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Since High Maintenance first premiered as a modest webseries in 2012, a lot has changed. The show’s DIY success led to Vimeo funding new original episodes on its platform, which paved the way for an HBO acquisition. Formerly married co-creators Ben Sinclair and Katja Blichfeld divorced between the first and second HBO seasons, though they both still work together on the series (Blichfeld has since come out as queer). The show has survived two different presidential administrations, and its Obama-era cultural idealism has subsequently found new purchase in a different political context. Not to mention marijuana has now been legalized in 11 states and decriminalized in another 15. In 2020, a weed delivery guy is a practical reality for much of the country and not some Brooklyn stoner fantasy.

At the same time, High Maintenance itself has remained consistent in framework and outlook. Each episode still follows a different set of New Yorkers who all purchase pot from The Guy (Sinclair), our nameless audience surrogate. While the character has developed and deepened over the course of the series, The Guy still mostly flits through other people’s lives already in progress. High Maintenance continues to balance slice-of-NYC-life observations with tight short-form structure: episodes often build to a reveal or a revelation; sometimes two different threads converge in surprising ways; emotional climaxes manifest unconventionally. The series retains a satirical edge, usually when depicting obnoxious yuppies or stereotypical millennial behavior, but it’s too gentle for it to ever draw blood. Sinclair and Blichfeld have fine-tuned a brand of grounded, casually diverse character-driven storytelling that maintains a remarkably humble tone. At its best, High Maintenance’s style of ever-expanding humanism makes room for everyone to be the center of the narrative.


But like many shows that have been around long enough to showcase their big bag of tricks, High Maintenance occasionally falls into stale, predictable patterns. An anthology series might promise infinite flexibility, but ultimately the lack of boundaries becomes its own limitation, and the weakest High Maintenance episodes tend to resemble bland, Humans Of New York-esque pablum. However, in the first two episodes of the upcoming fourth season, High Maintenance acknowledges its own formula through an implicit comparison with another longer-running series and good ol’ fashioned recursive meta commentary. “Cycles,” the season premiere, primarily follows a fictional This American Life staff member, Yara (Natalie Woolams-Torres), as she struggles to put together a piece about her parents’ marriage for a recycling-themed show. When it becomes clear her parents won’t go on the record, she openly speculates about their reasons with her boyfriend, Owen (Marcus Raye Pérez), on their anniversary. While discussing received ideas of womanhood and socially constructed gender roles, Yara accidentally strikes a nerve regarding Owen’s professional ambitions that culminates in a relationship-destabilizing argument, all of which she captures on tape.


“Cycles” features the real This American Life staff (including longtime host Ira Glass), films in their actual New York offices, and recreates a pitch session for an episode of the show. It’s not a leap of logic to suggest that High Maintenance proposes a parallel between both programs, with TAL’s all-staff meeting acting as a simulacrum of the High Maintenance writers room. Both shows incorporate real-life exploits that fit into a broad thematic umbrella, one which reflects upon the collective human experience. While one traffics in short fiction for television and the other journalistic nonfiction for the radio, both have an active interest in spotlighting small gestures and underserved stories that don’t receive much attention. TAL functions as a useful model for High Maintenance as a viable long-term project, but “Cycles” also suggests how these codified storytelling structures inevitably reduce life’s difficulties to its most salient bits. In the episode, Owen becomes furious when he realizes that Yara is recording their fight on tape; later, when she plays the recording for the TAL staff, the team inevitably discusses their possible breakup in terms of its value as a radio piece. There’s a self-awareness of how the most spontaneous moments from life can be cannibalized for the purposes of entertainment or journalism. The episode ends on a sweet note and features a classic High Maintenance dovetail between two seemingly disparate stories, but its self-critical dimension expresses awareness about the show’s own systemized nature, and possibility its own restrictions.

The second episode, “Trick,” follows two stories of intimacy struggles that also incorporates self-commentary about High Maintenance’s filming process. The episode’s first half follows Matthew (Calvin Leon Smith), who hires a novice escort (Jay Jurden) for an evening of “the boyfriend experience.” The two men share awkward conversation about identity and the cleanliness of Matthew’s apartment, but their encounter becomes even more strained when Matthew attempts to simply cuddle with his hired paramour before they become physically intimate. The second half of “Trick” chronicles a few days in the life of Kym (Abigail Bengson), an intimacy coordinator who works on film and TV sets, as she falls for Evan (Avery Monsen), an asexual man whose intimacy boundaries are well defined.


Blichfeld, the episode’s director, stages a physically and emotionally embarrassing scene that necessarily requires an intimacy coordinator, a mandatory policy, since October 2018, for any HBO show that features sex scenes, before shifting to documenting an intimacy coordinator’s own interpersonal struggles. On some level, this is cutely self-referential, but it also illustrates an eagerness on the part of High Maintenance’s writers and directors to foreground aspects of its own creation. High Maintenance has always been an emotionally vulnerable show (the series’ initial modus operandi was to literally enter New Yorkers’ apartments and private spaces), and it’s possible that vulnerability will extend to the series’ structural scaffolding as it goes forward.

While High Maintenance potentially moves in more meta directions, there are still some familiar pleasures by way of The Guy, who has adopted a stray blind dog and returned to the bike as a mode of transport after living in a rickety RV last season. The series continues to follow his struggle to preserve a self-sustaining lifestyle and career outside of society’s narrow constraints. Sinclair continues to be one of the best actors on television in part because his natural charisma and compassion extends to a character who feels stuck out of time: a roving avatar of kindness that offers relief and concern for people just struggling to maintain. As much as High Maintenance changes or stays the same, that’s one constant audiences can depend upon.


Vikram Murthi is a freelance writer and critic currently based out of Brooklyn.

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