Premiering at the tail end of 2020, How To With John Wilson was one of the most joyful, unexpected shows on television, both a period piece about the (mostly) pre-COVID era of the city and a poetic ode to the enduring weirdness of NYC. It was a testament to the keen eye and unrelenting curiosity of documentary filmmaker John Wilson, who serves as writer, director, cameraman, producer, and narrator, that he and his team (which includes Nathan Fielder, Michael Koman and Alice Gregory) were able to weave hundreds of hours of random footage taken (mostly) on the streets of NYC and twist them into compelling narratives with emotional beats.

The second season of the show, which sees comedian Connor O'Malley and journalist Susan Orlean joining the writer's room, premiered on HBO at the end of November, and it's just as compelling, hilarious, and probing as the first. In it, Wilson explores the complexities of becoming a landlord; draws out the connection between a cappella and cults; learns about the balletic chaos and choreography of NYC parking; gets drawn into an Avatar support group; and comes out as an energy drink enthusiast.

After the season premiere, we spoke to Wilson about following up his critically-acclaimed first season; how much time he spends filming around the city; the joy in finding community in niche pop culture; how he gets people to open up on camera; and his killer Keith Raniere story. Note: there are "spoilers" for season two, though the show is so unusual it's kind of hard to spoil.

This interview has been edited for length and clarity.

There's that saying: you have your whole life to write your first album and only a couple months to write your second. Did that feel apt for the second season of the show? Did you feel like there was a measurable gap between the two seasons or was it like a fluid continuing project? I've never heard that before. It's not saying anything good or bad about the second album, it's saying that things move very quickly once you...

Yeah, you have all your accumulated life experience up until whenever you make your first big project, and then you have to follow it up immediately, and now there are maybe outside expectations attached to it. Yeah, I think that's cool. I feel like this season had to happen in almost half the time that the first season did, and on top of the whole life thing. We had a much, much faster turnaround time for the second season.

But everything from my whole life, past and present, is still fair game. And that's kind of an endless well for me. And I think there are a lot of different elements that sustain the show and make it easy to reproduce, for me at least, where there will never be any shortage of people in New York who are willing to just bear it all, or just these little tiny communities. And I will actively keep engaging with it, and my life will always be a part of it. And I still have other weird stories from childhood that may resurface at one point.

There's something about the speed of doing the second season that really intimidated me at first, but it was just so much fun. And I felt so much more confident crafting each episode, because I was so long in season one. And I had no idea what the show was supposed to be, but thankfully Nathan Fielder, and Michael Koman, and a bunch of other people really helped to shape everything. And that was just so important.

In general, how much of the footage is new versus old? And do you have any internal rules about how much you're allowed to use footage that you've already banked versus going out to get new footage? Well, I want every single image you see to be new to you, I don't want it to really have appeared anywhere else. That's the rule. I was afraid after season one that none of our back catalog of footage from season one would be usable because of the new COVID imagery around us. But that just wasn't the case. There's a handful of shots in season two from season one. So it was backwards compatible, because a lot of the stuff in season one, there's a lot of shots of just a single person, or a single object.

And I realized that COVID New York has elements of the pre-COVID as well. So it's kind of seamless. But we shot the season with the hopes of having 100% all-new footage. And I'd say about 95% of it is. But sometimes in the edit, when you're looking for a rare shot to fill out this long poem, whether it's a vanity plate or something, you have to sometimes just go deeper into the archive because we only really scratched the surface with the material from season one as well. There's just still so much on the cutting room floor.

I know that you have a team of other people going out and doing some of the filming as well, but what percent of your time, your week, are you going out and filming when you are actively working on the show? It's usually a hard eight hours during formal production. I get up, and sometimes we have something scheduled for that day. Other days I'm just wandering around and people follow me in a van. And so I shoot the first unit stuff where I'm engaging with people and following different threads.

But then we have four teams of second unit people just roving the city every single day for eight hours a day and then at night. So I have to shoot during the day and then I immediately come home to my remote office I have in my apartment, and I download 100% of all of the four second unit teams' material. And then I just power scan through that all night making selects to put into different bins for different episodes, and just take my favorite moments from each second unit person's day. And then I go to sleep, and then I do that again in the morning. But in my time off, during the edit, I don't have my camera around me as much. I always have my iPhone with me, so I'm never without some way to capture what I need to.

