, I was a child actor—a key piece of my villain origin story.”) She likewise thought she belonged at Cambridge University, got in on her third try. (“I couldn’t live the rest of my life with an NYU email address.”) The name her parents gave her at birth, Caroline Gotschall, didn’t fit her conception of herself, which is why at 17 she swapped it for a name that did. (“I decided Caroline Calloway would look better on the cover of a book.”) She believed she could use the social networking service known as “Twitter for people who can’t read,” i.e. Instagram, to score a book contract and scored one with Flatiron. (“The US deal was for $375,000, but foreign deals brought that number up to just over $500,000.”)

Then in 2017, she took to Instagram to declare that she was withdrawing from her contract because she’d changed her mind about writing School Girl, now called And We Were Like. “I promised a memoir where the only thing that happened to me were boyfriends,” she said in a 2018 interview. “It wasn’t long before I realized the boy-obsessed version of myself I planned to depict as my memoir’s protagonist was not one I could stand behind.” She was spinning her renege as a bid for integrity, and perhaps it was. But she was also in the throes of a debilitating Adderall addiction. (She’s since stopped using. Adderall at least. “I don’t take uppers anymore,” she says. “Well, I do a little bit of coke. A holiday amount of coke, you know? Like, I don’t do coke more days in the year than there are holidays.”) And there might have been something else going on as well.

She continued to make plans after 2017, yet, one by one, they’ve sputtered, conked out. There’s a Reddit thread created by SMOLBEANSNARK dedicated to tracking and annotating her Instagram posts about Scammer. She’s blamed holdups variously on the return of her mother’s cancer, excessive partying, solidarity with Black Lives Matter. Shipping dates have come and gone many times. On November 8, 2020, she vowed that Scammer would be “AT LEAST 400 pages, more likely 450.” (Flash forward: One month after my Sarasota visit, I receive a text. “Scammer update: It’s taking shape before my eyes into more a book of 65 prose poems than a ‘memoir.’ ” Second flash forward: As of the printing of this issue, Scammer has not yet shipped. Neither has I Am Caroline Calloway, nor Cambridge Captions.)

Calloway is still talking, and as I watch her mouth move, the realization dawns: Natalie Beach, c’est moi.

Beach isn’t who I want to be. That, though, is who Calloway has turned me into. First of all, she makes disinterested journalism impossible. You can’t stay detached. She simply won’t allow it.

For example, a few weeks ago, over Zoom, I was listening to her read out loud a paragraph she’d written: “For months, I let a pool boy who is also a plumber fuck me without a condom. I haven’t used a condom in years.”

Unable to help myself, I interrupt. “You should stop having sex without a condom.”

She looks up at me, looks down, then gives a small shake of her head. “Oh,” she says. “No.”

I sigh.

For another example, over a different Zoom, I notice that she keeps pausing to suck on a lemon wedge. I ask her what she’s doing. She’s just taken mushrooms, she explains, and the lemon enhances the mushroom’s potency. I express irritation because I’d blocked out two hours for this interview, and now she was going to be too high to answer questions. No, no, she assures me, she won’t be too high to answer questions. Five minutes later she whispers, “I’m too high to answer questions.” I sigh.

She can be sweet and funny and charming, yet she has no respect for boundaries, personal or professional. In the middle of a conversation, she’ll fasten her eyes on mine, say breathily, “I’ve always thought I’d meet a journalist that I’d be friends with. I really hope it’s you.” Last March, she randomly sent me a video of herself getting ready to go out for the night. She was wearing a minidress and kept flipping it up, flashing her Red Scare thong, and doing this obscene darting thing with her tongue. My sons, then nine and seven, were constantly stealing my phone to watch.

If I continue talking to her, researching her, writing this piece on her, I’ll end up scrubbing the period blood out of her comforter, same as Beach. (Well, Beach didn’t scrub the blood-stained comforter, but she did stash it.) 

