If High Maintenance, the glorious web series turned HBO show about a weed dealer and his petit-bourgeois clientele, were a person, I would hide from it at a party. For a show about stoners, High Maintenance is terrifyingly sober: It sees too much; it understands too much; it is exactly as sympathetic as you deserve, which is never as sympathetic as you would like. If you were to spend any time with it while inebriated, you would surely spend the morning after drafting apologetic text messages for last night’s gauche behavior that you were too anxious to actually send. Thankfully, High Maintenance is not a person. Make a mental note to avoid its creators Ben Sinclair and Katja Blichfeld in anything but perfect form, and take pleasure in watching it pounce on allegedly fictional New Yorkers through the safety of a screen.
Depending on how you watch/borrow/steal HBO, that screen may have recently changed. High Maintenance was previously a 19-episode web series, hosted on Vimeo, consisting of gorgeously composed character sketches running anywhere from four to 12 minutes. Linked by The Guy (Sinclair), a menacing-looking but sweet-natured drug dealer, the High Maintenance web series delved with impressive economy into the lives and personalities of various residents of the small village known as New York City. The Guy works only on referrals, which makes him a dealer to a cohort of affluent, artsy, largely white residents of Brooklyn, Manhattan, and ever so occasionally Queens, many of whom appeared in multiple episodes, popping up on Guy’s daily rounds and in the lives of other clients. The drug dealer, a canny entrée into the life of strangers, is also a canny entrée into a world of acquaintances who can all play a rousing version of the name game.
As a web series, High Maintenance left nothing to be desired. Incisive, poignant, hilarious, beautiful, and perfectly scathing about Brooklyn mores, it was also extremely short. Perhaps I admire this quality because my attention span is a tattered shroud, or perhaps it is because few other TV-makers choose to be concise: The plague of hourlong shows running 15 minutes over is real. Either way, one can binge-watch all of High Maintenance in an afternoon and still have time to get outside while the sun is out, which as far as TV goes, makes it positively healthy, another chit in the weed-is-good-for-you column. High Maintenance never sacrificed depth with its brevity, perhaps because it had no plot requirements besides those of establishing character: On any given episode of High Maintenance, the only thing that needs to happen is that you get to know someone very well. And in its structural variability—not a half hour, not an hour—it was the realization of a long-promised but never-arrived moment when TV could be just as long, or short, as it needed to be.
High Maintenance was so good, no one could blame HBO for scooping it up. I did consider blaming HBO for turning it into a half-hour series, but the results are too good to quibble with. High Maintenance is impressively unruffled by its lengthened format or its move to HBO. With the exception of the episode that is told entirely from the perspective of a dog, each episode is split into two vignettes, often featuring characters from the web series. In the first episode, for example, Guy sells to an odd and menacing tough guy with a noted resemblance to Vin Diesel, and then the episode turns to Max (Max Jenkins), who appeared in the web series as a heinous gay, here making some tragicomic attempts at maturation.
The new six-episode season is so much a continuation of what came before, it may even put brand new viewers—or ones for whom La Croix, Elena Ferrante, Marie Kondo, and Hamilton are not legible social signifiers—at a slight disadvantage. Recurring characters recur again and again. An agoraphobe (Michael Cyril Creighton) caring for his dying mother who appeared in the web series reappears, his mother now dead, but his love for Helen Hunt and crush on The Guy going strong. Homeless Heidi (Greta Lee)—a con-artist who lives off her unsuspecting boyfriends—reappears, but one of her exes has now turned her exploits into a TV show. That show is itself a spoof on High Maintenance, with Brett Gelman playing The Guy.
Sinclair and Blichfeld have used the additional length and budget to be more ambitious, to explore characters outside of Guy’s usual bubble. One episode begins by exploring the life of a Pakistani American college student (Shazi Raja), a relatively good Muslim girl in the midst of a minor rebellion. Another episode moves from a Brooklyn brownstone into the life of a Chinese man (Clem Cheung) who collects cans with his wife, though he needn’t: His son is an acclaimed musician in Berlin. Having graduated to HBO, High Maintenance is more aware of its lack of diversity. A client interviews The Guy and peppers him with questions about the racial dynamic of his clientele: Does he mostly deal to white people? Does he think this is why he’s never been arrested? The Guy doesn’t handle these questions well, but their inclusion is a signal that Sinclair and Blichfeld know they are now on a bigger stage, before a bigger audience. An acknowledgement of a lack of diversity is less preferable than diversity, but better than no acknowledgement at all.
The woman asking Guy these questions is a social-media obsessive so familiar, I wondered if she was based on a person I know, until I realized that she is a type almost everyone knows. This is High Maintenance’s knack: creating specific characters who are unique and yet familiar. No one is ever exactly as they seem, whether because they are harboring a secret, or because even the most knowable type, in some quiet moment, is too human to be entirely predictable.