John Wilson was filming the scene on Park Avenue with his handheld Sony camcorder when I met him in midtown for coffee. He was sporting a “Jeopardy” T-shirt, and I thought of how the late game show host Alex Trebek might have loved Wilson’s question and answer style of television.
For over a decade, Wilson has been traveling around the boroughs answering the questions every New Yorker has asked themselves at least once. It began with offbeat short films entitled “How to Clean a Cast Iron Pan,” “How to Live With Bed Bugs” and “How to Remain Single,” before rebranding itself into the acclaimed Nathan Fielder-executive produced HBO docu-comedy series “How to With John Wilson.”
In the show’s third and final season, premiering on HBO and Max on July 28, Wilson turns “How To” into something a bit more personal, reflecting on the making of the show, and tackling some pretty heavy topics like how to like what you see in the mirror and how to be honest with yourself. The aforementioned questions might not have made it as titles to any episodes of Season 3, but their spirit is garishly present.
“I didn’t fully plan to get so personal this season, but it was kind of inevitable,” Wilson says. “As I get deeper into these stories with these real people, I then need to go deeper internally.”
“And sometimes that means going much deeper into the memoir material,” he adds. “A lot of people in my life hear things about me for the first time through the show, which is kind of, like, a strange way to confess or reveal something. But I have a hard time revealing sensitive things about myself normally, so I think the show is a vehicle to do that.”
Prior to the SAG Actors strike, Wilson sat down with PvNew to talk about the production of the show, working alongside Nathan Fielder and what he’s planning to do next with his video-essay media.
So, uh, here’s how to do an interview with John Wilson.
There’s this chicken or the egg thing that happens in my head with each episode. I always wonder, do you go out and shoot video and then come up with the “How To” or is it the other way around?
I kind of start with a title. As I’m writing each season, I’ll just think of a title that sounds good to me for an episode, like “How to Find a Public Restroom” or something like that. The ones I stick with are the ones that have no easy solution, and so you kind of get lost as you’re trying to figure out how to do it. Anything with a solution, I try to cast off, and go to the most complicated.
Then I usually have a small kernel of an idea that’s based off of, like a personal problem — or, like a five second piece of footage I have. Each episode is very different.
How so?
I mean, it always starts with the title, but the way everything unfolds is very unique for each episode. I’ll usually start interviewing people based off of an idea, but then take the first exit I can find and follow that as far as I can. And retroactively make it relevant to the original subjects. But there’s just a big soup of footage at the same time, so in the edit is where most of it is actually written.
And is that you going through all of the footage, or do you work with other editors?
I go through 100% of the footage of myself, but I also have really great editors that do the same thing who give me other ideas. My co-writer Michael Koman — who is also an executive producer — and I will figure out what the strongest threads are, and try to shave away everything that doesn’t support the narrative.
So there’s a lot that doesn’t make it in, just because it is a 20 minute show. But I think there’s something really special about that specific length of time. It kind of forces you to have constraints, and to remove a lot of fat. Even though in the finale of this season, we were able to make it a little longer because there are ambitious themes in it.
Yes, you get really personal toward the end of Season 3. Did you have those intentions from the start, or did that develop along the way?
I didn’t fully plan to get so personal this season, but it was kind of inevitable. I think as I get deeper into these stories with these real people, I then need to go deeper internally to figure out how to relate to them, so that it isn’t just a one-way thing.
And sometimes that means going much deeper into the memoir material, or sometimes into stuff where I’m unsure how it will be received, and am kind of terrified about. A lot of people in my life hear things about me for the first time through the show, which is kind of a strange way to confess or reveal something. But sometimes I have a hard time revealing sensitive things about myself normally, so I think the show is a vehicle to do that.
You mentioned the relationships between you and your subjects, and you’ve gotten into some really weird situations — in their houses, on road trips, even at random conventions with them. Have there ever been times when you’re like, “What did I get myself into?” Or does the camera pose as a safety net?
If I was just walking into these places without a camera, or without having a crew just a couple blocks away, I would feel a bit more nervous. But the camera provides a layer of protection in a way, because people feel they will also be accountable for what they do on camera. Not that they’re doing anything bad, but if anyone were to try —well, I don’t know.
When I went to the energy drink CEO’s house in Season 2, that was genuinely really tense. I was shaking the whole time. This was kind of a bit of a transgression, I guess, but I had people nearby that could hear me in case anything happened.
I try to reduce the crew to just me, so that I’m the only thing anyone is seeing, otherwise they look at other people. So it is a very intimate space. I was a lot more nervous during Season 1, but I’ve kind of settled into it, and it feels very natural. Now, you can tell very quickly if someone wants to be filmed or not.
There are a few instances, though, where people seem standoffish. Do you think since the pandemic people are less available, or interested in talking?
