The most recent episode of How To With John Wilson opens with a simple question, as all episodes of the brilliant HBO series do: How does one appreciate wine? It ends up revealing that John Wilson, the nasal-voiced host, was a member of a college a cappella group that attended a conference hosted by Keith Raniere, the now-convicted cult leader behind the group NXIVM. Wilson, who has always come off as exceedingly mild-mannered, helped to stage some singing-group rebellion and tried to out Raniere and his associates, including Smallville actress Allison Mack, way before the rest of the world caught on. (NXIVM, which branded women and forced them into sexual subservience, was the subject of two 2020 docuseries, The Vow and Seduced.)
When How To With John Wilson debuted last year, it quietly emerged as one of the most beautifully perceptive shows on television-half bizarre man-on-the-street observation, half heartbreaking soliloquy about the city of New York. In the second season, which has thus far released two installments, Wilson discloses more about his own life while still introducing the audience to corners of the world most would never think to explore. In the premiere, for instance, Wilson’s hunt to learn about investing in real estate somehow leads him to a ventriloquist. The wine investigation, in addition to revealing Wilson’s NXIVM past, brings him to a man who loves to sample nauseating-looking military rations, aka MREs, from decades past.
This season, Wilson brought on an all-star team to work with his writers, including the wild man of alt-comedy Conner O’Malley and New Yorker journalist Susan Orlean, who is best known for the nonfiction book The Orchid Thief, which inspired the 2002 film Adaptation. Thrillist spoke with Wilson about his staffing goals for this season and his own NXIVM experience.Thrillist: The pairing of Susan Orlean and Conner O’Malley as writers on the show broke my brain just a little bit in an amazing way.
John Wilson: That was the desired effect.
Can you talk a little bit about expanding the writers’ room?
Yeah, the first season, it was just [Late Night with Conan O’Brien alum] Michael Koman and [journalist] Alice Gregory and I, and that yielded some really great stuff. But I really wanted the second season to feel like it was on steroids in one way or another. Conner is maybe my favorite person in comedy right now. Susan is a legend who I’ve been obsessed with for most of my life. Saturday Night was one of my favorite books ever. I used it. Koman and I would reference it just in terms of the portraits that were in that book and the simplicity of it in Season 1.
So when I was staffing up for Season 2, I asked HBO, “Can we get someone like Susan Orlean?” I kept saying that because I thought she would be past the point in her career to even humor something like this. [HBO executive] Amy Gravitt was just like, “We could just ask Susan.” I was like, “Oh, okay.” I was really intimidated at first, but we just linked up and she was super into the first season. We just went into the writers’ room, and it was really cool.
How does the writers’ room work? Where do you start with each episode?
It’s a very strange process. We have a formal 13-week writers’ room, where I have this list of subjects that I’m obsessed with. We just usually pick the ones that don’t have an easy answer, like “how to throw out your batteries” or “how to find a spot,” something that there is no simple solution to. Then we just spitball and write up a script of maybe potential people we could talk to that are maybe a couple degrees away from the subject.
For the batteries thing, Susan had mentioned that she had a friend that held on to her wedding ring and she didn’t know what to do with it. I was like, “Whoa, okay.” That is really something that I personally don’t have any relationship with, but I can imagine it’s super hard. So we penciled that into the script. Then I’m randomly going to pick up these batteries off of Craigslist. This woman just delivers this moment where she talks about how she has these wedding rings. That was so weirdly serendipitous, but you roughly conceive this stuff and then it shows up in real life and you are in disbelief in the moment. It’s really exciting. Or Conner really wanted to do the MRE thing in the wine episode. So we wrote that in. There’s stuff around the middle of each episode, where we just plop in and it’s not like I meet them on the street or something. Clearly this was prearranged. So there was a lot of that stuff. Then I try a bunch of stuff, but then I always just get sidetracked. The ending to each episode usually just becomes whatever the most interesting, shocking diversion was throughout this extremely weird process.
Like meeting the Bang energy-drink CEO in the episode about wine-
Yeah, exactly. Yeah. That was one of the most exhilarating afternoons of my entire life.
I did have a question about the Bang guy. He also seems a little cult-y. Can you talk about the irony of ending on that conclusion?
That’s just what I loved about it so much. I tell the whole NXIVM story. We have the buffer of time, and today we can see what was going on, with full clarity, back then. I really meant it at the end of the Bang section. This is only the beginning, maybe. Who knows? This could be the first chapter of something that in a decade could be something that happens. Who knows? It was super nice of him to let me in and just show me his world. But I didn’t want to be too ham-fisted about any connections with Keith or anything because you may see it as I’m doing the same thing again. I also am embracing a part of myself that I was embarrassed of before. So it’s this big mix of all these irrational things that somehow make me feel better.
