Not too long ago, John Wilson found himself on a Zoom call with Steven Soderbergh—a hero of his and a fan of his quirky HBO series, How To With John Wilson. Soderbergh had agreed to give notes on an upcoming episode of the show—one that called for some audience misdirection and, spoiler alert, concluded with what appeared to be Wilson’s car exploding in a parking lot next to a hotel. Extremely Soderbergh-y, in other words.
So Soderbergh popped up on a Zoom screen, and Wilson quickly clocked his hat.
“I was like, ‘Oh, nice Cheesecake Factory hat,’ ” recalls Wilson. “ ‘I’ve never been there. Why are you wearing that?’ ”
The question can be read as emblematic of what John Wilson is pretty good at: hunting for the revelatory in the mundane. It prompted Soderbergh to launch into an epic 10-minute homily, totally off the dome, about his love for the Cheesecake Factory, praising its massive scale, its unimpeachable consistency, its operational prowess. “It’s just a well-oiled machine,” Wilson remembers Soderbergh saying. That appreciation for professional mastery made sense to Wilson. “I can see that in his work, in a way,” he says. “He likes seeing a lot of people doing their jobs well.”
That might explain Soderbergh’s affection for How To—a sui generis job that Wilson got very, very good at. By the time it concluded its quick three-season run this summer, the show had transformed Wilson into our foremost chronicler of the strange, a feat he achieved while armed with little more than a video camera and an inquisitive spirit (and sometimes aided by a producer or two).
It’s a small miracle How To was ever on TV at all. The premise, for the uninitiated, can be hard to explain. Each nearly 30-minute episode is a kind of video essay that begins with a straightforward instructional premise—say, “How to Cover Your Furniture”—that Wilson attempts to unpack while wandering the grimy streets of New York City. Where he inevitably winds up is anyone’s guess: The aforementioned furniture episode begins with Wilson’s cat tearing up his couch and concludes with Wilson interviewing an anti-circumcision activist named Ron, who lays pants-less in bed as the skin on his penis is stretched by an elaborate foreskin-restoration device. “I have one [of the gadgets] at home,” Wilson tells me, “but I don’t know if it’s the right size. He said he had to measure me when I was erect, and I just couldn’t do that when the crew was around.”
It’s a warm fall afternoon when Wilson and I meet up in Ridgewood, Queens, where he lives. In person, he is taller than you’d expect, but he has a habit of scrunching into himself, as if to make himself more inconspicuous. We settle down at a table outside of a local bar that he frequents and he’s dressed in a monochrome-ish Brooklyn guy uniform: white T-shirt, white denim cutoffs, white Hokas. On his head is a faded cap that says PRESS in big white letters. After a few High Lifes, he’ll occasionally sneak a pull from a disposable pod vape that looks like a creamsicle. His voice isn’t quite as Kermit the Frog-y as it seems on the show, but he possesses the same sort of contagious wonderment that gives him a disarming reality distortion field. That is to say: He’s really, really good at getting his subjects to say crazy shit. One particularly memorable example is the Florida gym owner (in an episode titled “How to Work Out”) who, after a long conversation, casually dropped that he was “proud” to have unknowingly trained one of the 9/11 hijackers. “The energy was weird,” says Wilson of his meeting with the man. “That was one of the strangest interviews I've ever done.”
Sitting with him there on the sidewalk felt like observing a creature, as the writer Susan Orlean once put it, in its “most natural and self-selected setting.” Wilson’s eyes are frequently scanning the landscape for oddities, interesting juxtapositions, or other blips in the fabric of reality. Perhaps not surprisingly, elements of his series populate his real life. At one point, the Neon Sign Guy from the show walks by with his dog and stops to chat with us. Not long after that, the Hoarder Lady shuffles by before pausing to leaf through a pile of trash halfway up the block. A small part of me felt like I was being Truman Show-ed. “There’s some great Ridgewood characters,” Wilson says, as a portly orange gentleman in a lime green tank top waddles past. “Really nice fits.” That Wilson is drawn to the grist of city life and feels at home here makes all kinds of sense. When it arrived, How To was hailed for being equal parts gonzo journalism and dreamy art project, guided by his eye for the bizarre and his unflinching willingness to follow his curiosities.
