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HBO’s Most Soulful Show Is About a Weed Dealer

The Guy cycling down a NYC street.

In a time of remakes, revamps, and remasters, I’ve been finding myself seeking old favorites just for the thrill of experiencing an original concept through older eyes. By far, the best experience from this retreading was rediscovering High Maintenance—and discovering that, despite its relatively simple premise, it’s still one of the most soulful shows I’ve ever seen.

High Maintenance follows the daily lives of everyone in NYC who’s ever crossed paths with The Guy: a bearded, bicycling weed dealer whose voice could put a raging bear to sleep. The structure of the show is like a series of vignettes, showcasing the lives of a wide variety of people, with The Guy making appearances of varying longevity on a case-by-case basis. It originally began as a web series (which has only recently been added to HBO Max!) before arranging a deal with HBO in 2016. In total, there are six seasons of short webisodes, and four seasons of TV episodes.

You’d think that a show whose premise is rooted in weed culture in the 2010s would be kind of superfluous, but the tone of the show is almost monastic in how it portrays its subjects. There’s never a sense of judgment for people we’re typically “conditioned” to judge on TV; at most, the show will poke at absurd situations, but never take it to a cruel, dehumanizing degree.

For instance, one recurring character is an older gay man who lives with his sick mother, spending most of his time watching TV with her. When she passes, he becomes intensely agoraphobic, ordering cases of his favorite LaCroix flavor and making art out of trash as a way of passing the time. He’s lonely and leads an almost entirely solitary life as he mourns his mother, but whereas most shows would either sensationalize his pain or mock him for it, High Maintenance makes you feel intense empathy for him. You root for him as he finally steps outside, and you don’t judge him for whatever little blunders he makes. When he finally allows himself to grieve, in the arms of a motherly trans woman who helps him come down from an anxiety attack, you really feel his catharsis in that moment.

The show transcends racial barriers, too, which is pretty impressive considering its network contemporary was the incredibly white Girls (also in NYC). We get glimpses into all kinds of families and lives within The Guy’s network, from a Desi college student who lives with her parents and has to hide her clubbing lifestyle to a Gaysian couple who lead a very, very kinky day-to-day lifestyle. You really get the sense that show creators Ben Sinclair (who also plays The Guy) and Katja Blichfeld know their city to a profoundly intimate degree, and therefore they want to give all sides of it a proper examination.

The Guy’s own personal journey is also something I find fun to follow. Yes, most of the time he’s the voice of reason with a comedic bent to him, but he’s also got struggles of his own that are taken seriously. He enjoys doing things on his own, yet he’s unafraid of forming genuine connections with everyone he meets; many of his clients end up becoming friends, such as the delightful recurring character Evan, an asexual, cartoon-loving magician.

Of course, this also leaves him vulnerable to heartbreak and pain, as his nonjudgmental way of living doesn’t always protect him from other peoples’ BS. What’s admirable about The Guy is he doesn’t let his negative experiences distract him from why he loves what he does. He still goes out in the world and leaves himself open to all the weird, wonderful things that could happen in an average NYC day.

I could really just go on and on about everything I’ve loved in this show, from its portrayals of healthy solitude and transcendent, sometimes strange bonds, to its fantastic sense of humor. Few shows have made me feel so much love for the world and for the self as this one has. I mean, damn, I don’t even like visiting NYC, yet every time I watch High Maintenance, I find myself looking up things to do there.

So, if you’re looking for something that will make you feel a little bit better about being yourself, or if you’re just a fan of stories that are character-centric, you absolutely must give High Maintenance a shot. I guarantee you, you will walk away from it viewing strangers in your everyday life a little bit differently.

(featured image: HBO)

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Madeline (she/her) is a staff writer with a focus on AANHPI and mixed-race representation. She enjoys covering a wide variety of topics, but her primary beats are music and gaming. Her journey into digital media began in college, primarily regarding audio: in 2018, she started producing her own music, which helped her secure a radio show and co-produce a local history podcast through 2019 and 2020. After graduating from UC Santa Cruz summa cum laude, her focus shifted to digital writing, where she's happy to say her History degree has certainly come in handy! When she's not working, she enjoys taking long walks, playing the guitar, and writing her own little stories (which may or may not ever see the light of day).