‘How to with John Wilson’ remains one of television’s most eccentric and personal shows

Hey, New York. 

By now, there’s a decent chance that you’ve seen—or, at least heard of—HBO’s How to with John Wilson. An eccentric, eclectic, often excellent first-person exploration of the various oddities of New York City (and beyond), all explored through deceivingly basic or banal subjects like “How to Make Small Talk” and “How to Split the Check,” to name only a couple examples, the series will disarm you with its dishonest straightforwardness. But much like the show itself, John Wilson is quick to trick with his narrative aspirations. 

Such starting points will evolve (or, perhaps, devolve) into weirder, more outlandish, more uncomfortable, and certainly more unexpectedly poignant directions over the course of an often unpredictable half-hour. And what started as, say, a guide into New York’s storied history of scaffolding will become an investigative exploration on what it means to be alive in a world that feels suffocating and liberating all at once. As a result, it’s a hard program to describe in simple terms, despite the show making it seem so … simple. Yet, it’s easily one of the best, most unique, and most humane shows on TV right now. And thankfully, this year’s second season only continues its exceptionalism. 

In Season 2, which starts with our titular documentarian exploring “How To Invest in Real Estate” and ends with a Vegas-bound “How To Be Spontaneous,” John Wilson opts to get both more personable and more personal, bringing genuine compassion to his oddball subjects while also letting his guard down and opening up in unsuspecting moments. By doing so, he reveals some previously unknown truths about his past, which continues to inform his mild-mannered interest in everyday topics and his desire to connect with people—often strangers—in casual, yet meaningful, interactions. 


A desire to learn how to appreciate wine in Episode 2, for instance, results in our curious cameraman disclosing a shocking revelation about his college acapella group. Even weeks later, I have whiplash thinking about its sinister implications. Likewise, an episode trying to figure out how to throw away batteries allows Wilson to rip a long-standing band-aid from his past, as he tries (in vain) to discuss an extremely-embarrassing first movie from his high school years: the well-intentioned, if ill-received, feel-good holiday tale, Jingle Berry

By freeing himself to be more acutely self-reflective and self-deprecating, Wilson lets down his veneer a little bit but also lets himself—and, by extension, the audience—have a more charitable perspective on the people we interact otherwise, however fleetingly, notably in such cynical and physically/emotionally distant times. While the filmmaker/essayist deliberately seeks out unconventional and often unbecoming personalities, it’s apparent that the goal isn’t simply to gawk at their imperfections and infelicities.

Rather, How to with John Wilson Season 2 proves that he’s using his admirably shabby platform to get to the root of what it means to be alive in an uncertain age, one that continues to grow more alarming, more divided, and more socially and morally alienated, and figure out the ways in which our odd, individualistic interests make us more connected—usually in the most unlikely ways.

While the charming first season was often great at establishing the documentary show’s singular tone and appealingly haphazard style, there was occasionally an uncomfortable concern as to the showrunner’s intentions. The show never seemed mean-spirited; quite the opposite, really. However, because Wilson so often remained so guarded—an unconventional television host who was constantly behind, opposed to in front of, the camera—there was the lingering question of how much of this acutely-funny docuseries was emotionally sincere. Was there a deliberate ironic distance at play? How sincere was this comedic slice-of-life exploration? 


Though it’s hard to discern where John Wilson, the director, begins, and where “John Wilson,” our ungainly, socially inept casual NYC resident, ends, it was easy to assume that this was all some weird bit of performance art. Maybe one that was meant to poke fun at random citizens caught on-camera in their day-to-day outings. Or giggling at the utter strangeness of the random personalities with incredibly atypical interests and/or professions, particularly those who were also willing to speak at length about their far out fixations.

In the internet age, it can be easy to assume the worst. To believe that people don’t have other people’s interests at heart. The Nathan Fielder-produced show did seem like a lark when it debuted. But to the show’s credit, and to the benefit of this fleshed-out new season, How To with John Wilson proves to be a delicately yearning show—even a balm in hard times—and Wilson’s command of tone (especially as his focus constant shifts) in Season 2 is truly outstanding. 

The line between befuddled bemusement and derision was walked delicately in Season 1, even when it favored X-rated sensationalism, and it was a balancing act that seemed hard to trace when entering another year—particularly as the show gained even more critical appreciation. Thankfully, while the novelty was gone, Wilson never lost his ability to surprise and impress. He relied on the show’s now-established formula to dig deeper into his sense of self as a person and artist, while at the same time allowing his unwavering focus—via his free-wielding camera—to bring more casually discerning sympathy and exploitative interest to many more unlikely subjects, including (as always) himself. 

