One minute, you’re watching John Wilson explore the different ways New Yorkers protect their furniture. And then, somehow, through a string of connections that makes sense in the moment and only feels like whiplash in retrospect, Wilson’s in a room with a man demonstrating an elaborate and rather unsettling machine which he’s designed to restore his foreskin. In a different episode of HBO’s How To with John Wilson, an investigation into memory aids leads to a sizable group dedicated to exposing how the “Mandela effect” provides evidence of changes to our timeline. Another episode, looking at the omnipresent construction scaffolding in New York, becomes a surprisingly astute sociological survey of the phenomenon and its impact on the experience of the city.

How To is the most unusual, surprising, and frequently the funniest show on TV. Wilson’s unique practice of extensive video documentation of NYC grew out of his time working for a private investigator and his love of the city. He eventually used his voluminous personal archive of footage as the basis for a series of Vimeo videos that were incredibly niche but beloved by all who discovered them (including myself). One fan was Nathan Fielder, who helped connect Wilson with HBO and shepherd How To into existence. The second season of the series is now releasing new episodes, exploring everything from men who hunt down and eat expired military rations to Wilson’s surprising personal connection with a now-infamous cult. I sat down with Wilson for a video call to discuss the new season and how he and his crew put these episodes together. This interview has been edited and condensed for brevity.

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Hyperallergic: You get some old batteries from a mutual friend of ours in this season! It was delightful to see her pop up.

John Wilson: That was so funny. I saw the ad on Craigslist and was at her place in minutes, and I didn’t even know it was her place. That was so weird, but she was still super game to be on camera.

H: I read in an interview that you’d previously discussed, with [fellow show writer] Susan Orlean, a woman who was still holding onto her wedding ring, so it was this weird kismet when she pulled out her ex’s rings during your visit.

JW: Yeah, we wanted to find someone in the real world who had their old wedding rings. We tried a divorcée who had all this stuff laying around, but it didn’t work. And then there was something about the alternate entryway with the batteries, and it so happened that [our friend] had these rings that would work so much better. Sometimes we try something and it doesn’t work, but then the universe delivers in a different way, and it’s way better than what we’d conceived.

H: How did Orlean join your writing staff this season, along with Conner O’Malley?

JW: They’re just two of my favorite artists. I think Conner is one of the funniest people in comedy right now. He’s doing unapologetically inaccessible stuff sometimes. I’d seen him perform a bunch of times before I asked him. And Susan is just, she’s the queen, this amazing journalist and essayist. I’ve loved her stuff for so long, and I was astounded that she agreed to meet with me and be part of the team. I like having Conner and Susan and Michael [Koman] and Alice [Gregory] on the same bill, because I think they represent different parts of the show. Conner and Michael are from the comedy world, while Susan and Alice are really skilled journalists. I want to have both those elements, because the show is equal parts reportage and absurd comedy.

H: So you and the writers conceive of these subjects for episodes and then hunt for material that fits. Do you firm these topics up and then stick to them, or do you have different potential ideas, some of which don’t end up panning out?

JW: Usually the episodes remain what they are throughout the whole production. We try to stick with pretty broad subjects so that you can fit as much under that umbrella as you can. With “parking” it was easy, because that imagery is everywhere. But a lot of the time, the further you get from the subject matter, the funnier it becomes. So we’re never afraid to totally ditch the concepts and try to think as abstractly as possible when wandering around.

H: You and your team shoot a ton of the B-roll. Do you ever use anything you’d shot in your many years of documenting New York before the show?

JW: Yeah, totally. Everything is fair game over the years. I’d say about 90 to 95% of the stuff in Season 2 is all-new material, but you do have to dip in and out of the archive sometimes if you’re looking for a difficult shot or if there’s a historical anecdote you need to flush out.

From How To with John Wilson

H: Do you have any idea how much footage you have stored?

JW: I don’t. Thousands of hours, just days and days of footage. All the tiny B-roll snippets I alone shot for this season total like 20 hours or something. It’s overwhelming. I’m really bad at numbers like that. I should probably ask my assistant editors for that answer, because you’re not the first person to ask.

H: Do you have a method of organizing your personal footage?

JW: Yeah, they’re all in folders sorted by days [they were shot on], and I’m constantly referencing what I did on that day. Within that day, I’ll make selects of all the funniest, most interesting B-roll that could fit anywhere. The assistant editors do a lot of that stuff for me as well. They tag everything and they lump it into folders for the editors and try to interpret the footage and figure out what episode it should go in.

