Weed Dealer as Caretaker: New ‘High Maintenance’ Episodes Reveal Who “The Guy” Really Is


High Maintenance released a new crop of episodes yesterday; depending on how you count them, they’re the web series’ sixth “cycle,” or third season, or the second half of its second season. They are also, predictably, excellent. In The Guy (Ben Sinclair), the series’ weed-dealing protagonist, Sinclair and co-creator Katja Blichfeld have hit on an endlessly elastic premise. With the exception of The Guy and his merchandise, there are no constants in High Maintenance, a fact that the latest season/cycle exploits to its fullest.

Combined with the three episodes released in November (“Ruth,” “Geiger,” and “Genghis”), yesterday’s crop (“Sufjan,” “Esme,” and “Sabrina”) are the results of Sinclair and Blichfeld’s partnership with Vimeo, the site’s first venture into Netflix-style original programming. Because Vimeo doesn’t have a subscription service, the episodes are available for $8 on demand; those reluctant to spend two cappuccinos sight unseen can sample the goods by watching the first 12 episodes, made sans tech money, for free.

The first 12 episodes of High Maintenance were short, nearly no-budget affairs; “Stevie,” the premiere, is an encounter between The Guy and a high-strung assistant that plays out over just five minutes, never leaving the assistant’s hotel room. Vimeo financing subsequently allowed Blichfeld and Sinclair, who also happen to be married, to go longer and more ambitious. For the first crop of Vimeo episodes, that ambition took the form of making High Maintenance into more of a self-contained world.

While the majority of early installments were standalone glimpses into the lives of characters we’d never see again, each of the November episodes featured plots driven by, if not starring, familiar faces. “Ruth” picks up the story of the cancer patient from “Brad Pitts” after the death of her namesake older friend; “Genghis” follows Evan, the asexual magician from “Elijah,” as he tries out teaching in a Brooklyn public school; “Geiger” sees a couple implode after the cult member from “Qasim” gets a woman’s fiancé hooked on survivalism. High Maintenance had experimented with continuity before: “Matilda,” an episode where The Guy’s middle school-aged niece comes to visit from Arizona, is practically a greatest-hits roster of past characters, like the mouse-hating lesbian couple who host a knockoff TED event in their loft. Still, the initial Vimeo episodes gathered a scattered constellation of characters closer together than ever.

The second crop of Vimeo episodes have their share of recurring characters and in-jokes. Evan pops up once again to introduce The Guy to some new clients in “Sufjan,” and we finally meet the namesake character from “Dinah.” But each new episode is also a departure from form, if an anthology show with just 15 installments can be said to have a form. “Sufjan” takes us away from the typical hipster haunts of Williamsburg, Bushwick, and Crown Heights to Ditmas Park, the tree-lined neighborhood that’s Sinclair and Blichfeld’s home IRL (and also the pseudo-Iowa from this season of Girls). “Esme” reminds us that The Guy isn’t the only dealer on the scene, giving us a deliverywoman who’s as cartoonishly awful as The Guy is empathetic and unfazed. And “Sabrina” crosses the biggest line of all, breaking off High Maintenance‘s symbiotic relationship with New York for a weekend at a country house.

Of course, High Maintenance remains committed to being the most particularly New York show on not-quite-TV. “Sufjan” is, after all, a real estate episode, a crucial rite of passage in any effort to capture what it’s like to live in a city where being able to fit 20 people in your living room is a cause for celebration (see Broad City‘s “Apartment Hunters” or Hannah Horvath’s astonishment at what $250 a month can get you in the Midwest). A couple’s struggles with outer-Brooklyn yoga studios and friends who won’t visit once they look up Ditmas Park on Hopstop are just the beginning; The Guy also helps out a family of Orthodox Jews in need of a Shabbos goy and takes part in the most New York pastime of all: ragging on LA.

More than New York, however, The Guy remains the heart of the show, a carefully neutral eye in a hurricane of yuppie neuroses. The more clients change — sad-sack doctor Kabir from “Dinah” dumped his girlfriend and now takes classes at UCB; Orange Is the New Black‘s Yael Stone plays a buyer who’s defected for Esme’s all-womyn weed collective, albeit temporarily — the more Sinclair’s good-natured Guy stays the same. Nothing emphasizes this quite like “Sabrina,” the longest and best of the new episodes. At the country house, The Guy is on vacation, just like everybody else, but still finds time to coach a struggling entertainer through a pill-addled career crisis. Even when he’s not selling weed, the activity that’s supposedly the premise for the whole show, he still finds a way to help someone out.

It’s a scene that makes explicit what High Maintenance has implied all along. The Guy, with all his easygoing charm, isn’t just — or even primarily — a supplier. He’s a caretaker, complete with bedside manner. And with all their apartment woes and struggling podcasts and failed Stomp auditions, a caretaker is just what his clients need.