Green, Green Grass of Home

The small-town pleasures of Brooklyn-based Web series High Maintenance.

Ben Sinclair in High Maintenance.

Video still via Janky Clown Productions

New episodes of High Maintenance, the precise and perfect Web series about affluent New York City stoners, arrive today and immediately grant entry to the best small town in serialized fiction: the one in Brooklyn linked together by the affable weed dealer known only as The Guy. The series, which is now up to 16 episodes, ranging from six to 15 minutes, is created, directed, and written by husband-and-wife duo Ben Sinclair and Katja Blichfeld. (The newest episodes are the first funded by Vimeo—and the first that aren’t available for free: They’re $2 each, “or $8 for a set that includes three more that will be released in January.”) Sinclair stars as the drug-dispensing deliveryman and each episode focuses on a different one of his customers, who, altogether, make for High Maintenance’s ever-growing cast of hyper-specific New Yorkers.

In some other era, The Guy would have been the milkman, the postman, the handy man, or some other deliverer of benign, essential services. Sinclair is tall and rangy, with a receding hairline, and until he opens his mouth he has a slightly menacing look that would probably serve a drug dealer well. (According to his IMDB credits, he has previously played such characters as “Wild Eyed Guy,” “Brooklyn Idiot,” and “Homeless Guy.” No wonder he wanted to create his own project.) But as with so many characters on High Maintenance, appearances are deceiving, and The Guy is warm and observant, with the comforting, non-judgmental vibe that turns so many of his customers into regulars.

Those regulars are distinctive and hilarious. High Maintenance may be a show about dedicated stoners, but it does not have a stoner aesthetic. It is sharp and quick and so coolly observant that it can become satirical, as when a B.S.-spewing home chef whips up some bacon-infused matzo balls for a farm-to-table Seder. Sinclair and Blichfeld have amazing ears for the absurdities of personality in general and bourgeois Brooklyn in particular. Each episode opens with a skewering and often very funny oh-god-I-think-I-know-that-person character-establishing sequence that with startling economy creates such specific archetypes as the lonely shut-in caring for his ill mother and the cross-dressing stay-at-home dad. 

The show’s New York City is populated by people who are a little bit more complicated than they seem and inspired by motives that are too unique to immediately clock. The sexy hipster chick who wants her new boyfriend to pay for everything is actually homeless. The heinous, bitchy narcissist who steals from The Guy was molested as a kid. The cross-dressing, stay-at-home dad isn’t hiding his cross-dressing from his wife—he’s hiding his weed-smoking. The seemingly shy, gym-obsessed man actually believes in aliens and is trying to become an ubermensch. These people are all types, and then a bit more.

Web series have for years now been heralded as a sort of format of the future: a way for anyone with a camera and a good idea to make a show everyone can see. But High Maintenance is one of the few that makes the case for what a Web series can do that a standard TV series cannot. One of the ironies of High Maintenance is that it uses an unusually short format—delivered in batches of just three—to build uncommon depth. If the show were airing on standard television, each episode would be required to run between 22 and 30 minutes and to deliver something a little more formulaic, with more of The Guy in each episode and a more consistent supporting cast, all in the interest of creating familiarity. Freed from those requirements, High Maintenance has episode-opening sketches that do in minutes what most sitcoms can’t do in hours: make guest stars full-bodied, familiar, funny, and heartbreaking.

Also because it is a Web series, High Maintenance does not have to worry about appealing to a huge audience (though it has probably accrued a sizeable one at this point). In the new episodes, there are some very funny lines that just wouldn’t exist in a project concerned about having the widest possible appeal. At a Fort Greene barbecue, a man complains in perfectly condescending, contrarian, party banter-style that he just can’t understand what people like about Scandal. A heated conversation between a deaf couple about Yale drama school auditions includes the line, “I thought doing the fat girl speech from Louie for my audition was such a good idea!” And lest you get the impression that High Maintenance is a bunch of knowing, pop-culture-specific jokes, the best gag in the new batch of episodes involves, yes, organic milk, but also a penis. It is the dick joke our foodie culture deserves.

In the new trio of episodes the characters orbiting loosely around The Guy pull closer together. Characters like homeless Heidi and an asexual magician have recurred before, but in the new season these connections escalate. The couple at that Fort Greene barbecue are served burgers by the wannabe ubermensch, who seems to have chilled out at a little bit (but still manages to make the male half of the couple obsessed with surviving the apocalypse). That same asexual magician, who also attended that aforementioned bacon-infused Seder, gets an entire episode about trying—and failing—to teach at a Brooklyn Public School. (Don’t do magic for high school students. They will eat you alive.)

In the last new episode, The Guy sets up two of his clients on a date. Ellen, who appeared in the episode “Brad Pitts” as a woman who had just received a cancer diagnosis, shows up again, healthier, and goes out with Victor, a doorman who also works as the guy who gets beat up in self-defense classes. High Maintenance tends to skewer hardest those characters who talk most. Ellen was always pretty quiet, and though Victor is chattier, the episode isn’t—as it with the Fort Greene survivalists—teasing. Ellen and Victor go on a date, get stoned, get awkward, and then have an uproarious incident with organic milk. By the end, two strangers have started to make a connection, which is what High Maintenance thinks New York City is all about: a place populated by strangers you just might know if you look closely enough.