With the surprise added benefit of writers like Connor O’Malley and Susan Orlean, How To with John Wilson’s Season 2 is more emboldened to find loosely connected talking heads, including an energy drink mogul and a young man who eats decades-old Vietnam War-era LRP rations, and more comfortable with letting Wilson’s own life story take the center stage.


Balanced so beautifully in it Season 1’s finale, “How To Cook the Perfect Risotto,” which became one of the very few defining examinations of our shifting cultural tide that resulted from the onset of the pandemic, Wilson’s new season allows the restrictions that come from our COVID-ridden times to make the human interest series more introspective and subjective, to give more introverted insight that enriches rather than detracts from its rambling thesis. 

By learning more about Wilson’s home life, notably with the filmmaker’s lovely landlord taking the central focus of the show’s season premiere, and gaining more insight into Wilson’s past failures and personal hardships, the very thin line between “documentary as objectivity” and “documentary as subjectivity” continues to grow even slimmer. While there’s a great deal that we don’t know (not yet, at least) about Wilson as a person, his willingness to be more vulnerable, to let us know more about his insecurities and fears as a person and storyteller, allows his always individualistic show to feel like a miracle on such a major network. 

Where else are we going to see a show that lets us grapple with the host’s inability to remember his own dreams and dig into the nature of dreams itself? Likewise, where else on television would we get an opportunity to spend time with a group of Avatar-loving super-fans, exploring their own humility in a way that never feels scornful? To spend several minutes hearing about how the imaginarium that is Pandora helps them grapple with their own mental health? Even as the scope of How to with John Wilson grows, the focus remains even more intuitive—a balance that’s difficult to achieve, yet feels effortless under Wilson’s guise. 

2020 and, subsequently, 2021, were alienating in such uniquely unsettling ways. There’s an aching sense of dysfunction, as we all struggle with how to connect to one another at a time where it can feel taboo to be in the same room with another human being. Even spending time with your family can feel wrong, somehow. It’s hard to grasp the ways in which our times will shape our minds and our general perception of reality moving forward. It’s hard to grasp what it means to be alive right now.


Through Wilson’s ever-perceptive show, there’s something so unmistakably present about the whole thing. While it wasn’t intentional, it’s hard not to envy the timing. With Season 1 coming together during the divide between 2019 and 2020, it’s the rare show to capture the shift in our landscape, the pinpoint where everything took such a radical turn. 

Likewise, at a time when it’s becoming harder to be certain about the future and make sense of our connections to others, Wilson’s curious lens is not only entertaining and inviting but a blissful, even unexpectedly meaningful reminder of our intimately human desire to understand others through ourselves. By allowing his show to become more introspective, to give us a better grasp on the man who directs the show, the evolving series becomes even more connected to its growing viewers. It’s not accidental that the series often gives us a first-person perspective, referring to Wilson’s own experiences as “you,” as though the world we live in is becoming some sort of virtual reality right now.


It’s a curious mix for a curious show that continues to discover enriching and involving ways to get us to process the ever-changing world around us, and it’s a rare blessing to watch a show that is both so uncomfortably comfortable in itself while also being so willing to push its boundaries in such meaningful and reflective ways. It showcases a series that understands what it means to be a human right now, even if it can’t quite articulate what exactly it means to be in this moment.

Presently, How To with John Wilson isn’t renewed for a third season. Not yet, at least. With all the adoration that it continues to receive, from critics and audiences alike, one hopes that HBO continues funding such a budgetarily-inexpensive-yet-narratively-rich series. With Season 2, it’s apparent that Wilson only continues to grow as a filmmaker and storyteller, allowing the once unseen layers of this new program to grow in such dynamic and distinctive ways, thus resulting in what continuously remains one of the most compellingly anomalous programs of the new decade. 

It’s so rare to see such an idiosyncratic series, one that feels so uniquely tied to its storyteller yet has a universal appeal that’s hard to ignore. But that’s ultimately the magic of How To with John Wilson, especially with Season 2. It’s undeniably one of the best, most brazen, most impressive, most impactful shows on TV today. Hell, maybe it’s even the best one. At the very least, it’s the one that seems most content with trying to figure out our present times. And we’re certainly better for having it.

I’m Will Ashton. Thanks for reading. 


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