H: How much of the material you find is stuff you hear about on the news or an app and then actively seek out, versus things you see when you have the camera with you as you go about your everyday life?

JW: Sometimes Citizen or Craigslist will bring me somewhere, but a lot of it is just bumbling around. I make appointments to meet people, but that’s usually only after I’ve entered some rabbit hole.

From How To with John Wilson

H: Do you think the pandemic and lockdown have affected people’s receptiveness to being filmed?

JW: I feel like people still just want to tell their stories. I thought it was going to be a big change in one way or another, but it’s honestly not that different. I thought COVID would make people not want to talk to me, but that wasn’t the case at all.

H: That’s heartening to hear. Did COVID pose any other kinds of obstacles during production?

JW: We had a COVID compliance person with us the whole time, and it wasn’t as oppressive as I thought it would be. We were in Vegas around thousands of unmasked people in these massive casinos, and nobody on production got COVID. It was this weird sweet spot after the vaccine came out but before Delta.

But there was one guy who had his leg hit off by a motorcycle, then had his leg preserved. He was from Canada, and had to fly down with his leg in his backpack to talk to us. He had no papers for it or anything; he had to prove to customs that it was his leg, and it took forever. And then he finally got to New York and met with us in Prospect Park to do the interview. And upon returning to Canada, he had to quarantine for two weeks in a hotel. He was taking a ton of time just to do this thing for us. And I don’t always talk to people before I meet them, a lot of the time production sets up stuff. There’ll just be a casting call for someone, like an amputee, and that will yield some people, and we don’t always mention the name of the show. So at the end of the interview, he was like, “Alright, thanks. What was this for?” I just think it’s really funny that this guy took weeks out of his life to fly internationally and didn’t even know what it was for. That maybe speaks to the eagerness of people to get out these days.

H: You told Vanity Fair that you have a promotional billboard for season one.

JW: Yeah.

H: How?

JW: It’s not that big when it’s all folded up! I was looking at the billboard in Times Square during season one, and I started talking to some scaffolders by it. And I was like, “Who’s in charge of the billboards?” And they’re like, “Oh, it’s actually this office in this building.” I went to the office and I’m like, “What do you do with them afterwards?” And they’re like, “Oh, we throw them out.” I was like, “Oh, what a shame. Can I take it?” And they’re like, “Okay, yeah. No one’s ever asked before, but sure.” And now I have this big vinyl mess in my basement, and I realize it can serve no purpose outside of Times Square. For some reason I thought it would be cool to have, but it’s basically trash. I can’t put it up anywhere.

From How To with John Wilson

H: You mentioned that they said no one had asked about that until then. I feel like “No one’s ever asked before” could be a slogan for the show. You’ve been doing this for over a decade. What kind of process made you so comfortable talking to strangers?

JW: It’s a constantly evolving one. I try to expose myself immediately, and I think that has a way of making people more comfortable opening up. I don’t always put it in the show, but I do have very long conversations with these people where I am often admitting a lot of stuff and insecurities from behind the camera. I also watch a lot of trashy reality TV, and when I’m watching a show on HGTV or something, what I want more than anything is to ask the subjects any personal question whatsoever. I’ve worked in so many environments where I was filming someone talking about some product or whatever and there was a PR person behind me. All I wanted was to ask them something really personal, and I just couldn’t. And so in my own work, that’s all I want to do.

H: You talk in one interview about how you think that in some ways, the format of the show resembles social media. But I feel that, since you’ve been doing this for so long, it’s more like the internet caught up to what you do. You’ve documented prolifically in a way that most people didn’t use to, but now, thanks to smartphones and social media, more people also do that. So their feeds create their versions of your style of montage.

JW: I think that’s hopefully why it speaks to people. I like to narrate in the second person just to include the viewer. And I also absolutely want the material to look like something you could shoot yourself. Growing up, the most inspiring stuff to me was always what felt most approachable, the stuff I felt like I could leave my house and just do, without any restrictions or crew or anything. I want to encourage people to continue to document the world around them, and not necessarily have some kind of performance in the center of it.

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New episodes of How To with John Wilson are currently premiering Fridays on HBO. The show is available to stream on HBO Max.

Dan Schindel is a freelance writer and copy editor living in Brooklyn, and a former associate editor at Hyperallergic. His portfolio and links are here.