The show did that rare thing where it could toggle between the grotesque and life-affirming in an instant; its inventiveness and erudition made it a darling of the creative class. The New York Times Magazine hailed Wilson as a genius making the “weirdest show on TV.” The New Yorker went so far as to run two different odes by two different writers shortly after the show premiered in October 2020. Wilson even got to hire one of his heroes in Orlean—“a major inspiration to me,” he says—to write for the show. How she got involved is a funny story. When Wilson was expanding the writers' room for season 2, he told HBO he’d love to maybe hire someone like a Susan Orlean.
Amy Gravitt, the head of comedy at HBO, suggested that they might as well go out to, y’know, Susan Orlean, Wilson recalls. “I was like, Oh.”
So Orlean came onboard for Season 2 of How To. “First of all, I loved the show,” Orlean explained in an email. “Secondly, I wanted to know how the sausage was made, because it was such a marvelous and yet mysterious sausage.” Still, the idea of becoming his hero’s boss filled John with impossible dread. Especially when he realized that it fell to him to rouse the troops. “I was atomically depressed during a lot of the Season 2 writers’ room, because I felt like I was disappointing a lot of my idols,” Wilson says. “And that's the agony of being in the writers’ room. I'm trying to picture what might happen, but really, the only way to do it is to film it.”
Wilson, who was born in Queens but raised on Long Island, came up with his signature style while working odd jobs after college. He spent time as a school portrait photographer. He taught video editing for broadcast journalism at the New York Film Academy. He did some infomercial stuff. Wilson even worked in advertising for a while, an experience that “really radicalized me,” he says. “I see the way these people think and it's really disgusting to me. I don't know what kind of lobotomy they get in advertising school, but they find bits of pop culture or art that has a soul, and they either try to get the artists themselves to collaborate with them, and if they can't, then they get someone to imitate it and rip the heart out of whatever the art was.
“Once I started to see how that world worked,” Wilson says, “I was like, ‘Okay, I need to develop a style that can never be easily recreated without my direct involvement.”
So, he began posting funny yet nonsensical How-To videos on Vimeo and his website, johnsmovies.com. Eventually Wilson’s work caught the eye of Nathan Fielder, whose own brand of absurdism had made him a star at Comedy Central. After a chance encounter one night in New York, Fielder agreed to help Wilson develop the nascent How To into a show. “I feel I witnessed John becoming both an amazing storyteller and collaborator,” Fielder says in an email. “When we were first developing the series, John told me his process and how it would often take a full year just to make an eight-minute short film. How he would walk around the city alone and film stuff and sort of figure out later in the edit what it was about or what he wanted to say.”
Fielder helped Wilson strategically condense down his production process, especially since they needed to make six 30-minute stories in the time it’d typically take him to make a short film. As they worked together to put together a pilot, Wilson says he and Fielder would frequently butt creative heads, which was to the show’s benefit. “My biggest fear in working with John was that I was somehow going to fuck up what he did, or ruin the charm of his work in translating it to TV,” says Fielder. “He said to me recently that he wouldn't really want to go back to the old way he used to do things. So that felt nice to hear. Or at least I was relieved. I'm just a fan who wants more John Wilson stuff in the world.”
Wilson was already pitching the project around—he says he had even made a pilot for Viceland, which did not pan out. (The episode was called “How to Sell Out.”) Eventually, How To landed at HBO, where it was instantly regarded as unlike anything else on television. Each episode is built out of innumerable hours of footage distilled into a dreamlike narrative. “The editors and myself all have total recall of all the material,” says Wilson, when I ask him how he keeps track of everything. “So if I mention a pigeon with a piece of spaghetti on its back, they know exactly what I'm talking about and where to find it immediately.”
