The Cult of Caroline Calloway Can’t Stop Taking the Bait

I knew the day Insta-scammer Caroline Calloway would make her splashy return to the discourse would soon be upon us. I knew it the second she announced her exile to Florida. I knew it again when Calloway resurfaced from her year-long social media drought and aforementioned exile to inform us that her long-rumored book Scammer was set to publish in mid-May. And again, a month later, when she resurfaced to inform us that Scammer was now set to publish Friday, June 16—notably not mid-May. At long last, the day has come: Not only is Caroline Calloway back to plugging your social feeds with inflammatory hairballs but she’s been profiled in earnest by Vanity Fair.

Lest you’ve had the wherewithal to opt out of Scammer updates, let me briefly try to explain the satanic shroom trip that is Calloway’s life thus far. The aspiring debutante and provocateur lied to get into NYU, befriended a writer named Natalie Beach, started an Instagram account to enchant followers with the banal details of her life, dropped out of NYU and applied three times before finally getting accepted to Cambridge, was then canceled by Beach in now infamous fashion for not writing the Instagram captions (or book proposal) that made her internet famous and has suffered a litany of miniature cancellations since then. Her accolades include being racist, being antisemitic, scamming customers out of books, scamming customers out of Goop-inspired workshops, and selling non-FDA-approved bottles of Snake Oil.

Now, in what is sure to be an impending trend of profiles tracking the whereabouts of canceled personas in recovery, Calloway has gotten the slice of the traditional media landscape she’s always pined for: An honest-to-god write-up and editorial spread in a glitzy publication for the intellectual elite. It’s catnip for those well-versed in the drug-addled, coquette lore of Calloway; it’s bait for those waiting to cancel her again, or those setting out to prove they can’t be charmed by her; and it’s brain rot for people like me, who have spent far too much time trying to make sense of this woman’s Gabapentin-dollhouse brand of scandals.

The revelations in the piece range from eye-rolling—a mid-interview, perhaps accidental, perhaps planned nip slip—to disturbing (fantasizing sexual assault). Because she’s apparently so good with her words, I’m going to let Calloway dig her own grave from here.

On the money she still owes her West Village landlord: “At a certain point, I realized I could either live luxuriously or pay my rent.”

On embracing cancel culture??? “

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.”

On “surviving” cancellation???

“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.”

On Natalie Beach: “Natalie stole my identity with that piece…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.” (Beach refuted those claims, though she did cop to unintentionally getting Calloway hooked on Adderall.)

On scandals and how many one should have, ideally:

“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.”

On quitting Adderall: “I don’t take uppers anymore. 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.”

On condoms: “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.”

Most of Calloway’s incendiary fodder is designed to infuriate á la misinformation apologists of the Dimes Square scene and the Red Scare podcast (both of which are name-checked in the piece). But once you understand the intention behind Caroline’s antics—to aggravate, to goad, to rile up—the comedy routine loses all its oomph, if it ever had any oomph to begin with. That’s fine if we’re going to characterize this long-running and, at some points, dangerous con as performance art or a deranged bit by someone who is admittedly mentally ill. What we don’t need to do is glamorize it: to dress it all up in violet taffeta and designer threads and hand over a microphone.

Only time will tell: Calloway might finally put out her “manic pixie dream book.” But that doesn’t mean you have to financially support this manic pixie nightmare.