Caroline Calloway Is (Basically) Done Being a Scammer
Updated March 11, 2024, at 3:55 p.m.
The last time Caroline Calloway was in the Square, she went to the Harvard Art Museums on a date with a charming Australian art history student, to a party at the Lampoon where Scarlett Johansson had lit a cigarette on the fireplace the week before, and to Adams House to grieve her father, class of 1975, on the crimson couches in the library, while blue dawn broke over Cambridge and the Lampoon coke wore off.
There was a time when Caroline Calloway was (sort of) famous (to some people) — a time when the sight of her lounging on a couch in Adams House in 2019 would have been the stuff of at least a few Instagram stories. In the early years of the social media site, Calloway made a name and following for herself posting long captions romanticizing her lavish lifestyle and high-brow adventures with her old money European peers at Cambridge University. Think castles and flower crowns and Renaissance paintings and dating a cute Swedish polo player and bottles of wine on the banks of the River Cam. Calloway became Instagram-famous in the early 2010s, when it was both very cool and very rare to do so.
By the time she had amassed 300,000 followers — an incredible feat in the dark ages of 2015 Instagram — she leveraged those captions into a $375,000 book deal. With the sale of the international rights to the book, this figure came to the tune of half a million dollars. Only she never wrote this book, and never intended to.
By 2017, her book deal fell through, and she was more than $100,000 in debt. And battling a pill addiction. She sold $165 tickets to a trainwreck “Creativity Workshop” that was compared to Fyre Fest. In 2019, her ex-best-friend Natalie Beach published an article in The Cut alleging that she was Calloway’s ghostwriter. It was The Cut’s most read article of 2019. A week later, Calloway’s father died by suicide. She gave the eulogy at her father’s funeral the morning after she appeared at a live show of the podcast Red Scare.
“The trip to Harvard just helped me so much. I needed to find some sort of pressure release from all that pain that was going on, so that I could think straight and make the right business decisions and put one foot in front of the other,” she says, before quickly pivoting to me. “Yeah, so you never answered my question. Do you want to be a writer?”
Calloway, as I assumed and as she admits unprompted, only agreed to do this interview because I go to Harvard. The coin of her realm is attention — but a certain kind of attention, from a certain name-dropping, media-literate, meta-analytical crowd. She has appeared in the New York Times, Vanity Fair, New York Magazine, British Vogue, and the New Yorker. Attempts have been made to untangle her in countless Substack thinkpieces.
Enter The Harvard Crimson. This interview is special because it is a rare situation in which Calloway’s interviewer is beneath her. Journalists who profile her tend to emphasize the way in which Calloway tries to charm them, befriend them, and use their connections. But I am a child. I have nothing to offer Calloway other than my association with Harvard and a perhaps generous eye.
She seems to crave it. She asks me questions about my life, tells me she can see me raising chickens one day, and says that I should never let a man make me feel bad about loving “Real Housewives.” She texts me TikToks about Joe Alwyn and Lorde. She references the drama with the girl who claims Olivia Rodrigo stole her idea for her SNL performance, and I tell her I haven’t heard about it, and she tells me “Sarah, I’m worried for you. This cannot be our intergenerational dynamic.”
I know this is just what she does, and that she wants to create a warmth and intimacy between us so I think she’s cool.
Well, it worked, and I love her. If you’re coming — in George Santos’s America — to read a rejection of content consumption, you will not find it here. I will not indict Caroline Calloway simply for wanting to be liked and talked about. Sorry, r/SmolBeanSnark!
After the era during which Calloway passed through Harvard, she lived a series of grifts on her scammer reputation in New York. She sold $210 Snake Oil, which consisted of 70 percent grapeseed oil and 30 percent other oils like ylang-ylang, frankincense, and pomegranate. Her Instagram stories showed her on the floor of her famously anxiety-inducing apartment mixing vials by hand. She sold her life rights to Lena Dunham. (The deal has since expired as Dunham has moved on to direct a movie about Polly Pocket.) She went clubbing with her cat, Matisse, and dropped acid with the journalist writing about it.
She joined OnlyFans and made $25,000 a month selling topless photos of herself dressed as literary heroines for an audience she imagines as “boys who went to Princeton and now work on Wall Street and who think I would have been mean to them in middle school because they don’t know I was being bullied for my crutches then.”
She threw chaotic parties at her West Village apartment, on which she didn’t pay the rent for the last year. Her landlord sued her for the $40,000 of said rent and for the disheveled state in which she left the apartment. And in 2022, she left it all behind to move to Sarasota, Florida and immerse herself in her writing.
“How old are you?” she asks me. Calloway is 32 — born in Fairfax Virginia at 6:30 a.m. on Dec. 5, 1991, making her a quintuple Sagittarius. I tell her I’m 21.
“When I was 21, I was nothing worth writing about. Or nothing worth writing a whole book — a whole best-selling book about,” she flexes, faux-facetiously.