So by the time you all are going out to film, have you already crafted and broken what the story for each episode is? Not really. We have a bunch of vague ideas and people that we might want to talk to, but then inevitably something unexpected happens with a subject. And that moment, whenever it falls in production, we then have to decide whether or not that's going to fit in this structure, and whether or not we should build up to that.

I'm trying to think of something that we would have scripted. I mean, like the MRE guy. [Editor's Note: The Meal, Ready-to-Eat guy appears in the second episode of the new season, "How To Appreciate Wine."] That was something that Connor O'Malley came up with in the writers room when we were just talking very openly about what wine is, and eating all the stuff. And he was obsessed with these YouTubers, and we found one. That's an idea of something where we'll script it beforehand and then go in to see what happens there. And then his parents just happened to be there. And his mom delivered this really funny anecdote about eating an expired Slim Fast. And maybe we wouldn't have used that segment if that didn't happen, but whenever something surprising happens we usually try to put it in.

The same team from the first season is back. You, Michael Koman, and Alice Gregory were credited with writing most of the first season, but now there are two new people in the writer's room, and it's...Susan Orlean and Connor O'Malley. And I did a double take when I saw the press release come out a couple months ago about that. How did you end up working with them? And how did they contribute to the season? Yeah, I actively pursued them. They're just two of my favorite artists, and Connor's just doing such amazing things with comedy. And Susan, I've just been a fan of for so long. I asked Connor and he was cool with it. And then I kept asking HBO if we can get someone like Susan Orlean, and they were like, "We could just ask Susan." And then I was like, "Oh, okay." Because I thought that she would've been past that point in her career. I hadn't really been keeping tabs on her or anything. Then we just met up, and we all just went into the writer's room together. And the reaction that you had is very much the reaction that I was hoping for when the credits role, because it seems like such a schizophrenic mix of all of these different things.

But I feel like they each represent a very serious part of the show. Like this kind of absurdist comedy, but also very poetic kind of nonfiction. And Alice and Susan are both journalists, and I really love just spitballing with them about subject matter. Alice Gregory, one thing she brought to the table was the wildlife refugee thing, the confiscated wildlife place [Editor's Note: this happens in the episode "How To Throw Out Your Batteries."] That was something that she knew about, I had never heard of it. When we got to that point in the script, when we're working through what batteries are, then it's like, okay, we have to go to this place. Why don't they throw this stuff out?

And Susan was funny. It was funny in the wine episode where she had a more formal knowledge sometimes, but then we would always just go back and forth between the absurd take on it. So much of their contributions are just the conversations we have about each subject and what they mean to us. And during the batteries episode, the conversation was just all about these objects that we all have, and why we have them. I remember Susan was talking about wedding rings and stuff like that. And I just happened to find someone who was holding onto their wedding rings.

Had you put an ad on Craigslist looking for someone to talk about their rings? No. The person in the batteries episode who I got the batteries from Craigslist from, who had her wedding ring still, that was just, I'm on Craigslist once every hour just looking at whatever. And I contacted her and I went to go meet up with her and it turned out that it was an acquaintance. I actually knew her. I mean, I didn't say that on the show, but she was a friend. And I had never been to her apartment before. I was like, okay. And then basically, I interviewed her and I didn't even realize that she still had her wedding rings. And it was just such a weird moment, because it was something that we had roughly conceived of. I haven't got any better at telling this story...It's such a weird thing to roughly conceive of something in a room and then to have it just kind of come to you in the real world, just through trial and error.

Last night, I decided before I went to sleep that I was going to watch episode five ["How To Remember Your Dreams"], because I thought, oh, an episode about dreams, that would be the perfect thing to ease me into bed. And instead I found myself meditating on all things Avatar, and more pointedly, just the way pop culture can help us find community. Yeah, so I think that, especially with the Avatar people, that's just so much of the fun of the show, is finding just how people form communities in the smallest, most intimate kind of niche ways. And when I met that guy at the comic shop and he told me that there's this group of people that meet up that celebrate Avatar, it's like, I love being able to have access to these really intimate spaces where people bond over this thing that you've never thought about for more than 10 seconds in your whole life, but it's their entire life. And I love how these environments make you rethink your own kind of relationship with the subject, or your own prejudices. And I really want it to just be the beginning of a conversation, even if it is something as weird as Avatar.

