Shephard dreamed of a scene with all sorts of internet-famous scammers, but she got lucky with a big name willing to play herself.
“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. It’s pretty horrible to be a woman who the entire internet piles on and rips apart for making some mistakes. 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. “We got drunk and talked about the internet. “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. 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.