“I was so hungry for it. And I definitely put myself in situations that would help ameliorate that. From 2010 to 2017, I was doing it for the plot nonstop,” she says. “If nothing interesting ever happened to me again, and if I never met a new person for the rest of my life, I would still have enough memories, enough professional connections, and now accumulated fame, enough of a lot of different things that I didn’t have at 21, that I do now, that I just don’t live like that anymore.”
Sarasota Caroline seems a sharp departure from West Village Caroline. She has a “chic lofted office downtown” that she goes to six days a week — four for writing, two for shipping and other hot girl shit. She made a rule for herself: no passport until you finish your first book. Then, you can go anywhere in the world except your favorite place: New York. Sarasota Caroline is so stable that she won’t even go back to New York until she can buy an apartment in the West Village. Emphasis on “buy,” not “rent”; emphasis on “West Village,” not anywhere else.
Because she spent a decade living her life in such a way that she could write about it in the future, she’s ready for her next chapter.
“The driving force of my very existence is,” she reveals to me, “I have the memories. I have the friends. It’s time to put them on the page.”
Last June, the aforementioned Natalie Beach came out with a book of essays, “Adult Drama.” But before that — Calloway can’t remember when, just that it was before Beach’s book came out — Calloway released her long-awaited book, “Scammer,” which she started accepting preorders for three years before its publication.
Within six months, “Scammer” made $300,000, per Calloway. In an Instagram caption on a post featuring a New Yorker article about both books, she writes:
“GOD, MAKE ME THE BIGGER PERSON — JUST NOT YET!!!!!! GIVE ME THIS ONE LAST DAY OF SPITEFUL GLEE AND GLOATING, AND I SWEAR TO YOU, I WILL WAKE UP TOMORROW AND NEVER MAKE ANOTHER MENTION OF AN ARTICLE THAT RAVED ABOUT MY BOOK WHILE TRASHING NATALIE’S.”
Calloway’s use of “rave” and “trash” here are perhaps a tad flattening of the article, which pointed to strengths and weaknesses in both books and noted that each author is “trapped in an endless collaboration” with the other. But generally, “Scammer” was met with surprised delight from reviewers. Vogue called it “well paced, peppered with dramatic revelation.” Stylist called it “genuinely gorgeous.” The Washington Post called it a “masterpiece.” (n.b: specifically, they said “Caroline Calloway is a lunatic who has already written a masterpiece.”)
“Scammer” is self-published by Calloway’s imprint Dead Dad Press, meaning you can only get your hands on a copy through her website. My roommate had ordered ‘Scammer (For Peasants)’ for $30, which is hand-signed and numbered — but which lacks the ribbon, decorative stickers, Ex Libris bookplate, and Italian paper inner covers of ‘Scammer (Luxury First Edition!)’ for $65. She bought it in October; it came in January.
Before I talked to Calloway, I read “Scammer” cover to cover, including the histories of the fonts she used and the 14 pages of acknowledgements. I scoffed and cackled and gasped audibly to no one in particular at certain lines, certain adjectives. She drops a lot of well-crafted analogies and a lot of names. Her descriptions of Beach are harrowing — in one anecdote, Calloway graphically describes being turned on by Beach’s description of being sexually assaulted. In another, Calloway sets out to have sex with a woman, but instead has sex with a pot-bellied man who she says looks just like Beach, down to the B-cup breasts.
“Scammer” is very unlike other books, in that Calloway keeps the “ever-living fuck”s and “like”s that are usually lost in transit between thoughts and page. I ask her what the editing process was like for “Scammer,” and she describes the three editors she worked with and the elite institutions they have degrees from.
“It’s not lost on me that all three of them are incredibly sexy men who fuck women,” she explains. “And I’ve never fucked any of them — would never fuck any of them.” This, she says, is key to the success of their working relationship. After what happened with Beach, she can’t see herself having an intimate creative relationship with a female editor any time soon. (Eventually she does answer my question about the editing process: she synthesized individual feedback from each of the three editors, but mostly stuck to her taste.)
“Scammer” is just one of three books Calloway calls her “juvenalia.” “The Cambridge Captions” and “I Am Caroline Calloway,” which will complete the trilogy, are both available for preorder for $65 each, though they haven’t been released yet.
The former is a compilation of Calloway’s Instagram captions from her days at Cambridge, the ones that Beach took partial credit for in The Cut — a Swiftian re-record, if you will, to own the copy that Calloway maintains she alone wrote. “If you’re so sure you wrote them, sue me,” she says to a hypothetical Beach. “Show me any proof that you fucking wrote this. This is mine.”
When Calloway tells me this, I believe her because, as I mentioned, she has bewitched me. It was not always this way: when the Cut article came out my junior year of high school, I was 100 percent team Beach. In the piece, Beach alleges she was Calloway’s ghostwriter for her Instagram captions during the summer of 2013, as well as for the book proposal that never came to fruition. Beach describes an incredibly toxic and exploitative relationship in which Calloway made her feel small and used.
