📞 Secret World No.6: How to write a newsletter

There’s a genre of video I think about a lot. The best example of it might be this 1993 HD television test footage. Or 2:30am at a 7-11 near Disney World in 1987. The writer Jamie Lauren Keiles once referred to these videos on Twitter as “bygone subcultural type walking around old new york with camcorder.” I first mentioned this a few newsletters ago, under different circumstances. But I mention it again because I think it’s key to what makes HBO’s How To with John Wilson so good.

The premise of the show is deceivingly simple. Documentary filmmaker John Wilson takes us around New York City and embarks on small missions of self-discovery. Episodes cover How To Make Small Talk, How To Improve Your Memory, and How To Make the Perfect Risotto. But these are not the slickly-produced how-to videos you might find on YouTube (it’s not until the last episode, How To Make Risotto, that Wilson finally skewers the genre). Rather, How To follows in the footsteps of shows like The Simpsons, where what seems like a simple, straightforward journey at the outset of each episode takes us into unexpected, delightful, frequently uncomfortable (and uncomfortably funny) directions. Wilson’s quest to prevent his cat from scratching his couch turns into a sober examination of defensive architecture and, uh, circumcision. An attempt to memorize a grocery list — featuring one of the show’s best sequences of visual gags — leads Wilson to conspiracy theorists and believers in the Mandela Effect. After Wilson tries to figure out the best way to split a restaurant bill, he’s lectured on income inequality by the owner of a neon sign shop, and ends up at a dinner for soccer referees in Long Island. But Wilson always, somehow, circles back to the initial premise, and in the process learns something about himself.

If that all sounds a bit too earnest, well, it is! But that endearing earnestness is one of the show’s greatest strengths. Each episode is quite literally told from Wilson’s perspective; other than the most fleeting mirrored glimpses, you almost never see Wilson on-screen. He remains behind the camera — and often to comedic effect, like when Wilson is reduced to opening a can of soda or cooking with his other free hand. He narrates, not necessarily what we see, but what he sees. We get to experience the world and all its mundane wonders through Wilson’s eyes. In fact, so many of the show’s best, funniest, most endearing moments hinge on how it’s shot — the slow, faceless, meandering magic of the early days of home video mixed with the virality, humour, and personality of the videos we upload to the internet today.

The slices of city life that Wilson captures feel like the sort of context-less shots you might see on TikTok, Instagram, on Twitter — short, weird, engrossing, unexpected, and often annotated with some witty remark or wordplay for comedic effect. A giant teddy bear lying forlornly on a sidewalk. A restaurant with a name that evokes Wilson’s mood. Pillows on a hotel bathroom floor. Paired with his anxious, and uncomfortable narration, the show is rife with visual gags — perfect, unexpected juxtapositions that can take a beat for the joke to land. It’s never quite clear what will happen next, or where everything is leading, to the point where I found the show’s pacing unsettling, almost frustrating, at first. But like any good how-to, you have to trust the process. You can’t skip steps. And you’re rewarded for your patience. Thanks to Wilson, I’ve been thinking about scaffolding all week.

The show is a love letter to New York City’s specific strain of weirdness, yes, but it’s also a reminder of city life at its best — of the things you see when you stop, slow down, look around. It evokes the feeling of aimless wandering, of the weekend stroll. You notice shops and people you never noticed before. You soak it all in. No one films video of this anymore! And if we do, it’s probably because you, a friend, or a loved one is in the shot. But the footage in How To often feels like it was shot in an era when cameras were still a novelty. People didn’t film with as much purpose, because the purpose was to film. And what you got was faceless, unremarkable. Boring, even. Test footage of funny restaurant signs. People going about their day. But in the ordinary of the everyday is where Wilson finds his magic.

The vibe of the show makes a lot more sense once you realize that comedian Nathan Fielder is an executive producer. But where Fielder’s own show Nathan For You forced its uncomfortable host onto unsuspecting marks, How To does the opposite. Often, it’s Wilson who has no idea what to do with the people he meets — people who talk calmly, openly, about deeply personal things, who willingly volunteer intimate details about their lives. Wilson rarely fills the inevitable silences, which only compels his subjects to talk more. In those moments of escalation, you will laugh and you will squirm. “How to cover furniture” captures this feeling at its peak. I won’t spoil it for you, if you haven’t already seen it, other than to quote Wilson: “I had never met a more passionate advocate for keeping a cover on.”

Even though he stays behind the camera, Wilson slowly opens up to us, too. We learn bits about his life. We see glimpses of his apartment. But although Wilson is a part of each episode, he never lingers on himself for long, preferring to turn the camera on others — until the series’ end when the arrival of the pandemic suddenly derails his efforts at self-improvement. I don’t leave my neighbourhood much these days. I haven’t been downtown in months. At times, it’s easy to forget why I live here, or what’s waiting on the other side. But as Wilson learns in isolation to make risotto for his elderly landlord — a gesture of thanks for all she’s done for him — it becomes obvious why so many of us continue to choose city life. Cities are full of weird, wonderful people, and people can teach us a lot.

Secret World is a newsletter from writer Matthew Braga. It’s been on a bit of a hiatus. If you’re not familiar with me or my work, be sure to check out my website, and consider following me on Twitter.