Sorry, something very strange just happened,” the unmistakable, disembodied voice of John Wilson says the moment our Zoom call connects. “I got a very weird package in the mail that I’m trying to make sense of. It’s from the department of waste management. It’s a hat and, uh, there’s no indication of who it came from.”

When I suggest that maybe they just wanted to send him a hat, he says, “That would be really nice. But I’m just naturally suspicious. Because my friends often pull pranks on me and I don’t know it was a prank until years later.”

The creator and star of HBO’s compulsively funny—and occasionally heart-wrenching—docuseries How to With John Wilson has been compared to pranksters like Sacha Baron Cohen or Eric Andre. But as this conversation for a special bonus episode of The Last Laugh podcast confirms, he is operating on an entirely different level.

When Wilson finally settles in for our interview and turns on his webcam, his face is mostly obscured by a semi-circle sound shield that he uses to record the quirky voiceover narrations that run through his remarkable series.

It feels right that I can’t fully see Wilson during our long Zoom talk. Over the course of How to’s six-episode first season, viewers only catch rare glimpses of his red beard and thick black-framed glasses. That’s because the obsessive filmmaker is much more comfortable behind the camera, choosing instead to focus on the everyday visuals most New Yorkers ignore. “I’m the least interesting part of the image,” he insists.

As I confess to Wilson ahead of tonight’s season finale, I got on board his show a little late, partly because it’s nearly impossible to comprehend without watching it. And yet it has become a word-of-mouth phenomenon among the type of comedy fans who obsessed over Comedy Central’s Nathan for You (that show’s creator Nathan Fielder is an executive producer of How to) because it has captured something far more real and honest than the increasingly outlandish pranks of the man who created Borat.

When I reveal that I’ve become an equally passionate evangelist for the show as those who first recommended it to me, Wilson says, “Yeah, it’s really funny, I’ve seen a couple of tweets online from people that have the same experience as you, only when they finally watch it, they hate it and almost resent it because of how many people told them to watch it. So it could go either way.”

Below is an edited version of our conversation and you can listen to the whole thing right now by subscribing to The Last Laugh on Apple Podcasts or wherever you listen to podcasts.

To start, because we’re talking now when the show has been on for a few weeks, what is the feedback that you’ve been getting from people, either in your life or just random people, since it premiered about a month ago?

The morning after the pilot aired a lot of people that I used to date all texted me around the same time. I think just because I speak about my previous relationships in that episode and it’s kind of a revealing episode. It was just like a flood all at once and it was nice to hear from everyone again. But the reaction has been really interesting. Because I would always self-release stuff on Vimeo and the reaction was always kind of predictable. There would be a few die-hard fans that would share it. And for the most part, it would just have a very unremarkable premiere on the internet. And I just wasn’t prepared for it to become a conversation among people that I don’t really know. Originally I would just screen them for my roommates and that was the only real audience reaction I would receive. And then over the years, I would show them at a festival or a small venue, but it’s just been really shocking to see people respond positively to the work, because I was afraid that it was going to be too niche for a prestige TV audience. But it seems like people are really thirsty for something that feels real.

Absolutely. And you spent a long time making these six episodes, right? So it’s this long process of making it and then all of a sudden they’re all released within six weeks. It must be strange to now have it all out there.

Yeah, I’m sad it’s almost over, but it’s been really rejuvenating to see people respond to it online. Because I’ve seen each episode a couple hundred times and I was just so tired of each episode by the end of the editing process. I could barely find humor in it anymore. And maybe that’s just part of the editing process for most people, but it’s been really refreshing to see that, ‘Oh yeah, you know, this is funny.’ And it reminds me of the first time that I watched the assemblies of the episodes and how exciting that felt to me. So yeah, it’s been a long time, but I’m used to spending a long time on these things. Historically I would spend about a year just filming casually to make a 10-minute movie. And with this, we had to obviously scale up. So I had to make six 30-minute episodes in a year and a half or so. And I wasn’t really sure how to do it at first. Nobody was. We had to kind of learn along the way, and we tried a lot of stuff that did not work, but everything you see on screen is the stuff that did.

Is there an example of something that didn’t work that you either wish had or something you thought was going to be special and then didn’t end up making it in?

Yeah, at one point during the pilot, I put hidden cameras inside of a shoeshine store. And I wanted to see what the small talk was like in an environment like that and how that affected the relationship between the shoe shiner and the person with the shoes. And there was one funny part where this one guy didn’t make any small talk with the shoe shiner and then paid and walked out. But he didn’t realize that he had accidentally dropped like 20 bucks or 50 bucks. And the shoe shiner didn’t chase after him to give it back to him. He actually kept it. I thought that maybe that was because he didn’t make small talk with the guy.

