There are so many novels and films – the Ripley series, for example, and every iteration of the Ocean’s Eleven franchise – that rely on the reader / viewer absolutely loving a scam artist. I don’t love Caroline Calloway, social media’s most beloved / beleagured (and self-described) scammer, but I do find her very entertaining.
Calloway is one of those people who feels like they escaped from a novel and refuse to go back into its pages. The 31-year-old is a recent obsession for British newspapers (based on her new memoir Scammer), a medium-term obsession for US magazines (her former collaborator / ghostwriter Natalie Beach hit it big with a New York magazine tell-all in 2019), and a longstanding obsession for Instagram addicts and influencer analysers since 2013. Like an F Scott Fitzgerald character on the run, Calloway skips insouciantly across social media feeds whether you want her to or not. She is the grifter who tells you she’s grifting, who wants you to enjoy the experience.
Calloway’s screw-ups, attention-seeking stunts, interviews, scandals and emotional outbursts are her work; the books, the merchandise, the talk of a movie or prestige streaming series about her life are all incidental. At this point, you probably find yourself wondering: who cares? Well, enough people for Calloway to appear in a Telegraph page-lead and many, many feature interviews across the British press. In part, it’s because she’s a Holly Golightly who finagled her way into Cambridge university.
I didn’t think I’d get into Cambridge and was surprised and delighted when I did. But Calloway? She knew she would. The scion of a real-estate family where the fortune didn’t make it all the way down to her generation, she has always seemed to have drama swirling around her: when she got into Cambridge, she instantly became a face about town; when her father tragically took his own life, she was the one who found his body.
Calloway’s route to the university was typically twisty: already an undergraduate at New York University, she wanted to orchestrate a transatlantic trade for herself – a reinvention as an American in the Fens (“Fenland Polytechnic” is the familiar sneer thrown at Cambridge by Westminster-bound graduates of the odious Oxford). She had already executed her first reinvention before she arrived in England, transforming from “plain Jane” Caroline Gotschall into Caroline Calloway, the Gatsby girl with the knack for Instagram captions telling high-art tales of low-down-and-dirty Cambridge hedonism (even though they might actually have been penned by Beach).
Calloway slipped into Cambridge on the third go; she claims it was via a fraudulent application. She told Vanity Fair: “I lied on my application. I forged my transcript when I got in.” The trouble is… that might be a lie itself. Calloway is a gifted storyteller or “scammer” as the title of her book has it. But I don’t believe she was at Cambridge through anything other than merit. She’s whip smart and academically capable. It simply serves her narrative to now claim that the author of Scammer, the “Caroline Calloway” character, tricked her way, Loki-like, into an elite university.
Calloway built her fame by buying 40,000 followers on Instagram for less than £5 in 2013, then building a real audience by targeting fans of IP like the Harry Potter films and Twilight. She then harnessed controversy after controversy to build up an audience of 645,000 Instagram followers and a hungry attention from the “mainstream” media for stories about her and interviews with her. It’s a more literary version of the scheme that propelled the Kardashian family to fame (in that case, Kim Kardashian’s “momager” Kris Jenner parlayed her daughter’s leaked sex tape into reality-TV ubiquity).
“I love fame,” Calloway told The Guardian in 2020, “I love being written about.” So here I am, doing what she loves.
I don’t really know Caroline Calloway but I don’t not know her either. Back in 2020, I wrote an essay about the Calloway phenomenon in which I compared her to Loki and said people who hated her should “burn [their] Joan Didion books and stop venerating F Scott Fitzgerald.” Of course, she liked it.
Her skill is to make people trust her and then use that trust for financial, social, and cultural gain
She posted about it on her Instagram story and we started to talk in Insta DMs. I won’t share them – Calloway would – but they’re interesting; she’s charming, funny, and can make you part of her story with the consummate ease of… well, some would say the social climber and others, including Calloway, would say the scammer. It’s no surprise to me that interviewers from The Times and Telegraph confessed to liking her; she knows how to charm, disarm, and persuade the listener to become complicit in the story she is telling.
It’s even less of a surprise that the picture editors at the Telegraph – always enamoured of a hot blonde – made her a page lead.
Calloway has a genius for the most modern sort of fame, the Kardashian ease of self-publicity mixed with the brazenness of the best TikTok and Instagram influencers. Her skill is to make people trust her and then use that trust for financial, social, and cultural gain. When Calloway wanted to pay back an advance for a book she didn’t deliver, she set up an OnlyFans account with topless photos of her dressed as famous literary characters – it was self-consciously reaching for iconic, obviously provocative, and commercially astute. The middle-aged men who purported to despise her signed up in their droves to have the kind of hate wanks they last enjoyed during their horrible divorces.
Calloway understands an iron law of modern media and showbiz: all attention has cash value – good or bad. She told The Guardian: “I don’t really mind if people think I’m a bad writer. If they don’t understand my weird Instagram performance art or they find my long captions annoying. That’s part of the package of being in the public eye, and honestly I find it exhilarating.” Her fans trust that Calloway will be entertaining; they don’t expect her to be reliable. It’s why her many broken promises have not ended her or led to any sort of cancellation that sticks. The “scam” is so blatant it is almost comforting; people who like Calloway trust she will entertain and her obsessive “haters” trust she will keep giving them new material to work with.
Caroline Calloway is a mirror – you either see yourself or your own disgust. Your response says more about you than it does about her.
I wrote in 2020: “Caroline Calloway is not stopping.” If it’s gauche to say, “I told you so,” then call me gauche. I knew that Caroline Calloway – it always feels more correct to say her name in full – was in it for the long game. And there’s no sign she will stop now. Scammer is a fascinating book – more for its route to publication than what’s between its covers – but that doesn’t really matter; the “Caroline Calloway” character is the real product and it is selling like the hottest of hot cakes (or perhaps takes).
Calloway set up an OnlyFans account with topless photos of her dressed as famous literary characters
There’s every chance you’ve read to this point and are angry and confused. Why does this young woman, who has time and again failed to deliver on projects she promised and whose writing is solipsistic and narrow in its focus, matter? Because we have always been taken with autobiographical artists, and autobiography has always been an interaction between establishing readers’ trust and spinning entertaining lies or half-truths that can withstand the heat of our suspended disbelief.
Joan Didion was not much different from Caroline Calloway, she just gave us the pretence of froideur and aloofness. Calloway is more honest and does not hide her avarice or ego behind a front of “coolness”. As Alice Glass, then of the band Crystal Castles, said when she was asked to define “cool”, after topping the NME’s Cool List: “I have no definition of it. Ask the mummified jazz musicians from the 1950s who started using it. We need new idioms. We need to stop talking like beatniks.”
Caroline Calloway is working with new idioms and, at the same time, playing a game as old as time. She’s Anna Nicole Smith with an Instagram account and no need to marry a desiccated multi-millionaire; she’s Tom Ripley without murder on her mind. Ego is the engine for all writers: Calloway is just willing to lift the bonnet and show the noisy, greasy, dirty parts inside.
Mic Wright is a journalist based in London. He writes about technology, culture and politics