In “I Am Caroline Calloway,” the third work in her “juvenalia,” Calloway says she will explain her side of the story. After its publication, Calloway explains, she won’t have to answer any more questions about Beach — she can just direct hypothetical journalists to the text. While she says she’s over being defined in relation to Beach, she also knows that everything that went down is an important part of her narrative arc. And her brand.
“I really believe that one of the reasons Natalie’s book sold so few copies and that she got so little press for her book, was that the angle that her imprint tried to use was like: ‘With ‘Adult Drama,’ Natalie Beach leaves the drama behind,’ or, like, ‘Natalie is breaking away from her story with Caroline,’’’ she says. “And ultimately, that’s absolutely what I want to do, too. But you can never tell the public when they’re done with a story,” Calloway expounds. A smart public figure, she explains to me, must “overfeed the public with that story until the public says, ‘Enough, we don’t want to hear about it.’”
In an email in response, Beach asks who “would want to spend their whole career retelling the story of one band coworker?”
“Sounds like hell,” she adds. “I remain excited about the work I’ve been doing, and relieved to have closed the book on writing and thinking about my time with Caroline. To state the obvious, there are more urgent matters at hand than litigating 10-year-old Instagram captions.”
When I hop onto our second Zoom, Calloway is making pottery. I’m well-versed enough to know that she is making pottery so that when I write about our conversation, I’ll say “Calloway is making pottery.” But, alas, she is!
With Calloway, it’s hard to separate the artist from the art, because the art is the artist herself, and the artist is her work, and it’s all performance, and truth — which is the art, and the artist, and the performance — is besides the point. How do you write faithfully about someone whose life is theater in the round? To what extent do I trust what she’s doing, and the feelings she engenders?
In the Callowayan spirit of pop academia, I turn here to Susan Sontag. In her 1964 essay “Notes on Camp,” Sontag writes: “Camp sees everything in quotation marks. It’s not a lamp, but a ‘lamp’; not a woman but a ‘woman.’ To perceive Camp in objects and persons is to understand Being-as-Playing-a-Role. It is the farthest extension, in sensibility, of the metaphor of life as theater.”
To be clear: I don’t think Calloway is Camp. I don’t know if Calloway thinks she’s Camp. Probably she does. I do think, though, that Calloway lives her life between quotation marks, and that the role she plays has slowly become her real self. Calloway is a ‘scammer,’ at least in narrative, but she’s no Elizabeth Holmes or Anna Delvey. What she’s stealing isn’t money or any other exhaustible resource — it’s attention. And are you not entertained?
As always, Calloway has projects on the horizon: she’s releasing a “scamazine,” and turquoise velour sweatpants with “SCAMMER” in rhinestones across the butt. She used $20,000 of her OnlyFans money to buy up rare, out-of-print books about an academic subject she’s passionate about that she intends to edit into an anthology. But she can’t tell you what that subject is. It’s a surprise.
I ask Calloway if she thinks the scammer branding will get stale, especially now that she’s following through on her projects.
“It’s been terrible for my reputation. I mean, people finally know that I’m not a scammer now. Like, how am I supposed to keep up my reputation when people are out here slandering my name? Calling my book a ‘masterpiece?’” she once again flexes faux-facetiously. But she plans for those projects to be the last with the scammer branding; she’ll still occasionally turn to it, in the way that Cambridge used to be her brand, but now, it is just one of many moving parts of what she calls the “Caroline Calloway cinematic universe.”
In the meantime, Calloway considers herself at the forefront of a movement in the publishing world, creating a path for authors to sell books to their fans in the digital age. No one out there is really doing the Caroline Calloway Thing.
Calloway changed her name from Caroline Calloway Gotschall to Caroline Gotschall Calloway because “Caroline Calloway” would look better on the cover of a book. She bought 40,000 Instagram followers to grow her reach. She forged her transcript to transfer to Cambridge from New York University because, she says, couldn’t stand to live the rest of her life with an NYU email address. She’s always planned on being a memoirist, and she has molded the digital landscape to be both her diary and its fodder.
“I was only able to take Instagram as seriously as I did a decade ago because I’ve just always felt in my heart of hearts that a sentence tapped by thumbs into a screen is inherently as valuable as the same sentence printed inside the covers of a book,” she explains. Such is the guiding ethos of Caroline Calloway’s whole deal: the democratization of memoir, the reclamation of girlbossing.
“I actually think ultimately, in the long run, my first priority in this life is my art,” Calloway says. “If it’s: make books that live on after your death, or have a fulfilling family and be happy, I’m choosing books 10 times out of 10. I would rather make my art than be happy.”
— Magazine writer Sarah W. Faber can be reached at sarah.faber@thecrimson.com.