It’s interesting you mentioned using hidden cameras because it does seem like that’s really not what most of the show is. It’s you holding the camera and being there, even if we’re not seeing you. But are there moments in the show where people didn’t know they were on camera?

Yeah, a lot of the sidewalk footage was filmed surreptitiously, but after you shoot it, you approach the person and you tell them what you’re filming and maybe even show them the clip and then ask them for a release and more often than not, they sign it.

It seems like that must’ve been a huge part of this. It’s hard to imagine from watching the show that you actually got releases from all these people, but I guess you had to.

Yeah, I mean, it was a colossal challenge. I thought this would have been the biggest hurdle while scaling up, because when I was doing it alone before I never really had to worry about image releases as much because the stakes were so low. So I was worried that image releases would be a big thing that would make something like this aesthetically just impossible, but it actually wasn’t. And this is where all the money and all the time went. People are confused. They wonder how an HBO show could look so pitiful, but all the money and time goes into making sure that everything is real. Because you can fake any one of these shots, but spending the time to find things that you couldn’t ever really invent is the real magic of the show for me.

For me, the magic trick that you’re doing is linking your voiceover script with the images that we’re seeing. And I know that was a hallmark of your short films before this as well. How does that actually work? Do you build up a massive archive of clips that are organized in a very obsessive way? How does that come together?

Yeah, I have a method that I taught to my assistant editors where I like to keyword every shot, where it tells you very plainly what’s in it, like time of day, maybe the season, exterior, interior, sidewalk, there’s that process. But then there’s the process of thinking more abstractly about the material. So I like to have a timeline that is only footage of awnings or street signs or vanity plates or dog shit. Once you have enough of something and you recognize a pattern, then it becomes its own sequence. We have a psychotic amount of footage.

You can tell.

The editors and I each have our own favorite shots, either the most inherently funny or inherently beautiful, just shots that we really want to see in the show. And then once we pick a shot of someone doing something funny, it doesn’t work on its own. So I’ll write a gag leading up to that moment where that’s the punchline. So it’s kind of this reverse-engineered process.

People have been recommending this show to me and now I’m recommending it to people, but it’s hard to describe for sure. And it’s definitely hard to describe why it’s funny. How do you think about that in terms of striving to make this stuff funny?

I think it just so happens to be a comedy, but I approach the work as a documentary first and foremost. It may sound silly, but I do consider this the highest form of documentary in a way. I just wanted to basically invent a genre where I could do all of my favorite things from non-fiction and fiction films. When we pitched it to HBO, we pitched it to the comedy department because people thought the stuff was funny. But I’m not really part of the comedy world, I don’t know many comedians. Nathan [Fielder] is much more dialed into the world of professional comics.

And he came on as a producer when you were pitching it or before then?

He came on way before we started pitching it. I was not prepared to pitch this without someone like Nathan. I mean, I didn’t have ambitions to have an HBO show. My entire career has been this Mr. Magoo kind of thing where I’m just blindly walking from place to place meeting people and I try not to over-plan too much. So Nathan and I met actually by chance a couple of years ago, and the night we met, we just started talking about each other’s work because he had seen something that I did and he encouraged me to come up with a concept for a show and pitch it. And then he set up all the meetings and I went to Hollywood and we pitched it to four or five different places. And HBO obviously had the best deal, I think, because they don’t have any commercials, which is very cool because I don’t like the way that commercials end up turning what should be a single film into like a four-act thing. I really don’t like the way that affects the art. So that’s why HBO was great, but I would have been laughed out of every single room if Nathan wasn’t sitting right next to me.

His show Nathan for You is also one of my favorites. Were you very tuned into what he was doing as well when you met him?

Oh, absolutely, yeah. I was a gigantic fan of Nathan for You before we met. I would watch it religiously with friends just because I thought it was one of the smartest television shows ever made. And I never thought we would really occupy the same reality. But here we are. And he has taught me so much. He is so good with story and obsessed with realism. And he is great when you’re trying to fight legal battles.

The influence of Nathan for You is definitely felt in that first episode, especially in the relationship that you form with this guy at MTV Spring Break. Can you talk a little bit about that experience, how that happened and developed and really became the heart of that first episode, “How to Make Small Talk”?

I went to the travel agent to book a vacation and it ended up being this really wonderful scene where she opens up to me and she is talking about her previous marriage and I just let her talk for as long as she wanted to. I was planning on going to Cancun because that was just another part of my small talk arsenal, you know, to go on vacation so I’d have something to talk about when I returned. And when I got there, obviously there was the MTV thing going on and I was clearly overwhelmed. And then I met the guy in the lobby who was rapping and I realized at that point that he was also there alone. And he was kind of hard to get ahold of after that night because he lost his phone. So I would see him intermittently walking around, but I knew that I wanted to get to know him a bit more and figure out why he came alone, because I thought that was really peculiar. Then we had that conversation on the beach and we both said things that it felt like we needed to get off our chests.