Really, though, Natalie Beach, c’est moi because Calloway makes me her collaborator. She needs one more than anybody I’ve ever met. There’s an air of purgatory about her. She’s been locked in a moment for six years, the moment she broke the contract with Flatiron. She’s doomed to try to write the book and fail to write the book over and over. She gives the book different titles—And We Were Like, Scammer, I Am Caroline Calloway—but it’s all, I’m convinced, the same book because it’s all the same story, the only story she has to tell: hers. And yet, for some mysterious reason, she can’t tell it. Not by herself, anyway.

How Calloway makes you her collaborator: She does cold reads on people. Is doing them on me all the time. Is alert to what I’m responsive to and then goes from there. 

For instance, she knows I like “I Am Caroline Calloway.” And once I call it a lesbian gothic, she starts calling it that too. I ask her if she’s going to change it substantially when she turns it into a book, and she says that she wants to make it “more of a lesbian gothic.” I point out that that’ll be tricky since she and Beach weren’t actually physically involved. She nods thoughtfully. “I’m sure there’s a way to write this, and that way might just be me fucking saying it, but Natalie’s sexual assault story—she actually didn’t tell the full extent of it in The Cut.

She checks to see if she has my attention. When she sees she does, she continues:

“Natalie called me out of the blue, crying, even though we hadn’t spoken in months. I just sat down on the sidewalk because I was so sad for her. I remember being interrupted because people kept being like, ‘Caroline, are you okay?’ No one just sits down on the ground in England. The thing is, I’m such a good crisis friend. It’s something that, especially during my addict years, I really doubled down on because I knew I was dropping the daily ball. I wasn’t returning texts or asking friends, ‘How are you?’ And it was great because I was awake for three days at a time. People could call at any hour and I’d pick up. When Natalie was talking, I was high on Adderall, and I wanted to speak so badly. But I was quiet. That was one of the only times I was a good friend to her during all those years.”

Calloway then proceeds to tell me the same disturbing story that Beach told readers, with a few additional lurid details. Perhaps the most lurid detail of all: that Calloway wasn’t disturbed by the disturbing story. At least, she wasn’t only disturbed by it.

“I’m thinking that there’s something really sad about it but also fucked up and hot,” says Calloway. “I’m with someone. It’s very trusting, lovey-dovey. I say to him, ‘Okay, I’m going to get blackout drunk. Let me be very clear with you about what I want.’ And then he did to me some of what that guy did to Natalie. I never told Natalie that.”

So, if Calloway never quite manages to get her revised lesbian gothic into book form, she sort of does because I’ve put it in this piece. Her new version is out there, and the new version—a fourth version of the Caroline Calloway story—feels like one we wrote together even though I had no clue that’s what we were doing. Which makes me yet another worker bee on the Caroline Calloway hive project.

As Beach was with “I Was Caroline Calloway,” is again with Adult Drama. 

As Darren Star is. (He figured out how to write the big pop commercial Caroline-in-Cambridge book, only he wrote it as a TV show and the young woman is called Emily and she’s in Paris.) 

As Ryan Murphy will be if he adapts Beach’s piece. (According to rumor, he snapped up the rights for a whopping million dollars.)

As Dunham will be if she ever films the script she wrote.

As Gerwig and Coppola will be if Calloway succeeds in turning their heads with her dedications.

Writers whose books are released by name publishing houses, whose pieces appear in name magazines, are, for the most part, bourgeois professionals, integrated into mainstream society. Calloway isn’t. She’s authentically on the outside and in opposition. Is, in other words, authentically avant-garde. Is also, I believe, authentically criminal. I don’t mean criminal in the literal or legal sense. (I seriously doubt she’s broken any major laws. The comparisons to Elizabeth Holmes and Anna Delvey always struck me as not just wrongheaded but flat-out wrong.) I mean criminal in the sense that she doesn’t do things on the up and up. The way she “gamed” Instagram is the way she “gamed” Cambridge University. (“I lied on my application,” she says. “I forged my transcript when I got in.”) And there’s an improvisatory recklessness to how she conducts her life that’s both thrilling and frightening. Like it’s all one big spree.

Dress by Sportmax; earrings by Presley Oldham. Throughout: hair products by Wella Professionals; makeup products by Danessa Myricks Beauty.Photograph by Martin Schoeller; Styled by Samantha Gasmer.

