Early in the first episode of How To with John Wilson, “How To Invest in Real Estate,” Wilson tries to explain what exactly his show is. “I’m a documentarian. It’s kind of like memoir, essay…it takes place in New York.” As Wilson struggles to describe his own series, the person he’s talking to clearly regrets asking about Wilson’s show. To be fair, How To with John Wilson is a hard show to explain to the uninitiated. Wilson explores what seems like a simple concept, expands it into something much bigger than the audience could ever expect, all while utilizing strange footage Wilson has captured in his home of New York City. But most importantly, How To with John Wilson is one of the most inventive, brilliant, and hilarious shows of television, and Season 2 continues the show’s greatness with an added personal touch.
The first season of How To with John Wilson felt more like a story about New York City, about what makes the city so extraordinary, all while presenting Wilson’s incredible videos. However, last season’s final episode, “How To Cook the Perfect Risotto,” told a more personal story about how COVID had affected the city he loves, himself and his landlord, with whom he has a very close relationship. “How To Cook the Perfect Risotto” wasn’t just one of the best pieces of entertainment about the pandemic, but was easily one of the best episodes of television last year.
Season 2 has taken a hint from the success of “How To Cook the Perfect Risotto,” as this season feels far more personal than the previous one. How To doesn’t break the formula that works, but we do learn more about who Wilson is. We spend a bit more time with his landlord, we get to see his friends and girlfriend, and we learn about his past in shady a cappella competitions, and a Christmas film Jingle Berry that he made in high school. These moments are spare, but they do help us further understand Wilson in lovely ways. In Season 1, we saw the city through the eyes of Wilson, but in Season 2, we start to learn even more about the person behind the camera.
Even the topics that Wilson tackles in Season 2 seem a bit weightier. In “How To Invest in Real Estate,” Wilson investigates his own problems with commitment, explores becoming a landlord, and talks about his past living in a dumpy warehouse whose exterior was used to represent Syria on an episode of Madam Secretary. The six episodes of Season 2 continue to explore the city, but by becoming even more introspective, How To with John Wilson often feels richer than Season 1.
The reason for this might be the show’s two new writers. In addition to Wilson, Michael Koman (Nathan For You), and Alice Gregory, How To has added “The Orchid Thief” writer Susan Orlean and Conner O’Malley (Late Night with Seth Meyers). While O’Malley is probably best known for his absurd and manic videos online, his work on Joe Pera Talks with You and the show’s ability to expand beyond an episode’s simple concept makes him an excellent addition. Similarly, Orlean’s books, with their careful attention to detail, also make her a surprising, yet perfect choice to write for Wilson’s show. In a way, this season is almost a composite of two of the best comedies of the 2010s: Joe Pera Talks with You’s quiet observations about the world around him, and the ludicrous yet real situations of Nathan For You, which makes sense since Nathan Fielder is also an executive producer on How To.
But the key to How To with John Wilson’s greatness is the way it can completely surprise the viewer. In one of the later episodes, Wilson visits a fan club for a surprisingly popular movie. At first, the setup is so ridiculous, it’s hard not to laugh at the people in the group. Yet as Wilson spends more time with them, we start to see how this group almost works like therapy for these people, that they’ve found an uplifting and supportive community. In the end, Wilson’s experience with these people becomes a surprisingly emotional experience, a lovely moment that comes out of seemingly nowhere.
How to With John Wilson frequently offers up these types of surprising experiences, whether it’s how each scene we are watching syncs up to Wilson’s script, or how Wilson will shift an episode to a moving exploration of death or mental health. There’s no telling what will come next in Wilson’s New York memoir/essay exploration. It’s a thrilling experiment to watch unfold, full of unusual characters and moments, and Wilson’s ingenious commentary. Even the way Wilson says “wow” in his various exploits is hysterical.
How To with John Wilson’s second season continues the series’ trend of being one of the most original, profound, and continuously entertaining comedies in recent memory. There is nothing like How To with John Wilson, and now that we know more about the man whose eyes we are seeing the world through, Wilson’s show is only getting better. How To with John Wilson is an absolute gem, an exhilarating and side-splitting series that could even change the way you look at the world.
How To with John Wilson Season 2 premieres on HBO on November 26, with new episodes airing on Fridays. How To with John Wilson is also available on HBO Max.