This article appeared in the August 24, 2023 edition of The Film Comment Letter, our free weekly newsletter featuring original film criticism and writingSign up for the Letter here.

Photograph by Thomas Wilson/HBO

In January 2013, John Wilson uploaded one of his first short films, an anthrax-laced love letter to New York City life called How To Live with Bed Bugs, to VimeoOver the next few years, he continued to post similar no-budget shorts, each a collage of random New York City–street scenes, shot guerilla-style by Wilson and transformed into parodies of educational films by his endearingly stilted and awkward narration. These are funny (and surprisingly moving) anthropological tone poems, each of which dissects some highly specific aspect of contemporary urban life. His work gradually attracted attention: Vimeo commissioned Escape from Park City in 2017, and 2016’s Los Angeles Plays New York and 2017’s The Road to Magnasanti both played at the New York Film Festival. Comedian and producer Nathan Fielder (of Nathan for You and The Rehearsal fame) took notice and shepherded Wilson into a deal with HBO, resulting in the comedy docuseries How To with John Wilson, now in its third and final season.

Over the course of the three seasons of How To, Wilson has documented all manner of fascinating subcultures and characters in New York, from obsessive devotees of James Cameron’s Avatar to passionate vacuum-cleaner collectors. There is no such thing as a boring person in Wilson’s world, and he allows his subjects to open up in ways that are startlingly humorous, deeply sad, and sometimes both. It’s a cliché that wonder exists all around us, beneath the mundanity of everyday life, and we just have to know where to look for it. How To updates this hoary idea with its gently ironic but sympathetic observations of the world. For Wilson, that sense of wonder is less a matter of childlike awe and more a decidedly grown-up “What the fuck?” How does a restaurant’s sidewalk seating get filled with giant stuffed bears? Why is that man wearing a fishbowl on his head? Is there really a store dedicated entirely to selling supplies for referees?

Amid the ongoing rollout of the final season of How To, Wilson has programmed a series for Anthology Film Archives that combines his filmmaking influences with works by him and his collaborators on the show. Bruce Brown’s 1971 motorcycle-racing documentary On Any Sunday and George Kuchar’s playful diary videos appear in the retrospective along with Wilson’s 2007 student filmLooner, about balloon fetishistsLast week, I sat down with the filmmaker over Zoom to talk about the show and the Anthology program, his approach to authenticity and irony, and the art of capturing the highly specific strangeness of everyday life.

Each episode of How To has a stated subject, but there’s also a deeper theme that emerges gradually. “How to Cook the Perfect Risotto” becomes a look at mortality, because it’s also about the beginning of the COVID-19 crisis. Are you conscious of these ideas before you shoot the episodes?

I usually begin with a title for each episode, and then try to pry it open. I don’t really ever know where it’s going to end up. I write a preliminary script that is more or less a traditional documentary, but then I lean into the different detours we take and try to find something within those diversions that could reveal some deeper truth about the initial problem the subject matter poses.

With the restroom episode [the first episode of season three, “How to Find a Public Restroom”], it quickly became a piece about private versus public spaces and gatekeeping. As I tried and failed to enter certain spaces or film certain events, it started to amount to a commentary about access. There are a lot of things that we try out and discard. It’s like a conspiracy theory—you shave away everything that doesn’t make sense and focus on the stuff that supports your theory, until it almost seems too good to be true. And maybe sometimes it is, I don’t know.

For the restroom episode, did you find yourself being told “No” more often than usual? Was the world more closed off than you had previously realized?

I was pursuing, I think, especially hostile environments, which may have added to the overall frustration. We got access to a lot of places that I never thought we would, but we tried to lump as many of the denials as we could into one narrative. It happens in “How to Work Out,” too, where people at my old college don’t believe I have a show, and won’t let me into their parties or believe I am who I say I am, whatever that means. I only put something in if it supports everything else thematically.

People are surprisingly willing to let you into their homes. How much negotiation does it take to get that kind of access?

