‘Not Okay’: How Filmmaker Quinn Shephard Sifted Through Notorious Scammers for That Influencer Cameo

SPOILERS: Shephard tells IndieWire she dreamed of a scene cast with internet-famous scammers, but she got lucky with one big name willing to play herself.
'Not Okay': How Filmmaker Quinn Shephard Cast Caroline Calloway
"Not Okay"

[Editor’s note: The following story contains spoilers for “Not Okay.”]

That viral influencer and alleged scammer Caroline Calloway appears in Quinn Shephard’s hilarious internet satire “Not Okay” isn’t a surprise: The figuratively canceled Instagram personality (and literally canceled author) repeatedly touted her involvement in the Hulu film with tweets and retweets (of course!) for all manner of marketing materials, including the trailer that features Calloway appearing as, well, herself.

Given the subject matter of the film, it’s canny casting defined. Shephard’s sophomore outing follows wannabe influencer Danni Sanders (Zoey Deutch) as she lies her way into viral fame and must face the fallout of her own scam. Although not as well known as scammer brethren like Anna Delvey, Elizabeth Holmes, or Martin Shrekli, Calloway is infamous to a certain class of the very online who are also the kind of people who will enjoy Shephard’s (very smart) film. (Need a Calloway primer? This 2020 Guardian piece does that and more.)

When it came finding actual canceled internet stars for a key scene that sees Danni attending a scammers support group, Shephard cast a wide net.

“The idea initially was that the support group was full of people who had gotten online shamed and canceled,” Shephard told IndieWire during a recent interview. “Zoey and I made it our life’s mission to try to get as many cameos as possible in this scene. I can’t say who, but Zoey and I have FaceTimed with so many ‘canceled’ people who almost did this movie. It is insane the people whose numbers I have in my phone. We did so many calls. Somebody would love it, but then their rep would be like, ‘Absolutely not.’ Or we would write jokes for them: ‘What do you think of these?’ and they’d be like, ‘Ooh, I don’t know about that.'”

Shephard said Calloway was always top of mind. “It was always an idea to have Caroline in it, because right when I was writing the story, it was about to be the summer of scam,” Shephard said. “She also represents everything Danni wants to be, in that she is a writer but she’s also an influencer. That’s Danni’s mental mashup.”

While some balked at Shephard’s ideas, the filmmaker said that was never the case with Calloway. (IndieWire reached out to Calloway on Instagram, appropriately enough, but did not receive a response.)

“She does get it, that’s what was so funny,” she said. “Caroline just immediately got it and was like, ‘I like making fun of myself. I understand that this movie is also not a takedown of people like me.’ Let me rephrase that: It is and it isn’t. It’s a criticism of people, but it’s basically being like, I don’t think destroying their lives is necessarily the answer. The answer is that Danni needs to do self-reflection.”

Shephard soon met with Calloway for a revealing evening in which they discussed Calloway’s experience, how it’s reflected in Shephard’s film, and the general ickiness of internet culture. Calloway had the role (of herself) even before the conversation began, but her insights appealed to Shephard.

“We went to a very fun dinner and drinks after, which was maybe the most hungover I’ve ever been in my entire life,” she said. “We got drunk and talked about the internet. It was intense hearing from her side what she went through. It’s pretty horrible to be a woman who the entire internet piles on and rips apart for making some mistakes. The way that people love to watch women suffer is part of this story.”

“We’re not saying Danni, again, doesn’t deserve consequences,” Shephard added. “She does deserve consequences, but is destroying woman’s life, doxxing her, sending her rape threats the answer? Also no.”

“Not Okay” is now streaming on Hulu.

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