The creators of Not Okay knew exactly what they were doing when they enlisted Caroline Calloway for a cameo in their influencer dramedy. Still: Why on earth would the maligned social media presence appear in a damning portrait that feels entirely based on her life? The intrigue surrounding Calloway never disappoints.
Not Okay isn’t about Caroline Calloway, but really, it is. Quinn Shephard’s Instagram satire follows Danni (a miraculous Zoey Deutch), a washed-up journalist—when I use the word “journalist,” I mean a writer for Buzzfeed operating out of The Wing—with a penchant for fame. She’s 10 followers short of her desired count: 50 followers. Danni, who watches Caroline Calloway inspo vids on the reg, is a nobody living in the brain of a Kardashian.
So, she commits the unthinkable. Danni pretends to be a victim in a fictionalized terrorist attack at the Arc de Triomphe in Paris, which earns her a few hundred new followers. That’s not enough for her, so she befriends a high schooler (Mia Isaac) recovering from a mass shooting that took her sister’s life. Then, Danni decides to steal her words for an about trauma that goes viral, finally earning the wannabe a flurry of undeserved attention.
Caroline Calloway didn’t go that far. (That being said, the influencer seems to commit a new atrocity every month, so maybe it’s only a matter of time.) Explaining Calloway’s actions to anyone who hasn’t been following along since the 2019 Cut exposé feels like performing a one-man show of The Godfather to a bunch of seven-year-olds. It’s nonsensical. It’s chaotic. It gives me a headache.
But it’s also so fun to spread the gospel of one of our world’s best scammers, which is why I will continue to explain the situation until the end of the world. Calloway was famous in the 2014 #Wanderlust era of Instagram, where she rose to fame for aesthetic quirky girl pics and brilliant captions like, “Much like Ring Pops and disposable razors, memories deteriorate with use.”
Years later, her ex-BFF Natalie Beach penned a trailblazing essay about years in the trenches serving as Calloway’s ghostwriter. Folks took to Calloway and Beach’s story as they did any other scammer: They ruthlessly (and rightfully) made fun of Calloway for her too-wealthy-to-care attitude. Alas, the harsh words against Calloway only fueled her into more fame. The influencer used every word spoken against her as if it was a prize. She became famous for being infamous. In the past few years, Calloway has made headlines for her self-destructive interview with Ziwe, for writing a book that’s never seen the light of day (does it exist?), and for screwing over her West Village landlord.
Now, she’s making yet another headline with this article (one of many) about Not Okay. The film—which is entertaining in a way that feels somewhat gross and anti-feminist, kind of like Caroline Calloway’s entire persona—features Calloway in the beginning with fake self care YouTube videos Danni watches, a subtle way to introduce her bigger role later.
After Danni is outed as a public menace, she attends an “online shaming support group” (featuring an empty chair reserved for Kendall Jenner) led by none other than Caroline Calloway in her unmistakable sky blue tracksuit. If only the group had made flower crowns and chatted with Ziwe before the session!
Calloway is satirized in the main story, but as for her role in the actual film, the influencer is completely level-headed. She says nothing absurd at the meeting, even offering Danni some advice—it feels out of character. Seeing a completely hinged Caroline Calloway is uncanny.
Caroline and Danni share a remarkable number of similarities—unwillingness to admit they’re wrong, obsession with online popularity, cringe-inducing presences full of tongues sticking out—so putting them in one scene together feels like the film put a mirror between them. It’s a hilarious self-own from Calloway, who has been known to retweet any mention of her name (even if it’s terrible) on Twitter. The pair even look alike. They could be cousins.
Why did Caroline Calloway agree to star in a film that degrades her kind? She has admitted to loving fame, no matter the cost of cancellation. She will do anything to see her name plastered everywhere, regardless of the context. While Natalie Beach has moved onto a more private life, Calloway somehow emerged victorious from the article in The Cut—simply because she has become notorious, which is great for clout.
The fact that Not Okay can mock this behavior while also endorsing it has puzzled me: Is it a good thing we’re giving this influencer a platform yet again? Or does it only emphasize the fact that social media celebs will do anything for fame? Who knows. There’s never an answer with Caroline Calloway—something that will continue to be astounding (in the best and worst ways) for a long, long time.