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How to Make a Second Season

HBO’s ‘How to With John Wilson’ was an unexpected crowd-pleaser in 2020. As it turns out, things only got more interesting after taking everyone by surprise.

HBO/Ringer illustration

When gathering material for his show, John Wilson tries to avoid high expectations. That way, “if I witness something incredible, it’s just a perk that I wouldn’t have had otherwise.”

Take, for example, a recent interview with a funeral director who was selling a classic-car-shaped casket. Initially, the conversation wasn’t terribly interesting. Then the man asked a question: “Do you want to see the other room?”

From there, Wilson was given a tour of his subject’s collection of ancient Egypt–themed artifacts. Then he was led to another, more hidden, room. This one held a wall-to-wall taxidermy display that would’ve made Mr. Burns envious. There were rows of mounted deer, wolves, bison, bears, birds, and even a mountain lion. The funeral director, it turned out, moonlighted as a terrifyingly prolific hunter. “My business is tough,” he says into Wilson’s camera. “You’re around people all the time. It’s just my way of escaping, getting away from everything.”

The reveal, which appears in the second season of HBO’s How to With John Wilson, helps tie up an episode that begins with the host’s quest to secure street parking in New York. How things go from there to a stuffed five-point buck is the essence of the journey, but the turn took Wilson completely by surprise. “I was just speechless,” he says. “Moments like that are like a religious experience for me. Or maybe the closest thing to it.”

“After you shoot it, you don’t feel that great, but I mean, it’s nice,” the man tells Wilson while looking at all of his kills. “It’s like anything. You got it—now what do you do?”

Over the past year, Wilson has wondered the same thing. The first season of his docuseries, a painstakingly curated collection of extraordinary vignettes of city life, was like a perfect debut album. The idea of making a follow-up that lived up to the original intimidated him. But then he realized that he was more prepared to do it than he’d thought.

“I was worried that we wouldn’t be able to capture as much lightning in a bottle because so much of it comes down to pure chance,” the 35-year-old Wilson says. “But it just wasn’t the case. I feel like the experiment continues to work in a weird way. The more you try and the more boots you have on the ground, the better your chance is of capturing some once-in-a-lifetime stuff.”

Though the first season of How to ... felt like a complete story, Wilson now views it as only the beginning, his way of bringing the audience into his world. And now, given the chance to pick up where he left off, he’s decided to pull them in even deeper. “I wanted people to get familiar with me, maybe see if they were interested in anything I had to say or my story,” Wilson says. “It’s like when you meet a new friend. You tell them little by little, and you eventually get to the really mortifying stuff.”

If Wilson has a superpower, it’s his ability to humanely depict vulnerability—especially his own. Whether it’s catching actor Kyle MacLachlan futilely swiping his MetroCard in the subway, filming an anti-circumcision advocate eagerly testing a foreskin restoration device, or documenting his relationship with his elderly landlord, he captures his subjects in a way that’s far warmer than it is exploitative. Wilson stuffed the second season of his show with dozens of these kinds of moments, including surreal experiences from his own life. There’s one incident, involving a run-in he had in college with people who went on to shepherd a prominent cult you’ve probably heard of, that needs to be seen to be believed.

“At this point, [it’s] in the zeitgeist,” Wilson says, “and maybe we can get some people interested in this extremely weird, embarrassing, incriminating story of mine.”

For its creator, producing the series is like putting together a puzzle before knowing what the final picture is supposed to look like. “That’s what makes it so fun,” Wilson says. But the process is complex. He and his team shoot hundreds of hours of video, editors log and sort it, and then he begins to piece it all together. “I get everything,” he says. On his computer, Wilson has the show’s master sequence and side streams from which he can pluck relevant clips. “They’re more themed based on the emotion I’m trying to draw out,” he adds.

How to … isn’t built like a linear TV show, but Wilson still maps out episodes before shooting begins. “I tried to have the scripts as tight as I can make them,” he says, “even though they all get blown apart almost instantly.”

This season, journalist and bestselling author Susan Orlean and absurdist comedian Conner O’Malley joined Wilson, Michael Koman, and Alice Gregory in the writers’ room. Both brought their own sensibilities to the show. It was Orlean who came up with an idea that inspired a scene from the upcoming episode “How to Throw Out Your Batteries.” She mentioned a divorced friend of hers who wasn’t sure what to do with her wedding ring. Around that time, Wilson happened to be scouring Craigslist and noticed that someone was selling old batteries. That piqued his interest enough to request an interview. This person, it turned out, had more to show Wilson than just a bunch of antique Rayovacs. Like Orlean’s friend, the seller had split with an ex and was reluctant to part with her wedding rings. “That is to me an out-of-body experience,” Wilson says. “When you’ve roughly conceived of something and it’s just delivered to you in a much more interesting way than you ever could have conceived.”

O’Malley’s influence on Season 2 is slightly less literary than Orlean’s, but no less important. Like Wilson, he has experience making videos that often feature hypnotic man-on-the-street interviews. “I’ve always been a big fan of Conner’s ever since his Vine days when he was also a mysterious figure behind the camera,” Wilson says.

Their first meeting, however, didn’t go well. “I really pissed him off,” Wilson says. “I had a hand buzzer with me, during a very annoying phase of my life. I hand-buzzed his friend, and his friend got really upset. This was years ago. Conner didn’t want to talk to me.” But they eventually reconciled, he adds, and “I ended up approaching him to write on the show. He was super into it.”

It was O’Malley who suggested that Wilson track down one of the anti-gourmands who film themselves eating expired, decades-old, military-issued Meals, Ready-to-Eat. “That was something that Conner was obsessed with,” he says. “This very specific niche community on YouTube.” If there’s something that separates Wilson from other experiential filmmakers, it’s his low-key, never-overeager curiosity. “I think it comes down to just asking questions and not trying to lead it in one way or another,” he says. “I know it sounds simple. Lean into the dead air and let them fill space.”

Never one to turn down a new experience, Wilson sampled one of his interview subject’s MREs. At the time, he retched. Thinking back on it now, though, he doesn’t remember it being that bad. “It tasted,” he says, “kind of like normal airport food.”

Wilson loves searching eBay for vintage T-shirts. During a recent chat, he even got up from his chair to grab one of his favorites. “This is a classic,” he said, holding up an old tee emblazoned with this: “If Assholes Could Fly This Place Would Be An Airport.”

The item, something a Jersey Shore souvenir shop probably sold in the ’80s, is pure kitsch. The fact that Wilson came upon—and got a kick out of—it isn’t surprising. After all, he has an uncanny ability to pull something interesting out of a sea of mundanity. But he’ll tell you that there’s no magic to it. “I’m just trying to get to the core of who I am and who we all are,” Wilson says.

His only trick is that he’s always looking for something. He just rarely knows what. And that approach leads to unexpected discoveries. In Season 2 of How to With John Wilson, there are too many surprising images to count. But there are a few in it that’ll stick with you for a long time: a shot of a cat with a still-flapping bird in its mouth; sneaked footage of the filming of a prestige TV show; a live look at a guy in a car sucking on a woman’s toes.

“A lot of the time,” Wilson says, “the best stuff is stuff that you would have never anticipated.”

That philosophy doesn’t just apply to Wilson’s subjects. “Everything is fair game throughout my entire life,” he says. He hopes that the audience is ready to learn more about his past, no matter how strange it might be to them. “With Season 2,” he says, “it seemed like people had invested in this story and I felt comfortable throwing all this other stuff into it that I thought may have been a bit too intense during the first season. Because you’re still getting to know the character.”

Then he quickly corrected himself, adjusting his lens to find a shred more truth: “Or, me.”

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