There are a few defining qualities to an episode of the comedy docuseries How to With John Wilson. Every single episode features unique and unglamorous shots of New York City and the people who live there, capturing a very real slice of life in the city. More often than not, John Wilson’s pursuit to answer a seemingly simple and broad question leads him to examining highly specific, niche groups — in the show’s final season, which wrapped on September 1, he delves into communities of vacuum cleaner enthusiasts and cryogenic supporters. Wilson’s personal life is mostly unimportant to the telling of his stories, but slowly over time he reveals more and more about himself through the lens of those he’s interacting with, making the whole series slyly personal.
While the DNA of Wilson’s series seems very particular, there’s another HBO show that checks all those same boxes: High Maintenance. The comedy anthology, created by Ben Sinclair and Katja Blichfeld, loosely follows one person’s interactions in New York City, a man simply known for most of the series as “The Guy” (Sinclair). He’s a cycling weed dealer who caters to clients in all boroughs and walks of life, and though he’s the common thread through each episode, his customers are the ones who take the spotlight. The world is shown through various perspectives, from that of a pair of obnoxious partiers or a grieving agoraphobe or, in one of the series’s best episodes, a dog. New York looks a little different to each person (or animal), and each has their own set of eccentricities to set them apart.
Like Wilson, the Guy is mostly an observer of human nature. He gets caught up in the drama every once in a while, too, but there are plenty of episodes in which his sole purpose is to tie one set of characters to another. When he is present, people feel comfortable opening up to him, sometimes revealing more than they intended, catapulting them into adventures of their own. Some of the characters are closer to the Guy than others and reappear throughout the series because of it — it’s similar to how Wilson turns his landlord into a recurring character in his docuseries, checking back in with her periodically to capture another very specific moment in her life.
It’s never quite clear where an episode of High Maintenance may go. An episode that starts with the Guy making a delivery to a new set of parents can quickly change course to follow a completely different couple who just happen to be walking by the window. Characters from past episodes may pop up in the background of someone else’s story, showing just how entangled the lives of New Yorkers can be. And when the focus is turned on the Guy, there’s almost always an unexpected and poignant detail about his past and perspective on the world waiting to be revealed.
Both series also had similar trajectories to success, starting out with videos online before landing at HBO. Wilson’s earliest “How To” videos can be found among his other experimental documentary work on his Vimeo page, while the entirety of the High Maintenance web series, which originally debuted on Vimeo in 2012, is now streaming on Max. While it’s not entirely necessary to go all the way back to the beginning to enjoy the HBO series, it adds more context and appreciation for call backs presented later in the series — for instance Patrick (Michael Cyril Creighton), who first appears in the webisode “Helen,” pops up multiple times throughout the series, with each appearance hinting at his character’s significant growth. It’s more satisfying to see where he ends up when you know exactly where he started.
The biggest, most obvious difference between the two series is that one is a documentary while the other is a scripted comedy-drama. And yet, Wilson’s exploration of some of the oddest characters in the city make the most outlandish narratives and people in High Maintenance seem more believable.
High Maintenance ended after four seasons because its creators were ready to pursue other creative endeavors. That decision at least allowed them to go out on their own terms, wrapping up the entire project’s eight-year run with a satisfying, revelatory finale focused entirely on the Guy. While Wilson didn’t necessarily turn the spotlight on himself in his series finale, he did use the episode to get more personal than ever. In both cases, the finale episodes made clear that while these particular arcs and projects were coming to a close, there’s still an entire city (and world) of characters with entertaining, heartbreaking, mystifying, and bizarre stories that are just waiting to be explored by the next Sinclair and Blichfeld or Wilson.
High Maintenance Web Series Season 1 and High Maintenance Seasons 1 through 4 are streaming on Max. Join the discussion about the show in our forums.
Brianna Wellen is a TV Reporter at Primetimer who became obsessed with television when her parents let her stay up late to watch E.R.