Come for the chaos, stay for the charity: the art of spinning personal scandal into media gold

“Since I was little, I wanted to be a famous memoirist, not a famous author,” Caroline Calloway tells me, cradling one of her new kittens as we speak over Facetime. “I wanted to write about my life, and I wanted to be watched.”

And watched she is: with some 700,000 Instagram followers, Calloway is no stranger to carving out a niche. Though she first garnered notice for her adventures as an Ivy League It-Girl, the trajectory of her public persona has undergone many renovations over the years—and in an unlikely twist, she has recently emerged as something of an online folk hero-cum-philanthropist, having leveraged the media’s interest in her personal scandal to raise upwards of $45,000 for COVID-19 relief funds. Her long-response essay to The Cut’s viral exposé is now being released in weekly installments online, accessible for the price of a $10+ charity donation. And not a moment too soon: as America stutters to a halt, the attention economy is booming—and with more people than ever seeking in-home entertainment, there’s never been a better time to distract yourself with what Calloway calls “the sapphic plight of two white girls you’ll never meet.”

Calloway entered the spotlight in 2015, when she began chronicling her life at Cambridge University with the detailed diaristic captions that would become a hallmark of her personal brand. At a time when Instagram was just going mainstream, she used the platform to craft a modern fairytale replete with elite cultural symbolism: think gothic architecture, handsome polo players, and romantic afternoons spent lounging on manicured lawns with twenty-something aristocrats. But while this aspirational imagery may have proved popular in the early days of social media, it’s just one aspect of the chaotic personal mythology that keeps today’s audiences rapt.

“I wanted to write about my life, and I wanted to be watched.”

Calloway’s path to fame has never been smooth. Her first brush with controversy came on the heels of success, with the mysterious dissolution of a six-figure book deal for a memoir she no longer felt able to write. She made headlines again in January of 2019, this time for poorly-organized Creativity Workshops that, at the price of $165 per ticket, were quickly billed as a one-woman Fyre Festival. Then, just when the news cycle seemed to have moved on, The Cut published a now-infamous tell-all by Calloway’s ghostwriter and former best friend Natalie Beach. In a 6,000 word essay titled “I Was Caroline Calloway,” Beach details how she played literary sidekick to the more charismatic, marketable, and self-involved Calloway, painting her ex-friend as a manipulative charleton whose unprecedented success was the result of luck, privilege, and an uncanny ability to bend the world to her whim. It quickly went viral as the publication’s most-read story of the year, and their public rift is now alleged to be the subject of two movie deals.

“People who say this is a story of two white girls vying for authorship over a handful of Instagram captions that read like bad fanfiction of fanfiction are missing the point,” Calloway writes one in one response essay installment. Instead, she likens their story to The Social Network: a contemporary creation myth about two ambitious people who team up to build a media empire, but whose differing relationship to loyalty, jealousy, class, and power leads to personal and professional complications.


It’s the first of several bold moves for Calloway this month, who appears to have shed her old persona in favor of something more chaotic and, dare I say, Online. Her recent return to Twitter has marked a new chapter for the Caroline Calloway brand: one that veers towards self-parody, thirst-traps, and what can only be described as ‘chaotic good.’ Shortly after publishing the first essay installment, Calloway leaked her own nude on Twitter and made it her pinned Tweet as a cheeky “apology” for getting the word count wrong. On April 13, she announced the launch of her OnlyFans, an NSFW social media service where subscribers pay a monthly fee to access content from their favorite creators. This transition from earnest Instagram influencer to thirsty court jester has been hailed as a genius business strategy or the public unraveling of her mental health, depending who you talk to—but there’s no denying she knows how to keep her audience hooked.

Following in the footsteps of Kim Kardashian, Calloway has managed to turn a potentially reputation-ruining event into a branding opportunity and a source of continuous revenue (when we spoke, Calloway was on track to receive upwards of $80,000 a year from OnlyFans subscriptions). Kardashian and Calloway are both natural performers who have bent the rules of the attention economy, using their keen business sensibility, an irreverence for social norms, and an innate comfort with marketing themselves to create brands that are inseparable from their work. Much as the Kardashians are “famous for being famous,” charting the course of Calloway’s career requires us to trace her intersection with a variety of cultural phenomena to the point where the apparent unexplainability of her success became a meme in and of itself. The apparent inscrutability of this kind of fame invites bemusement, jealousy, and some variation of the following question: are we witnessing the unprecedented success of a talentless narcissist, or the work of a genius business mogul with a galaxy-brain understanding of our media landscape?

Kardashian and Calloway are both natural performers who have bent the rules of the attention economy, using their keen business sensibility, an irreverence for social norms, and an innate comfort with marketing themselves to create brands that are inseparable from their work.

In recent years, the desire for aspirational narratives has been replaced by a new appetite for authenticity, intimacy, and vulnerability—and from her personal account of Adderall addiction and mental illness to her chaotic power moves, Calloway has become a perfectly flawed protagonist, whether by accident or intelligent design. 2015, an idealized lifestyle was #goals; by 2017, we were craving the messy truth behind that perfect facade; and today, we gravitate toward engrossing public feuds, soap opera-style dramas, and the cult-of-personality figures running the show. From Tiger King-cum-country musician Joe Exotic to internet personality-cum-writer-cum-artist Calloway, there’s something compelling about individuals who brazenly admit to wanting money, fame, and attention. Their larger-than-life personas—and the accompanying scandals—make them the perfect distraction in the quarantine age.

Calloway has been accused of being a performance artist, scammer, and narcissist. Her work is easily dismissed by formalists and snobs, in part because it’s impossible to cleave a clean line between the infamy of her public persona and the intimate confessional qualities that make her writing so successful. Nevertheless, Calloway understands better than her contemporaries what today’s audiences want, and has used all the tools in her arsenal to deliver a bundle of contradictions that we can spend days unraveling. From her foray into the art world to those Yale plates, there’s something for everyone—and Calloway’s expansive personal lore fosters an intense parasocial relationship with fans and haters alike.

I find myself tempted to attribute Calloway’s persona to a combination of conscious posturing and business strategy, perhaps because I myself am allergic to being earnest online. But for her, inhabiting this space feels not only natural but authentic. “A lot of online creators approach their posts as a self-contained narrative arc, whereas I think of Instagram as a 24/7 reality TV show of my life that people can tune into at any time,” she explains. “My job is not for everyone. But in the way that some people value privacy, I value performativity. I believe people when they say they feel better when stuff is private—but I hope that people can believe me when I say I feel better when stuff is public.”