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‘How To with John Wilson’ and Its Beautiful, Bittersweet Season Finales

Two surprisingly distinct episodes — one about a changing world and the other about how to live in it — are perfect, unexpected entry points into this HBO series' abundant charms.

How To with John Wilson Season 2 HBO

“How To with John Wilson”

Joe Buglewicz/HBO

[This post originally appeared as part of Recommendation Machine, IndieWire’s daily TV picks feature.]

Where to Watch ‘How To with John Wilson: HBO Max

“How To with John Wilson” isn’t exactly a show with twists, but there’s always more lurking behind each episode title. Improving your memory eventually becomes a consideration of what happens when people experience reality in fundamentally different ways. A crash course in wine appreciation slowly morphs into an existential look at how we treat things that linger in our lives.

There’s maybe no better example than the episode that ended the 2020 season, “How to Cook the Perfect Risotto,” still one of the pieces of entertainment that best captures the feelings of that year. It takes the simple idea of executing a recipe and does what the best “How To” episodes do: uses the entire city of New York as an ever-shifting, ever-surprising canvas. In the process, it ties together the thematic throughlines of the half-hour mini-documentaries that come before it and turns Wilson’s landlord into something of a niche breakout star in her own right.

For a Season 2 finale follow-up, the show looks to “How to Be Spontaneous” as its title guide. If Season 1 documented a city on the verge of an immense, globally resonant change, Season 2 shows the ways the city has kept a certain level of persistence, even as we’re multiple years into a worldwide health crisis. There will still be collectors and hobbyists with wildly unexpected enthusiasm. Locals will be willfully oblivious to the things in their periphery, whether they’re brightly colored oddities or the bevy of other TV shows filming on the block. And people running away from clowns will always be funny.

Overall, Season 2 has a looser feeling, with more wide-ranging topics fitting under a single episode umbrella. The first round of episodes managed to impose some order onto chaos. Maybe “Risotto” was a shift, but Season 2 seems to embrace more of that chaos, even if it’s all still presented with Wilson’s steady-voiced narration underneath. There’s always been a streak of disguised mischief in the show’s DNA. Watching Wilson crash a corporate celebration or set up shop inside a giant convention or buy a building over the course of Season 2 grows that scope wider and wider.

Despite rarely appearing on camera, Wilson has helped make “How To” an incredibly personal text. It goes beyond the sight gags of pages of detail-free entries in his dream journal or sifting through his old high school projects. While the first season stumbled on incredible conversations with random New Yorkers who each found themselves in possession of wild artifacts or at the forefront of some impulsive business venture, those Season 2 searches are aimed more and more inward. Wilson isn’t just giving his own experiences some second-person narration remove. He’s providing proof of the bizarre ways his life has collided with people at the center of major news events. (Wouldn’t dream of spoiling it here, but some a cappella recollections lead to an incredibly jarring abrupt right turn.)

Along the way, though, all the trademark visual storytelling of Season 1 is still there. In one late Season 2 episode, Wilson tells the story of a theoretical relationship entirely through vanity plates. In finding repetition out in the streets of New York, Wilson can connect the entire city with people doing simple squats or by whatever they leave out to save their parking spots. And who knows what you’ll see people doing in their car with an unusual level of straightforward confidence.

All of these swirling ideas come to a crest in “How to Be Spontaneous,” a Season 2 finale so thoroughly tapped into the anxieties of making any plans in world where personal interaction still carries a calculated risk. Writers Michael Koman, Alice Gregory, Susan Orlean, Conner O’Malley, and Wilson (who each work on multiple other episodes throughout the season) tie in failed wedding plans, flustered beach trips, the legal definition of the word “intent,” and one very funny cassette tape choice. (The B-roll for Wilson talking about meeting “the love of your life somewhere” is also a pairing that pretty much only this show would think to make.)

It builds to the particular “How To” running theme of tiny victories. Documentary projects are built on a weird, magical combination of planning and sheer good fortune. The snow happens to fall on the roof in the same shot as a pan down to a dead pigeon. A pig trots by a group of police officers. Someone writes the phrase “I will smash your windows 100%” on the wall outside their property. Sometimes you happen to be in the right place at the right time to witness something truly incredible. The beauty of “How To with John Wilson” is that it’s slowly training you to see those moments as they happen.

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