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John Wilson wants to capture a New York that's both 'timeless and aggressively dated'

ARI SHAPIRO, HOST:

John Wilson goes through his life in New York with a camera, obsessively documenting each day. Those archives are fodder for his show "How To With John Wilson," which is in its second season on HBO. Each episode starts as a how-to and wanders far afield. There's how to make small talk, how to put up scaffolding...

JOHN WILSON: I have a little scavenger hunt list that I start each season with that I distribute to production.

SHAPIRO: One day, his team might hunt for images of tangled cables - another day, toupees.

WILSON: This weird thing happens once you start looking for something. It often just begins to reveal itself to you, and you begin to notice it.

SHAPIRO: The show is full of jokes that won't land on the radio because often the setup comes from John Wilson's narration and the punchline is in the images, like when he says...

(SOUNDBITE OF TV SHOW, "HOW TO WITH JOHN WILSON")

WILSON: You go through a whirlwind of emotions - shock, rage, sadness, panic and finally, acceptance.

SHAPIRO: You see the facades of buildings where the windows and doors are arranged like a face expressing shock, rage, sadness and so on. I asked John Wilson when he realized that the video diary he'd been filming was more than just a private archive.

WILSON: I always had ambitions, you know, for this material to kind of - to be able to offer something for people in the future, you know, whether it's to remind them of how a specific intersection looked or, you know, what the price of something was. You know, a lot of my favorite moments in old, you know, fiction films or documentaries are the parts that capture things that change extremely quickly and fluctuate, you know, wildly. And I always like to jam pack my documentaries with that kind of imagery because it just continues to pay off, you know, the farther away you get from the date that it was filmed.

SHAPIRO: It's kind of extraordinary to hear you say that because over the course of Season 1, New York transformed more than it has in any of our lifetimes as the pandemic shut everything down.

WILSON: Right. And that was like a really, like, kind of tragic but exciting moment for me because I was filming the finale of Season 1 and, yeah, COVID started to just, like, change the way that the city looked. And I - you know, in that moment, I realized that I had this opportunity that I never thought that I would have to be able to capture the city in a way that maybe no other show was prepared to in the moment because I could scale the production down to a single person, you know? Like, I have 40 or 50 people, like, total working on the show. But the fact that, you know, the show is from one POV, the production value doesn't change if you - if it gets down to one person. So I could drift in and out of these spaces, and I didn't really have to worry about hurting anybody else, I guess. It was just me that was taking on all the liability.

SHAPIRO: Is it possible for you to describe what that point of view you bring to the city is, what the portrait of the city is that you're trying to paint?

WILSON: I feel like I get really upset when I see things disappear in New York City, you know, whether it's a certain kind of performance you see on the train regularly or, you know, like...

SHAPIRO: You mean like a break dancer or somebody singing with a karaoke machine?

WILSON: Exactly - or, like, a magician on the train. I really want the show to capture a New York that that feels, like, both timeless but also aggressively dated at times, you know?

SHAPIRO: Yeah.

WILSON: Like, I want it to capture, like, the parts of New York that I don't really see represented in other media. And, you know, it's like I always have this thing when I go to a new city and I walk around, and I just think, like, why haven't I seen this city portrayed like it actually is, you know? Like, it just seems so simple to just film what's there instead of trying to obscure it or dress it up, you know, in one way or another.

SHAPIRO: I wonder, just going through life as a person with a camera on you all the time - setting aside the fact that you're the host of this show on HBO - do you ever find that the effort to constantly document everything gets in the way of experiencing everything?

WILSON: I feel the opposite way. I think that obsessively documenting everything sometimes gives me a reason to go out and experience things.

SHAPIRO: Your friends never get annoyed at you rolling into their dinner party with a camera on?

WILSON: (Laughter) No, I think they've - my friends have accepted the terms and conditions of hanging out with me.

SHAPIRO: (Laughter).

WILSON: Ideally, at the end of the day, I'm the butt of every joke.

SHAPIRO: I think probably the bravest thing you've done across two seasons of this show is present a clip of your first feature film.

WILSON: (Laughter).

(SOUNDBITE OF TV SHOW, "HOW TO WITH JOHN WILSON")

WILSON: It was a Christmas movie called "Jingle Berry," and it took over three years to make.

SHAPIRO: Can you tell us any more about it?

WILSON: Yeah. I feel like I've summoned some kind of demon by invoking kind of "Jingle Berry" here.

SHAPIRO: (Laughter) A seasonally appropriate demon.

WILSON: Yeah, yeah, yeah. Yeah, "Jingle Berry" was something that I don't want anyone to ever see. But hopefully, you know, if somehow a copy does leak somehow that I didn't know about, you know, hopefully I got ahead of how painful it is to watch.

(SOUNDBITE OF TV SHOW, "HOW TO WITH JOHN WILSON")

WILSON: I also screened it for my parents, and my own father told me that it was the worst movie he had ever seen. I was so embarrassed afterwards that I destroyed every single disc that I made. But for some reason, I still hold on to one of them.

SHAPIRO: I feel like with a certain level of renown, you could auction off a private viewing for charity and make some cause that you believe in a lot of money. Like, only you get to watch "Jingle Berry," and you can't tell anyone about it, but, like, millions of dollars will go to this cause that you care deeply about.

WILSON: It sounds like a punishment for whoever wins that auction. It's so bad. It's...

SHAPIRO: How do you bounce back from that kind of utter rejection you describe, where even your parents say it's the worst film they've ever seen, and yet you soldier on? And many years later, here you are with your own show on HBO that is, like, distinctly your vision.

WILSON: You know, it was painful in the moment when "Jingle Berry" failed. But, you know, over the years, it became empowering in this weird way because I realized that that's not what I wanted to do anymore. I didn't want to make the kind of comedy like that. I didn't want to make fictional films. I didn't want to direct actors. I didn't want to do anything like that. And, you know, like, by telling the "Jingle Berry" story, it's like part catharsis for me, but I also just, like, want people to feel comfortable, like, as artists. Like, no one is born as a fully formed artist, and "Jingle Berry," like, to me is an example of kind of skeletons that a lot of artists have in their closet. And, you know, I feel like we all have a "Jingle Berry" somewhere that we're trying to hide from other people. And I think that confronting that and acknowledging that is a healthy first step towards, like, you know, maturing as an artist or whatever you are.

SHAPIRO: John Wilson - the second season of his show "How To With John Wilson" is out now on HBO Max. Thank you so much. It's been great talking with you.

WILSON: Yeah, thanks so much for having me.

(SOUNDBITE OF MUSIC) Transcript provided by NPR, Copyright NPR.