During the first season, it was harder to get people on the street to sign releases. By the third season, when our field producers would approach people and tell them it was our show, they would often say, “I wouldn’t sign something like this normally, but for How To, I will.” That was cool.

When I’m in someone’s apartment or house, usually there’s been a conversation before, whether it’s through me or a producer. If it’s someone I first encountered on the street, we try to include that initial interaction and then shave away some of the negotiation stuff. I’m usually very up-front about the nature of the show. If we’re planning to visit someone and they haven’t seen the show, we often tell them to watch it. We want people to feel comfortable being part of something like this.

There’s a moment I love in “How to Clean Your Ears,” when you’re talking to different people about noise issues in their apartments. You have a shot of a man saying, “This is my bed where I sleep every night…” and then the camera pans to the window. Just as he says “…and this is the Myrtle-Broadway station,” a train screeches onto the platform mere feet away. It is clearly a preplanned shot, because you say, “Okay, go ahead,” right before he speaks. How often do you go with what you capture naturally, as opposed to setting up a shot like this?

It’s something I think about a lot, because the show is so dense, and we have so little time to establish certain things. The train shot was something I wanted to be really tight. We were sitting in this bedroom in silence, just waiting for the train to come. I had this shot in mind before we even met this kid; I thought it would be the perfect way to have this establishing line and then an immediate payoff.

I think that happens with a lot of shots in the show. I have a kind of style guide for the camera people that details how shooting something a certain way can let it easily become a joke in the edit, even if it doesn’t feel like it in the moment. If you’re filming a house on fire, make sure you get that, but then pan to something that has nothing to do with the house on fire. Then, as we’re crafting each episode in the edit, you can make some twisted connection between the two. The less sense it makes, the funnier it is sometimes.

In the penultimate episode of this season, “How to Watch Birds,” you pull back the curtain on the show and ask the audience to question how much of what they’ve seen is real. What brought that out at this stage of the series?

I feel like I wanted to swing for the fences with this season, knowing when I started writing it that it was probably going to be the final one. I especially wanted to position that episode late in the season so that people wouldn’t question what they were seeing up until that point. There’s a moment [from an earlier season] that I reveal was fabricated, but it’s minor. I didn’t want to expose that until it felt like we were approaching a climax with the series. Instead, I wanted to make a piece of work that you can point to if you’re ever having a conversation about documentary ethics and just say, “No, look, it’s okay to do whatever you want.” Because it’s tough. I know that there’s no real purity in any nonfiction filmmaking, because you’re always crafting it in some way or another and manipulating what the audience is seeing.

One of the screenings in the series you programmed for Anthology is a showcase for work by the different editors, cinematographers, and crew members on the show. Is there anyone you can give a shout-out for being behind some notable moments from the show?

Yeah. Britni West got that amazing shot of the man sitting on the subway steps that makes it look like the Empire State Building is his erection. That just floored me. I knew we needed to start the season with that shot, because it was so well-composed. LJ Frezza was an assistant editor throughout the show, and he finally graduated to editor for one episode this season, “How to Watch the Game.” Have you seen the work of any of these people?

I’ve seen LJ’s short Nothing.

Yeah, that is a great one. LJ is so great at finding these strange, awkward moments within material that we all know really well. That made him a good candidate for the postproduction team. He’s got a great short coming up—it’s like a Sex and the City edit.

The series includes work by directors like Bruce Brown and Les Blank as well as more underground guys like George Kuchar. What unites these films, in your mind, and how they have influenced your own work?

I just find all of it to be inventive and inspiring nonfiction. They’re films of a certain era, mostly the ’70s through the ’90s, and what defines a lot of them is that they’re earnest portraits or investigations. This is the work that I would like to see more of in the world. It’s what I constantly mine from whenever I’m brainstorming for the show. They’re not ironic in this way that I feel a lot of contemporary stuff is.

Dan Schindel is a freelance critic and former associate editor at Hyperallergic. He lives and works in New York City.