It’s such a powerful and impactful moment, especially when he’s telling you about losing a friend to suicide. It’s just one of many unexpected moments that happened in this show. And I heard you say that it was Nathan Fielder who said he wanted to have at least one moment like that in each episode where you just can’t believe that you got this on film. Which moments stick out to you that maybe, even when you were capturing them, you couldn’t believe they were happening?

Yeah, so we try to have one unbelievable moment in each episode. At least one and sometimes you get multiple. It’s hard to know when these will happen or where to find them, but it’s kind of just a numbers game. The more things you try, the more people you talk to, the higher the probability is that you’ll get something exceptional or honest from someone that is something you’ve never heard before. That’s the biggest rush I get making this work is the thrill of maybe seeing something that no one has ever seen or hearing something that no one has ever heard. And it’s kind of terrifying to think about how much sheer coincidence goes into making something like this because it makes you think that must be impossible to replicate, you know?

Yeah, especially if you’re not really going in with a concrete plan and just kind of seeing where things lead.

We had a semi-formal writers’ room for the show. I wrote down which topics I wanted to focus on and maybe some people I wanted to talk to or some subjects that I wanted to talk about. But it was very loose and I’m amazed that HBO put as much trust in us as they did, because a lot of the time it would be me walking around, just walking into random doors. And there’s a van of people a block away ready to emerge with image releases and stuff like that.

Or jump out if you need help.

Yeah, but thankfully I didn’t really need that much help.

If people compare my stuff to Sacha Baron Cohen’s work, that’s fine. But to me it’s something completely different.

John Wilson

Before we move off the unbelievable moments, I feel like I have to ask about the moment in “How to Cover Your Furniture” that has gotten a lot of attention, which is the man who shows you his foreskin stretching device that he’s created. How did that happen and what was going through your mind when he started showing you that?

It seems like people are reacting very strongly to that. I wasn’t sure how it would be received. I thought it was kind of funny that the episode about covering your furniture had all of the most graphic parental advisories at the very beginning. But I can’t say we didn’t warn you. But yeah, I saw the anti-circumcision billboard in Union Square when I was going to the Petco and I talked with that guy for a while and he gave me the number of the TLC Tugger guy and told me that he made a device that could regrow your foreskin. So I reached out to him and went to his house and filmed that whole scene. So I was already kind of emotionally prepared for what I saw. People ask like, how did you keep your composure or whatever? I knew exactly what I was getting myself into and I also wanted to see it, just because I was really excited to see what this guy’s domestic life was like. I did not expect the pulley on the bed, that was not advertised on his website. That was a homemade device.

That was maybe just for him.

That was for him, maybe not for his wife. But the thing seems to work. I mean, he was a circumcised person and he has a big foreskin now. People asked if it worked and I’m just so confused when people ask that because there’s HD genitalia, you can see it right there on screen. Obviously it worked.

So there have been some analogies drawn between you and Sacha Baron Cohen, I think just because he also interacts with real people. My mother-in-law actually had watched the show before I did and described you to me as an “inverted Borat.” I think by that she meant that you were trying not to expose people in the way that maybe he does, but rather to humanize them. So I was curious what you thought of that analogy. And do you feel like there’s a sort of fundamental difference between what you do in relation to what he’s doing?

I guess people compare it to whatever they’re familiar with. So if people compare my stuff to Sacha Baron Cohen’s work, that’s fine. But to me it’s something completely different. I like to give the microphone to people that usually don’t have it. We’ve had the same diet of TV characters for so long. Whether or not we realize it, we’re just so bored of all these cliches. And even if the person is just like a totally normal person, it is exciting to hear a new perspective or a new idea. I like to give people time to speak in their own words. Everything is just over-edited these days. Even in the new Borat, they had that whole political theater thing with Rudy Giuliani. And I just wish that it wasn’t as over-edited as it was.

You want to see what really happened.

And it just makes me feel like they’re trying to obscure something. I did like that movie more than I thought I was going to like it.

What you’re doing I think is so different because you really are trying to show reality and that’s not necessarily what a movie like Borat is doing. It’s creating a fiction with real moments.

I just want people to feel comfortable when they’re watching my stuff and know and believe that it’s real. I don’t want there to be any of that tension in my work where you’re trying to figure out what’s real and what’s not. Because I feel like that’s what takes the fun out of something that has more of a prank element to it. You’re not sure where the narrative in a Sacha Baron Cohen thing begins and ends sometimes. And so much of the comedy relies on the tension that is produced by a real-life situation. And if you can’t tell if it’s real, the tension disappears and it doesn’t have the same comic effect. So that’s why I just want to start from the same place with every kind of subject and give very clear indications that this is a real person in a real situation. So you know it’s OK to be sad or happy.