Thinking about that room and the way those people revealed these intimate things about themselves, this happens a lot on the show. I'm thinking about people like the casket guy with his hunting room, or even the woman in the season premiere who started telling you about her former tenant with the hairbrush and the toilet. I always assume that I would be more guarded if someone pointed a camera at me. But I feel like one of the things that's so fascinating about the show is how much people reveal of themselves. Do you usually find that people naturally start letting these stories out, these intimate things about themselves, despite them knowing the camera is there? Or do you have to coax it out of them? There's this weird kind of thing that happens once the camera's out. And it's a person-by-person thing how the camera will affect their behavior and the people around them. But I can tell, just within a few seconds, whether or not I'll be able to go on a ride with someone. Sometimes people are very kind of uptight and they're not really sure how to behave, but after time they open up sometimes. I have a hard time on camera sometimes, too. And I don't always feel super comfortable, but I find that I try to gravitate towards people that are more comfortable than I am on camera.

And some people are just naturally who they are, like the lady who was showing me the apartment with that nightmare tenant. I could tell immediately that she just had a very confident deadpan, and the way she delivered that whole story was just perfect. I try to avoid the people that seem like they're performing in any way. I feel like I can also detect that pretty quickly, whether or not they're trying to put on a show. And the people that make it into each episode are usually just naturally earnest people. I mean, sometimes they are exhibitionists, like the energy drink guy. [Editor's Note: Bang CEO Jack Owoc appears in "How To Appreciate Wine."] And his performance is very much part of what makes him authentic at the same time.

So I like eccentrics of all stripes for those reasons, but I feel like once people have the opportunity to tell some story that they're not able to tell anywhere else, they get really excited about it. And, sure, context changes a bit in each episode, but I still feel like I'm giving them a platform for whatever it is they're saying. And I try to just be respectful of that.

So many of the episodes are these bizarre, winding roads where you don't really know where you're going to land by the end of it. So you start off with an episode about wine, and then you end up with this crazy turn with Keith Raniere. You have lightly included lots of stuff about your own life, like with everything happening at your apartment in the premiere. But in terms of this incredibly crazy NXIVM story, were you hesitant about revealing so much about your own past? Yeah. I feel like I had the NXIVM story in my back pocket for season one, but I didn't think people were familiar enough with me, or with Keith Raniere at that point, to deploy it. But then after The Vow came out I realized that, I think enough people would have that kind of aha moment when I reveal it in the show. But I was also really resistant to including my a cappella stuff in the show, just because I think it is something that... I mean, I did have a good time doing the a cappella stuff when I was in college, and I think it totally served a purpose socially for me. But I felt like I could have lived a long happy life without ever having to publicly acknowledge my collegiate a cappella career.

But when we're in the writer's room, one of the most mortifying anecdotes from my childhood will come up, I'll just say something, and then Michael will be like, "Oh, well, that has to go in." And then we, as a group, just try to work it in. And I tense up, I cringe when I watch it sometimes, but I feel like that's a small price to pay for making other people feel comfortable making confessions like that in their own work, or in their own life.

You're willing to put yourself out there in a similar way that you're asking other people to. Exactly. And I'm really being honest in each episode when I'm talking about how I used to drink energy drinks all the time, or how I used to be into a cappella, or how I genuinely had post-Avatar depression in the same way that these guys did in the support group. It almost felt like Avatars Anonymous. It felt like an AA meeting.

The other AA. Yeah, the comic book version.

This is my last question, so I've got to ask: what's the plot of Jingle Berry? [Editor's Note: Jingle Berry is Wilson's first feature film, as mentioned in the episode "How To Throw Out Your Batteries." He is not proud of it.] Oh, my God. Yeah, that's another thing where I feel like I'm summoning some evil spirit by invoking this mortifying part of my childhood. The plot of Jingle Berry...I really hope no one ever finds it.

Is that really the only copy in the safe, by the way? Yeah, but I don't know what friends may have done with copies that they had, because I know that there were a couple other people that worked on the movie. Anyway, the plot of Jingle Berry: a young kid wants this popular toy for Christmas, but his mother is really sick, and there is an evil real estate magnate trying to turn his basement apartment into one of his franchised seafood restaurants. And then he enters a Christmas house decorating contest to try to win enough money for his mother's surgery and for the toy. But then he meets this homeless guy who turns out to be Santa. It's trash.

Oh I don't know, this sounds like it has remake potential. If people want to run with that, that's all I'm going to give him. You don't want to remake it.

This is a jumping off point. Well thank you so much for talking to me today. Yeah, thanks for asking what Jingle Berry is. You're the first person to ask that, so it's cool. But I'm telling you, you don't want to see it. It's not cancelable, it's just a low simmer, cringe the whole time. That's all I can really say about it.