In a newly recorded introduction to the web episode “Rachel,” Sinclair describes the duo’s “attitude” toward making High Maintenance: “We want to have a non-judgmental outlook and treat pot-smoking and any other behavior that has formerly been demonized as part of our lives and part of the life.” It’s a risibly noble aim for such a charmingly modest project, but more often than not, High Maintenance achieves its Humans Of New York Who Smoke Pot aspirations. Sculpting characters where other shows might churn out caricatures, the show practices a behind-closed-doors compassion that extends even to its riff on the boogeywoman of late-’00s Brooklyn: The Hipster Grifter. (In a meta-interlude from the show’s first season on HBO, that character, played by Greta Lee, pursues legal action against the mark who’s turned her story into a sitcom pilot—complete with Brett Gelman as an ersatz Guy.) The Guy only conducts business in private, and that gives the show a built-in intimacy, its slices of life and awkward encounters set in the cramped confines of some walk-up or another.
With more elbow room in the areas of runtime and production value, the HBO episodes function as sequels of sorts to High Maintenance’s online run. Figures from the show’s past are revisited and redeemed, their stories inevitably interwoven with new faces on the client list. The high-strung assistant from “Stevie” (Bridget Moloney) resurfaces with her father—who’s reinventing himself post-retirement—in tow; a depressive pet owner who moves to the big city winds up using the dog-walking services of The Guy’s mushroom-hawking lady friend (Yael Stone). In addition to offering a welcome nod of recognition toward the fans, the decision to continue stories from the webseries uncovers poignancy in unexpected places, like the segment from the premiere that catches up with the proto-Difficult People played by Heléne Yorke and Max Jenkins.
The commitment to recurring characters could prove alienating to viewers who aren’t operating with the complete dossier on, say, the cross-dressing writer Dan Stevens plays in the second HBO episode, “Museebat.” (Presumably anticipating this, HBO has uploaded all previous High Maintenance episodes to its streaming platforms.) But the show does its level best to mitigate these concerns, dividing its time between established denizens of this world and the premium-cable newcomers, the episodes split into halves of Vimeo-ready proportions. The mix of old and new works in the High Maintenance’s favor, if only for the sake of verisimilitude. The Guy makes it a policy only to sell to people he knows and people they can vouch for, so he ought to be retracing his steps and crossing paths with the same folks time and again. It’s a clever step for world-building, one that establishes a human-sized scale for stories set in a city of 8.5 million.
At the center of it all is Sinclair, whose embodiment of The Guy has grown increasingly comfortable and less squirrely over the years. The HBO version of High Maintenance goes much longer without appearances from its ostensible protagonist, which only makes the heart grow fonder for this wide-eyed observer existing on the fringes of mainstream society. He can use the camera’s sympathy as much as anyone on this show: His line of work is still illegal, after all, and as the worried glances of strangers and the shouts of motorists remind us, The Guy is in the same “demonized” lane as his customers.
At the risk of sacrificing some of their main character’s mystique, Sinclair and Blichfeld delve deeper into The Guy’s life in these half-hour episodes, one of the smaller tweaks to their established formula. Elsewhere, they experiment more boldly with Time Warner’s money, going for a network-single-cam tone during the episode with Lee’s character, or telling a story from a dog’s eye view. (More than any other episode, the latter seems like an appeal to draw stoners with cable away from Adult Swim and back to the night and channel where they used to congregate for Mr. Show With Bob And David.) Despite his delivery route’s familiarity, The Guy still has plenty of tricks in his bag.