The other really unique thing about the show is that you appear almost entirely in voiceover and we get maybe a few glimpses of you along the way, but that’s really not something that I’d seen before. And it’s not something we usually see in shows like this, including Nathan for You where he plays a much larger role. Is that just how you’re more comfortable or why do you prefer it that way?

I don’t want to shoot myself because I feel like I’m the least interesting part of the image. The imagery that we’ve become used to, you expect to have a host to anchor the image. But there are so many more interesting images to be made and so much more visually exciting things to do. But I don’t want to diss anyone that does that per se. I love the way Nathan does it. Louis Theroux is one of my favorite BBC documentarians and he’s always front and center in his stuff.

Billy on the Street also came to mind as someone who runs around New York talking to people, but he’s very front and center as well.

Right, but it’s a different thing. I very much want the imagery to be the star and I just want it to all be really rich and unique. And I want to produce images that haven’t been made before. Because that just supercharges the whole piece for me. I don’t think that we need another dope on camera telling you what you’re looking at, just pointing at stuff. I mean, I’m just a dope behind the camera, I guess.

So I don’t want to spoil the finale for anyone who hasn’t gotten a chance to see it when they’re hearing or reading this. But I think it’s safe to say that the coronavirus starts to creep into the reality of the show. So how did that affect your ability to finish this show and what made you want to make that a part of the show in this final episode?

Yeah, so the coronavirus shutdown started in the middle of the production of the finale and basically every single production shut down. But the beauty of my show is that I can continue to shoot by myself without anyone around. And there’s no kind of dip in production value because it always looked like shit.

You made a pandemic-proof show!

Yeah, I am taking on kind of a lot of liability myself and I didn’t always tell them what I was doing. So sorry, HBO. But it was a very decisive moment for me where I realized that I needed to capture as much of this in real time as I possibly could, because every single day things changed so quickly. And people’s attitudes about what was safe changed really quickly too. Like that whole section where I’m walking through the grocery store and there’s that massive line, looking back at it now, it’s a really fascinating document to me. Because basically nobody was wearing masks, some people were wearing gloves and I realized that the supermarket rush right when the shutdown began was probably the biggest superspreader event of all.

Everyone was doing exactly the wrong thing.

Exactly the wrong thing in really tight spaces. I’m amazed that I didn’t get it. And even the guy at the yard sale who I was talking to who was trying to sell me the bust of JFK or whatever. There were these two twins and I was talking to them in that little back room and asking them about the coronavirus. It was around the 12th of March. And he said don’t worry about it, it’ll pass. And then I pan to his twin brother. And I think in that moment, I later found, he had coronavirus. Because I checked their Instagram like a week later and he was hospitalized. He’s OK now, I still see him around the neighborhood. They’re both fine. But yeah, I didn’t really know what kind of danger I was putting myself in, but it was just something I felt like I had to do.

So now you have this show that really captures New York in a way that it doesn’t currently exist. And I know you’ve continued to shoot footage since wrapping. Do you have an eye towards what you want to do with this footage that you’ve been shooting during the pandemic in New York?

Yeah, I never stopped shooting even though I don’t currently have the green light for another season. This is just my resting state. I just don’t want there to be any gaps in coverage no matter what, just because this is such a strange, precious time in New York right now. And yeah, I have multiple episode ideas that I’m just shooting and some of them are kind of motivated by the limitations put in place by the virus. Who knows how long this is going to go on for, but I don’t want to assume that someone is going to capture everything the right way. I just want to capture it as well as I can, my own way, before these kinds of things disappear. I think that documentary works best as a historical document and I just feel like even if my movies fail as a memoir or a comedy hopefully they’ll at least succeed as just raw footage of New York during a very specific time.

I think you could have a fascinating second season that really focuses on this time and this moment. So I really hope that you get to make it because I would really love to watch it.

That was one thing I was worried about coming out with the show now. You know, the show is almost all pre-coronavirus and I was afraid that people would not want to time travel back to pre-COVID and that people would think it was kind of crass to talk about these really petty things that don’t have as much relevance to the political or social climate right now. But I feel like I was wrong.

There’s something almost comforting about watching these episodes that take us back to a time that feels suddenly unfamiliar.

But then I’ll also have the same anxiety about, will people—once maybe a vaccine is farther along and maybe we’re reverting to normal-ish—will people want to be reminded of this agonizing period that everyone wants to forget? But I’m just not going to stop either way.

Next week on The Last Laugh podcast: Star of ‘Best in Show,’ ‘A Mighty Wind’ and Peacock’s new ‘Saved by the Bell’ reboot, John Michael Higgins.

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