Ultimately, the show is a deep reflection of Wilson and his way of thinking. “John has very specific taste and points of view and things that he likes and things that he doesn't,” says executive producer Clark Reinking, who had also worked with Fielder on Nathan For You. “He’s kind of a quintessential New Yorker in that way. He has a lot of very detailed, thoughtful opinions about the place.”
Where, exactly, did that sui generis perspective come from? Wilson says his childhood on Long Island was defined by a profound sense of boredom. The monotony of the suburbs was instrumental in his development as a filmmaker, in that it forced him to devise his own entertainment. “I used to go to a Blockbuster every weekend,” he remembers, “and I used to dumpster dive all the movie advertisements that they were throwing out.” Young John was entrepreneurial, too. “I'd burn DVDs and make VHSs of all my work that I would sell to the kids in school. I would get the cases from the dumpster at Blockbuster and Hollywood Video. That was my hustle.”
He would film home movies with a Sony Handycam, and eventually went on to study cinema at Binghamton University, where he developed his grimy sensibilities. “It is a very economically depressed, upstate New York town, but the origins of the film school up there are all kind of these legacy experimental filmmakers,” he says. “So I just became obsessed with all that stuff, and there was so much trash up there and empty buildings to explore and shoot in, and I ended up dictating a lot of what I did.”
At one point, Wilson considered becoming an urban planner (“I like density,” he says), but ultimately decided he liked making movies too much. Besides, he reasons, the show functioned as “a container for a lot of things that I'm half good at,” which includes stretching his civic muscles, levying critiques at the dissolution of public infrastructure that’d make Jane Jacobs proud. (See: “How to Find a Public Restroom.”)
And so, given all of this—Wilson’s talent for making the show and critical success it earned—it was something of a shock when Wilson made the decision to end the series. It wasn’t a move that came easy. But Wilson says he didn’t want to risk retreading old ideas—he wanted to bring things to an end while they still felt fresh, to “try to preserve the strength of whatever the work is.”
He decided to end the show with a marching band playing a rendition of “La Vie En Rose” as Wilson delivered a beautiful monologue meditating on life and purpose, and thanked the audience for watching his movies. He had discovered the band during the making of season three, in the most John Wilson fashion: “I was looking on YouTube to see if anyone had found three Pop-Tarts in a pack of two Pop-Tarts. Someone had, and it was like a video with just like a hundred something views.”
He clicked around and learned that person was in a marching band, and came upon a “really beautiful rendition of ‘La Vie En Rose,’ and it made me so emotional when I watched it that I would just play it on loop every day.”
Right now, though? He finds not working a little strange. And he’s not totally sure what’s next for him. Maybe it’s a feature. Maybe he’ll stick to television. I suspect part of the reason John Wilson is so admired is he’s an otherwise normal, thoughtful guy who got to live out a modern-day fantasy in which he received an HBO-sized budget to make art he enjoys making, on his terms. It’s a dream—maybe the only dream, really. Something that feels aspirational and out of reach for most of us.
These days, Wilson often finds himself in rarefied air. He remembers one conversation he had at a party with Succession creator Jesse Armstrong, who also decided to end his beloved HBO show before the audience was ready.
“We both had a very similar sadness where we love what we’ve created so much,” says Wilson, “and we love the people that are part of it so much and don’t want to let them down by concluding it.
“But the best thing you could do,” he adds, “is leave people wanting more.”
Chris Gayomali is a GQ articles editor.
A version of this story originally appeared in the 2023 Men of the Year issue of GQ with the title “John Wilson Goes Out on Top”
PRODUCTION CREDITS:
Photographs By Chris Maggio
Styled By Brandon Tan
Grooming by Melissa DeZarate for A-Frame Agency
Tailoring by Carlos Sanchez at Lars Nord Studio