I don’t think anything’s changed. If anything, people are more eager to talk, because they’ve been inside for so long.
How long did it take you to shoot a season? And how much footage do you acquire?
You could say it takes six months, or you can say it takes a lifetime. We shot most of the third season last summer, so it’s been in the edit for a long time.
And why is this the last season? Was it for personal reasons?
I think there are some personal things involved, but it’s very complicated because each of these episodes are very dense, and they involve very emotionally stressful things.
I still haven’t figured out a good way to say this — I just don’t really like to think of it as the end. It may be the end of this project with his name, but I’d rather people not focus on that as much. But it’s like, I’ve been making “How To” movies for 13 years.
Really? In this same format?
Same format. I started in, like, 2011, but it was much grungier, and, like, 10 minutes each. So when I started to think about this as the last season, it became exciting, because I was holding on to a lot of stuff during Seasons 1 and 2 that I was kind of afraid to deploy. It was liberating to be able to finally use all this stuff that I wanted to use and lay everything on the table — the more meta stuff, like the anxiety over how the show was received. We also do hit a point by the finale where, thematically, we deal with very big subject matter that I wasn’t sure how to walk back from, so it was just cool to throw everything at the wall.
So if it weren’t the end, you don’t think you would have put it all out there?
I’m not sure I would have put certain personal things in there, or confronted such big existential themes.
Without spoiling anything specific, in those last couple of episodes, what were the hardest things for you to touch on?
Revealing some of the mechanics of the show and how things are made was something that I feel like we could only do closer to the end, because I didn’t want people to begin to question anything about the truth of the show. Even though it is a minor technical thing, I think once people’s perception of the way that the show is made changes, they’ll watch it differently. And you could say that people can retroactively watch the show differently after something like that, but I don’t know.
It’s like an Oz kind of thing.
Yeah, exactly — you pull back the curtain and see what’s real and what’s not. But everything is still real, it’s just this little thing.
For sure. I mean, you still show New York as New York.
Yeah, and you could say that something like this could go on forever. But for me, it’s diminishing returns after a while. I didn’t want people to begin to see repeat imagery. Even though the imagery will always be refreshing itself, I just didn’t want anything to feel redundant. Especially thematically. Because you can only cover the same kind of topic so many times. But that’s not to say that there’s nothing left. I’m excited about trying something a little different.
What is that for you?
I have some ideas, but it’s gonna be different than “How To” in a couple different ways. It’s more personal.
But it’s in the works?
Well, I’m always, like, writing stuff. And I’m always just shooting stuff. It’s something I can’t really turn off. I’m kind of taking this time right now to reevaluate what the work is doing for me. Because it’s done a lot of good so far. And I don’t want to push it past the point of that.
What was it like working with Nathan Fielder?
We met in 2018 or 2019. He knew my work, and so we just tried to come up with an idea. We pitched it, and they miraculously bought it. It’s been really cool working with him. He taught me a lot, like how to work and collaborate with other people.
That’s not something you were really keen on before?
I was just working alone for so long, and I needed to get used to throwing out a bunch of my bad ideas. And he was a really great guide in that way. But also Michael Koman, who was the co-creator of “Nathan for You,” has been on my show, and he’s really sharp and always challenges me.
Was it your intention for the show to be funny? Or did they bring that to the table?
Our senses of humor are very much aligned. There’s this whole body of work that I did before the show, and I thought that I had exhausted every option before “How To” even began. So I didn’t even think I would be able to make one episode of this show, which is why I have this irrational fear that it can’t go on.
But there was always something comedic about it, because that’s the best way to Trojan Horse a real idea into the world. Even if it’s about civic design, scaffolding or restroom infrastructure —even if it’s bone dry — to me, there’s a comedic way to make a statement. And that’s the kind of stuff that really speaks to me. So I just wanted to continue that tradition somehow.
Do you ever feel like the camera is a part of you, since you’re always carrying it? Or do you ever want the camera turned on you?
I wanted to remove my image from the show, because I didn’t want it to be a vanity project. I feel like a lot of people just try to reproduce their own image constantly. I mean, I’m all over the show in a lot of other ways. But I just felt like I would be the least interesting part of the imagery, so pointing the camera in the other direction is good.
But I still have this camera with me all the time [points to his camcorder on the table].
It’s nice to not have the big camera around as much, because it’s kind of exhausting to carry it around New York all the time. Not to say I won’t bring it out again, but I’m in a much more home-movie phase right now in between projects.
In terms of the show, is there anything else that you want to share?
It might be the last season, but I just don’t want people to feel sad about it at all, if they do. Because whatever comes next is gonna have a similar perspective and voice and stuff. I just think the video essay format is like very elastic, in that you can say whatever you want in there. And I don’t think that’ll ever die.
