For a certain subset of extremely online culture enthusiasts, Caroline Calloway, a former Instagram influencer and self-proclaimed scammer, is something of a North Star; both an undeniably chaotic individual and a fascinating signifier representing the crossroads between addiction, a flawless public image, downtown party girl aspirations, and “workshops” that failed to deliver on what was advertised.
Now, almost a year after Calloway’s former landlord sued her for over $40,000 in unpaid rent, a new mini documentary from Vice catches up with the 31-year-old living a quiet, relatively normal-looking life in Sarasota, Florida.
“Nothing new happens to me here,” Calloway says in the video, which was uploaded Thursday to Vice’s YouTube channel. She says she’s reading books, managing her mental health, and working on her writing. As she puts it, she started her Instagram account when she was 20, and wiped it clean when she was 29.
“For a large part of my twenties, I really used the content that I made online to help me process my emotions and my experience of the world,” Calloway says. “I took down that boundary.”
But she still seems to have trouble maintaining her boundaries: In the Vice documentary, Calloway posts on a particularly vicious Reddit page that tracks her every move, asking if the group’s members would like to speak to her. It doesn’t go well. Later, a moderator for a “Caroline Calloway enthusiasts” page expresses regret for unkind things she’d said in the past, and advises Calloway to let the whole thing go and move on.
Calloway had been garnering attention via her Instagram for years, but first gained wider recognition in 2019—at the height of collective fascination with scammers—after she cancelled a spate of 45-person, $165-per-person “creativity workshops.” This severely angered her legion of 800,000 Instagram followers and caught the attention of eagle-eyed NYC journalists, many of whom reacted to her with total scorn.
Over the years, Calloway continued to proffer, and inspire, increasingly alarming content. Her ex-best friend Natalie Beach penned a viral essay for The Cut in which she alleged that she was responsible for ghostwriting the viral Instagram captions that had landed Calloway the lucrative book deal she later backed out of. Calloway denies this, saying that it was her writing that catapulted her to viral fame as a photogenic expat student at Cambridge University.
Her name is still brought up on occasion at Brooklyn dinner parties; a person I chatted with recently seethed with rage at the very thought of Calloway. “She’s insane,” the woman spat. “She used to drug her cat and bring it to parties. She tried to push someone down the stairs!”
Whether any of that is true, I have no idea. But what’s clear is that Caroline Calloway as a concept has become something of an urban legend or a flower crown-adorned spirit, haunting the collective consciousness of status-junkie New Yorkers.
Meanwhile, as evidenced by Vice’s new doc, Caroline Calloway the person seems to be doing a whole lot better. Hopefully we’ll get to read that long-promised memoir within the next decade.
The Daily Beast