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‘High Maintenance’ Review: The First Great Web Series Is Now HBO’s Best New Show

The freewheeling look at modern New York life makes a smooth transition from Vimeo to HBO — and even manages to kick up its game.

Ben Sinclair in “High Maintenance”

David Russell/HBO

There wasn’t much competition for quality among web series when “High Maintenance” launched on Vimeo in 2012, but the show went beyond raising the bar to invent a whole new set of expectations. The self-distributed effort by couple Katja Blichfeld and Ben Sinclair provided a freewheeling mirror into the ironies and contradictions of modern New York, with a beautiful command of several tones that it juggled with ease. The appeal of this sprawling urban portrait, in which an amiable bearded weed dealer known only as The Guy (Sinclair) provided the only connective tissue, stemmed from the sense that anything and anyone could become a part of its ever-expanding universe.

Blichfeld, Sinclair and their army of close-knit collaborators developed a tapestry of small moments that spoke to a larger vision — a city that was funny, ridiculous, sweet and sometimes a little bit sad. Like the drug sold to new clientele in each episode, “High Maintenance” spoke to many sensibilities at once.

The show’s loose style seemed to reflect the autonomy of its creators, who maintained authority over the show’s direction even when Vimeo began to finance later seasons and its popularity took off. However, when it was announced in 2015 that “High Maintenance” had been picked up by HBO for a new season, the news perplexed many of its diehard fans. Could a show defined by its resistance to the clean, linear storytelling of mainstream programming keep its edge on cable?

So far, the answer is as exciting as a pungent new strand of sativa: In the six half-hour episodes that comprise the new season on HBO, “High Maintenance” exceeds expectations, not only delivering the same loose energy of the earlier seasons, but deepening the DNA of the show with the complicated tools at its disposal. Each episode, co-directed by Blichfeld and Sinclair, bounces around with a series of intriguing, colorful characters from so many walks of life it’s impossible to comprehend them all at once, or to anticipate what might happen next.

There’s no better example of the show’s increased scale in the sixth season than the episode entitled “Grandpa,” which takes place entirely from the perspective of a dog. That would be Gatsby, whose mostly faceless, Trump-supporting owner moves from the midwest to Queens and settles into a sad, lonely existence. Gatsby, on the other hand, embraces the setting thanks to a newfound companion, plucky Aussie dog walker Beth (Yael Stone), who may or may not be a romantic interest of The Guy. (We learn a few new details about the ubiquitous drug dealer in this season, but he’s still mostly the Greek chorus of a much bigger picture.) The camerawork in “Grandpa” is a masterclass in maintaining a single point of view, as Gatsby watches Beth with an adoring gaze whenever she comes by and eagerly awaits each new visit. When she abruptly drops out of the picture, he takes action to get her back, and the absurdity of this canine adventure builds to a touching finale that epitomizes the kind of unlikely balance between irreverence and emotional authenticity that the show pulls off so well.

In another way, “Grandpa” is an exception to this season, since it focuses on only one set of events. Usually, the show folds the snapshot approach of earlier episodes (which ranged in length from five minutes to around 20) into an anthology-like structure in which single episodes contain several overlapping installments. It’s a shrewd device that yields fascinating contrasts, with episodes that stretch across boundaries of age and class in a uniquely metropolitan fashion (it may in fact be HBO’s most diverse program to date, without forcing it).

Ben Sinclair in "High Maintenance."

Ben Sinclair in “High Maintenance.”

Craig Blankenhorn/HBO

One of the best installments in this regard is “Museebat,” the second episode, which brilliantly compares the experiences of a rebellious Muslim-American college student (Shazi Raja, a true discovery) with the bourgeois concerns of her swinging older neighbors (Lee Tergesen and Amy Ryan, whose hilarious performance points to the show’s growing profile).

Likewise, in “Tick,” the story of an older Chinese immigrant (Clem Cheung) making a living nabbing bottles from recycling bins dovetails into a moving story of the man’s relationship to his assimilated grown son. That drama then shifts to an unrelated set of characters, retired partier Jim (Peter Friedman), who indulges in morning raves while his married daughter (Bridget Moloney) watches disapprovingly from upstairs. Their unruly relationship finds her struggling with adult anxieties and his attempts to escape them.

The undulating possibilities of this father-daughter tale outdoes anything found in traditional stories of broken families produced in more traditional terms. It’s a sophisticated look at intergenerational conflicts boiled down to a matter of minutes. (The dynamic echoes the one found in Cannes favorite “Toni Erdmann,” released in theaters later this year.)  The episode’s coda — which ends, as they all do, in a slo-mo, quasi-operatic riff on its themes — finds The Guy encountering a drama deeper than anything he can comprehend in his insular world. That’s the essence of “High Maintenance,” where everyone’s so trapped in their personal stories that only the weed provides them with a modicum of escape.

READ MORE: ‘High Maintenance’ Trailer: The Weed-Themed Web Series Finally Makes Its Way to HBO

Of course, with such flexibility to its approach, not every episode reaches for the same euphoric highs. While “Selfie” opens with a brilliant meditation on the destructive impulses of social media, it eventually shifts into a discardable escapade that includes the set of “Girls,” an irreverent Hannibal Buress cameo (though, to be fair, he has been on the show before), and the return of the notorious “Homeless Heidi” (Greta Lee), who drifts from one home to the next by choice. When Heidi reaches out to The Guy for help, the ensuing plot includes a meta-twist on the show’s very existence that’s cheekier and more disposable than other installments.

But you can’t win it all on a show willing to try anything, and that’s exactly what makes “High Maintenance” so welcome in a sea of conventional television narratives. The biggest reveal of the season comes from the finale, which just barely hints at a greater backstory about The Guy than earlier seasons ever bothered to provide. But that’s all we really need in terms of forward progression on a show that tends to jut off in a dozen directions at once.

As a whole, “High Maintenance” suggests its universe knows no bounds — as long as The Guy’s around to deliver the goods, its premise can eternally expand outwards to encompass new characters and ideas. That’s a welcome antidote to the usual expectation that all commercial programs must reach for a tidy conclusion, or face the threat of cancellation. Let’s just hope that HBO keeps buying the good shit.

Grade: A

The sixth season of “High Maintenance” premieres Friday, September 16 at 11:00pm on HBO. 

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