Did you always know you wanted to tell the NXIVM story in the context of the show? How did you get from wine to “This is the right place to tell this part of my story”?
It really hit when I was on the boat with those people, like it’s portrayed in the show. Why am I just agreeing with these people? Why do I want to fit in? It’s a story I’ve always had in my back pocket. I think I danced around with the idea of somehow trying to fit it into Season 1. It didn’t really fit in. Also, I feel like NXIVM fever really wasn’t where it is today. I’ve been sitting with this story since 2007. I felt shame for so long because I was like, “I’ve embarrassed my a cappella group, I’ve embarrassed my parents, I almost get kicked out of school. Nobody understands that this guy is evil.” Then, when the tabloids started picking up the story, I started to get this rush and I started to watch it snowball. I realized, “Okay, now is the time to do this.” It was a real catharsis.
What was that catharsis like?
It was difficult at first. I would talk with Michael Koman or even Alice and Susan and Conner about it. I wasn’t sure that I wanted to invoke my a cappella days. There’s a lot of stuff in this season that I thought that I would be able to live a happy life without having to reveal.
Like “Jingle Berry,” the embarrassing film you made that pops up later in the season.
It’s like I’m summoning Beetlejuice. It’s only going to do bad stuff for me. I didn’t have to say any of this. But it does feel good knowing that the viewer might be able to relate with that, in some way or another. I’m sure so many artists have a “Jingle Berry.” They have this awful thing that they want to erase from the face of the earth. But you can’t let go of that part of your life for some reason.
Did you worry that people might try to Google the Binghamton Crosbys and try to find your singing?
Yeah, I’m horrified. I’m sure they’re going to find some embarrassing shit, but I tried to get ahead of it by acknowledging how painful it is for me to admit it.
I wanted to ask you about the personal element of this season. Why did you want to start this season with your landlord, who became such a prominent character in last year’s finale?
She asked me about buying the house not too long after the season finale. So we don’t really pick up the day after, but it’s as close as I could get, because there was just a big dead zone during the pandemic where nothing happened. That was the first big thing in my life that I was struggling with right after the risotto episode. One of the No. 1 questions I get about the show is “How is she doing?” It is going to be such a relief to just have that in the world and not have to explain anymore.
Have you kept in touch with her at all since she went to Vegas?
Well, you might just have to wait to see the finale.
The lingering question I did have from the first episode is: Do you have a tenant?
So have you more formally embraced the idea of being a landlord since you finished the episode?
I’m not like a NIMBY person-or a YIMBY, actually. You know the YIMBY community? It’s people who are pro-development to increase property value. I’ve embraced it insomuch as I need to make my tenants life’s nice. I don’t want to put them on blast or really say who they are, but yeah, it’s cool. They’re friends and it’s actually working out.
Post-pandemic, do you feel your role as a videographer has changed?
I think it naturally has, just as everything has shifted. Yeah, there’s so much more interesting stuff to shoot out there now. I just feel so reinvigorated, just because of all the pleasure and pain around you when you’re walking around on the street now. My favorite stuff in the world, documentary-wise, captures a very specific time and place and is unashamedly just trying to give you a panoramic view of it. I’ll just go and watch those old Times Square videos of raw footage of whatever’s happening there. That’s the richest stuff to me, and that’s what I hope that the season accomplishes, too.
One more NXIVM question. Did you have to go and find one of those programs, or had you hung on to that?
Yeah, my friend who was in the a cappella group, his name was also John. He had the foresight back then to hold on to the program and the T-shirts that Keith gave us. When I decided to pull the trigger on this episode, I contacted him for the first time in a few years, and he still had it. I had him mail me the ephemera. I just shot it and then mailed it back to him. So he’s still got it.
Do the other members of the group feel the same vindication that you felt?
I don’t think they think about it as much as I do. I think they’re just like, “Well, that was weird.” But a couple of them do. My two friends whose names were also John in the a cappella group, we had a little text thread as things were beginning to come out about Allison [Mack] and everything. But yeah, it was limited to that.Want more Thrillist? Follow us on Instagram, Twitter, Pinterest, YouTube, TikTok, and Snapchat.
Esther Zuckerman is a senior entertainment writer at Thrillist. Follow her on Twitter @ezwrites.