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How ‘High Maintenance’ captures the challenges of finding community in the city

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The Guy’s weed deliveries feature a parade of New Yorkers seeking calm and community

High Maintenance’s main character, the weed deliveryman Guy, being greeted by a customer.
On its surface, the travails of the Guy (played by High Maintenance co-creator Ben Sinclair) is simply a comedy of errors about that particular urban fixture, the affable weed delivery guy, cycling between customers with comedy ensuing at every stop.
HBO

Like, what’s it all about, man? While pondering the deeper meaning of High Maintenance, the web series-turned-HBO-darling about a bearded weed deliveryman, it’s hard not to imagine someone pacing inside a four-story Brooklyn walk-up, gulping from a vape pen and asking the big questions.

On its surface, the travails of the Guy (played by High Maintenance co-creator Ben Sinclair) is simply a comedy of errors about that particular urban fixture, the affable weed delivery guy, cycling between customers with comedy ensuing at every stop. Go a little deeper, however, and it’s clear the series, which was renewed for another season this spring, is about the city, an endless series of character studies that finds a narrative thread via everybody’s desire for a little calm and community in a chaotic cityscape.

“We were really interested in creating the most New York world possible,” production designer Almitra Corey previously told Curbed.

High Maintenance does an excellent job of getting out of Williamsburg and Lower Manhattan, getting past the fantasies of affordable and easily accessible city living found in previous Manhattan-centric shows like Sex and the City and Friends, as well as seeing the diverse lives that make up a true 21st-century metropolis. From scenes in Astoria and Crown Heights to an amusing storyline about Ditmas Park⁠—a couple finds they are losing touch with their friends and former life living so far away from the center of Brooklyn⁠—it’s filled with New York stories and characters that rarely get the camera’s undivided attention.

While the parade of diverse smokers—and intimate entree into their apartments and inner lives—has made the show perhaps the realest distillation of New York City life circa 2019, it also shows the fleeting nature of community in the city, and the sorry state of our shared spaces. Today’s painful real estate realities, like being forced to place that spare room on Airbnb (and deal with the resulting influx of hard-partying European tourists), or watching your neighborhood gentrify from the stoop of your apartment building, constantly play out in the background of Guy’s delivery route.

Guy’s trips take him between boroughs and up and down the income brackets that divide the city (not too low—remember, these people do pay for weed delivery). He sees many of the same forces playing out across the city: rapid change, rising rents, and a shared feeling of displacement, disorientation, or a loss of connection.

“I think that because of technology and how capitalism has really caught on in the world, I think we’re all just thinking that we are an island, and I think human beings are meant to be together,” Sinclair told NPR while talking about the show.

If you’re already feeling disconnected, and aren’t sure who to reach out to, where does one go in the city? In the first season alone, one customer, whose primary job appears to be taking care of his ill mother, seems to call the Guy simply for company, while guest star Hannibal Buress, in a later episode, breaks down in the Guy’s company after a shooting during his set at a comedy club.

Consider other sitcoms or TV shows formatted around a protagonist interacting with new characters every week. The bar in Cheers was the paragon of a third place, as was Sesame Street for those well under the drinking age. Even Taxi returned to the same garage every episode. In High Maintenance, many of the real connections are made in the city’s most democratic third places⁠—subways cars⁠ and sidewalks⁠. The occasional moments of serendipity and community—the feminist speaking event Guy ends up taking his niece to after failing to land Broadway tickets—only reinforce the magic, and rarity, of such interactions.

I tend to look at the show as a sad reminder of things that, as New York continues to evolve, it’s rapidly shedding: quality public space and the kind of accessible third places that bring everyone together. As Sinclair said during an interview earlier this year with co-creator Katja Blichfeld, it’s really about the way that inviting a weed dealer into your house allows viewers to instantly pick up character info on the walls and see “an anxiety, a neurosis, a loneliness.” It’s not about the pot, man. It’s about one man’s long trek though the city, looking for connection.