“There is more raw material here than anywhere else in the world,” Wilson said.
Sitting in the backyard of his apartment in Ridgewood, Queens, wearing a flannel jacket and glasses with thick frames, Wilson has a soft-spoken presence. But his apparent passiveness masks a finely attenuated eye for the absurdity of life in the city. When our conversation is interrupted, at one point, by the distant sound of a neighbor’s violently phlegmatic cough, Wilson breaks into a mockingly repulsed “eww” and adds a deadpan side-eye. It was the day after President Trump announced that he had Covid-19, and Wilson explained that his morning had been spent filming newsstands across the city in search of New York Post headlines announcing the news.
Inspired by documentary filmmakers like Les Blank, Wilson practices an approach that he describes as “letting the story come to you.” For these early films, which he would upload to Vimeo with little self promotion, this process was intensive. He estimates that each of his 10-minute shorts required a year of gathering footage, in addition to writing and editing, all of this done in his free time while he worked a series of “low-rent” jobs, like editing surveillance footage for a private investigator.
Though the process has been streamlined significantly by an HBO budget, which allowed for a second shooting crew and additional writers, it took two years to shoot and edit the show’s six episodes, which clock in at around 25 minutes each.
“A lot of documentaries are about something that already happened, but I think people are kind of afraid to let the story find them,” he said. “It’s scary because you might not end up with something good.”
An example of “something good” comes in the show’s pilot, “How To Make Small Talk,” in which Wilson explores the ins and outs of polite chatter and his own difficulties with it. To reinforce a point about location, he went to a WrestleMania event in New Jersey and conducted interviews (which are unscripted throughout the show) with attendees, the first being with a self-styled “child predator hunter” shown chugging a beer while wearing a fur coat. The chance encounter led Wilson to go home with the man and film him as he attempted to entrap a predator, rerouting the direction of the episode.
“His process is definitely a Catch-22,” said Alice Gregory, one of the show’s three writers (as well as a contributing editor for The New York Times’s T Magazine). “Our scripts were really provisional documents — we would put an ideal scenario on paper but we knew it was going to change quite a lot.”