The term I’m groping for is con artist, emphasis on the artist because she’s authentically that too. It could be argued that she isn’t a writer but a performance artist’s take on a writer. Look at all the fascinating things she’s done with her failure to finish a book. There’s her foray into porn—paying off her publishers by desecrating the classics!—a desperate move, though also a witty and subversive one. There’s the “FACTS” section of her lawyer’s response to her landlord’s suit that’s written not in legalese, but Calloway-ese. (“Ms. Calloway had a very troubled childhood, which is why she spent so much money and time making improvements to the property—because 205 [West 13th Street] was not only her favorite home, but also her first.”) There’s the Reddit thread she inspired, which reads like Pale Fire for the internet age. And then there’s her feud with Beach, featherweight yet bloodthirsty, and the only game in town since literary types have gotten so milquetoast.

Beach, who understands what it means to have a career, to fulfill contracts and meet deadlines, did finish a book. Adult Drama is a respectable effort, if a little derivative—imitation Jia Tolentino crossed with imitation Sloane Crosley. It really only snaps to life when Calloway appears, which she does, first in “I Was Caroline Calloway” (retitled “Self-Centered”) and again in “Adult Drama or the Virgin Cunt Club,” the strongest piece in the collection by far. The problem could be Beach’s personality, the opposite of Calloway’s: self-deprecating, restrained, unpersuaded that she’s interesting enough to carry an essay, never mind a whole book. Calloway, on the other hand, is convinced she’s the heroine of a great drama. This belief gives even her shitposts a certain verve and flair. She might be shameless—“I’m a genius, Lili”—might be corny—why so many pictures of herself dressed like a Disney princess?—might even be nuts—“I’m not not mentally ill,” she once told me—but she’s always original, ever watchable. 

Yet it could also be argued that Calloway is a writer. A new kind of a writer. A writer who’ll never finish a book because to finish a book is to kill the story. And a book is already a dead thing since it can’t change or adapt, be revised or edited or added to or commented on—not without a cumbersome reprinting, anyway. (Books even look like little coffins.) Digital media allows for an ongoing, interactive story, and maybe that’s the future and Calloway’s it.

Or maybe she’s what her haters have always said she is: an amusing fuckup so fame-hungry that she’s willing to turn her inability to function into a brand.

Or maybe she’s all of the above.

I don’t think Calloway can admit, even to herself, that the chances of her publishing Scammer in anything like the form she originally promised are slim. Except that she did admit it. On January 27, 2021, in a now deleted post, she wrote:

How will you expect me to deliver on writing when I am historically, famously, bad at doing exactly that?… If I could travel back in time and prevent myself from crumbling under the overnight public scrutiny into an avalanche of panic attacks, I would have liked to have tweeted out exactly this to the haters calling me a criminal during January, 2019: CHAOS IS THE BRAND, YOU DUMB, SNARKY FUCKS!!!!!

As afternoon turns to evening, I catch a plane back to New York. Leave Calloway in her old-folks home in boondocks Florida with Matisse, now in a Dr. Seuss hat. If Calloway weren’t the supreme comic ingenue of her day, her ending would be tragic. Her ending would, in fact, be that of the protagonist/antagonist of Todd Field’s #MeToo thriller, Tár. That Lydia Tár, like Caroline Calloway an American self-invention and natural transgressor, is exiled from the cultural establishment is treated as a calamity. What a devastating fall from grace we’re supposed to think when, in the final scene, we see this onetime maestro of the Berlin Philharmonic conducting the score for a video game before a collection of cosplayers in an unspecified Southeast Asian country.

But Calloway is the supreme comic screwball ingenue of her day. Therefore she understands that an audience of plushies and freaks—or retirees and kitty cats—is preferable to one of simpering, self-congratulatory members of a dwindling and increasingly irrelevant intelligentsia. Her fate is a joke, but the joke isn’t only on her. It’s also on the scared and conformist culture that laughs at her because it can’t laugh at itself. 

Embrace the chaos, you dumb, snarky fucks. 

HAIR AND MAKEUP, RONNIE PETERSON. FOR DETAILS, GO TO VF.COM/CREDITS