John Wilson Obsessively Trawls Craigslist’s Free Section in His Spare Time

by Madeleine Connors

John Wilson
Courtesy of HBO

If you want to get in touch with John Wilson, he recommends posting an ad on Craigslist’s Free Stuff section, where the documentary filmmaker is something of a regular. “That’s not completely true,” he clarifies with a smile on a recent afternoon. “But it’s something that I think is really funny. People will sometimes post stuff on there, knowing that I’ll look at it. I take the bait almost 100 percent of the time.”

Over Zoom, Wilson—who shot to cult fame status when his irreverent comedy docuseries on HBO, How to With John Wilson, was released amid the second wave of the Covid-19 pandemic in 2020—tilts the camera to reveal his most prized Craigslist find: an archive of beauty pageants on VHS. It’s the kind of slow reveal that Wilson is known for in his series—but this time, the peculiarities of his own apartment are on display instead. Wilson explains that when a former beauty pageant contestant was relocating from California to New York, she didn’t have room for her VHS library of past on-stage highlights. It was a perfect find for Wilson, who self-describes as a “sucker for any old VHS tape that has a home-recording look to it.” Wilson tells me he’s currently treating the footage as an anthropological artifact, studying the commercials in between the pageant broadcast. What will become of this beauty pageant archive?, I ask him. Wilson says he doesn’t know. “I haven’t done anything with it. I think it’s kind of weird that I have them, still.”

Whenever Wilson opens up his web browser, he involuntarily finds himself on the Craigslist free section, perusing ads of the discarded and unwanted in New York City, where he lives. (“It’s kind of relaxing,” he adds brightly. “I like the window into New York it gives you.”) Zillow has become one of his regular online haunts, too—a place where he spent most of his time during the pandemic. “I love these spaces in New York that almost feel like production-designed versions of New York,” he explains.

That might explain his strange fascination with the Craigslist free section: where others see junk, Wilson sees a story. The very same philosophy could extend toward the success of his hit show, where the filmmaker creates tutorials from interviews with strangers on the streets of New York City, transforming the mundane into something new and exhilarating. The show was met with praise from critics and audiences alike when it first aired last year, even garnering a coveted 100 percent score on Rotten Tomatoes. “It’s nice just to see that anybody cares at all,” Wilson says of the series’ success. “I just find it so heartwarming that people also have these same kinds of anxieties and insecurities about certain things.” Fans of the show will be glad to find out that season two’s premiere isn’t far off—a new episode airs on November 26, after Wilson spent much of the past year filming. He describes season two as “More of the same. Just me, Mr. Magoo-style walking about New York City, and it’s a lot more ambitious at the same time.” Despite his accomplishments, Wilson, who has documented the minutiae of his life for the last decade, remains low-key and self-deprecating. “To me, the story hasn’t changed. I just have a budget now.”

The show’s first season was so well-received, even the subjects he interviewed were interested in showing up for another round. “Now that there’s proof of concept, they understand the tone of the show. They understand that I want to give them a platform to deliver their message and keep their message intact.” The design—and charm, Wilson might argue—of his show lies in the fact that the filmmaker is constantly offscreen, giving the focus to the subject instead. In a notable example from season one, Wilson watches a New York Soccer Referee Association dinner devolve into utter chaos over a rigged raffle; the viewer only sees Wilson briefly in the reflection of a mirror. (“You already get enough of my voice and the rest of my life in the show; I didn’t want you to have to stare at me,” he explains.) Still, these days, Wilson is approached by fans on the street regularly. “People recognize me,” he adds. “Usually, they have nice things to say.”

It makes sense that the director would explore the afterlife of junk on Craigslist, given the sentimental gaze he bestows upon the ephemera featured in his beloved documentary series. “It’s months and months of endless scrolling to be able to find a lot of this stuff,” he says while rifling through screenshots of Craigslist ads he’s saved on his desktop. “Some of it is not really that funny, but it works. A lot of people save condiment packets.”

A collection of John Wilson’s favorite Craigslist Free Stuff section advertisements.

Courtesy of John Wilson/Craigslist

Beyond the voyeuristic thrill of looking at free stuff, Wilson believes there’s an emotional core to these people’s belongings, too. “People have an opportunity to tell their story. Sometimes there’s a lot of pain attached to these things,” he says. “And there’s a therapeutic element to it that gets them on the site, to begin with, instead of just tossing it.” To illustrate his point, he looks to an ad for a single AirPod. The caption reads: “Alone is totally useless.” “Some of it is very poetic,” he says. “It’s got that baby shoes, never worn feeling.”

In another ad, two partial cartons of American Spirits cigarettes are advertised as being from a “smoke-free home.” And an ad for 100 free Kirkland muffins reads: “Unfortunately, my girlfriend broke up with me this morning, and I honestly just don’t feel like celebrating.” “I don’t know if he was going to share them with his girlfriend or [what],” Wilson says. “The oversharing is what I find so interesting. The ones that stick out to me are those that have a strong opinion about the object or a very personal history.”

Wilson plans to take the collection of screenshots he’s been curating for the past decade into a book that will be released with Topos Bookstore, a local publishing press. “I just don’t want it all to get lost,” he says plainly.

When asked about memorable Craigslist encounters, Wilson explains he once tried to obtain a Pier One Imports gift card that had a value of $1.75 on it. “They kept posting it. And in the posting, they kept acknowledging that Pier One may not even exist anymore, but if it does, this might be of use to somebody,” Wilson says. After an attempt to retrieve it, he was denied. “They were picky about who they wanted to give it to.”

The beauty of Craigslist, much like how Wilson sees New York City, is that there are no dead ends, no junk—only people with stories to tell. “I feel like there’s this X factor to the kind of people who use it that makes it interesting. It hasn’t changed for so long. I love that. It provides the purest cross-section of New York. I also love that it’s both the first and last resort for a lot of people.”

Wilson believes that what people are trying to part with often can reveal a beautiful truth about their past, no matter how undesirable the object may seem. “When someone gives you a tiny window into their personal life like that, and you show up, and tell them that you’re a documentarian and you make movies about everything you do and ask them why they’re getting rid of this object, they tend to want to talk about it,” he says.