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A Beginner’s Guide to HBO's High Maintenance

Four seasons in, it’s not too late to let this critically acclaimed semi-anthology series bowl you over.
  • "The Guy" (played by series creator Ben Sinclair) is the enigmatic center of High Maintenance. (Photo: HBO)
    "The Guy" (played by series creator Ben Sinclair) is the enigmatic center of High Maintenance. (Photo: HBO)

    When it debuted on HBO in 2016, expanded in length and scope from its original run as a 17-episode webseries, High Maintenance seemed like an odd fit for the premium network. Dreamy and deeply humanistic, the anthology series about all the people connected to a New York City pot dealer seemed too sedate to be an HBO comedy, and too sweet to sit alongside antihero fare from the network that brought us The Sopranos and True Detective.

    But HBO’s experimental phase, which has paid dividends that include Watchmen, Sharp Objects, Euphoria, and Los Espookys, has carried this gem of a show along into its fourth season, which premieres Friday. If you haven’t kept up with the show, the good news is that it’s a supremely easy series to dip into, with very little mythology or ongoing narrative arcs as barriers to entry.

    What’s the show about?

    Imagine a fictionalized Humans of New York: a beautifully shot, incredibly well observed collection of stories about individuals and their unique foibles and minor triumphs. The series effectively straddles the line between stoner comedy (the show doesn’t opt for cheap laughs in this area) and urban melodrama. Episodes usually run about 25 minutes. and consist of two separate stories focusing on a person, a couple, or even a very interesting animal. Sometimes the stories have a loose connection to each other or a thematic idea in common, but not always. The main thread tying all the stories together is that The Guy (star and show co-creator Ben Sinclair) deals marijuana to or has interactions with someone. The credit sequence often is a feel-good slow-mo moment of Zen featuring The Guy or a character from that episode.

    Why do critics love it?

    Although some felt the transition from short-form webseries to sitcom-length HBO series was a little bumpy at first, High Maintenance has generally received high marks from TV critics who have praised the show’s evolution. The New Yorker’s Emily Nussbaum said of its second season, “It never feels contrived, because the stories seem spontaneous, as natural as a train of thought. It’s a remarkable achievement of narrative efficiency, fueled by humility… It doesn’t judge. It doesn’t look away.”

    Spencer Kornhaber at The Atlantic called the show “a gentle work of sociology, asking who people — all sorts of people — really are, and not harshly judging the answers that it discovers.”

    And James Poniewozik of The New York Times was still a fan of High Maintenance as it went into its third season last year, writing, “The show combines a winning slacker charm with a detail-perfect sense of life as lived, right now, in its slice of the city. It embraces its oddball subjects — con artists, Craigslist obsessives, exhibitionists, even dogs — and the city that, for all its demands, gives them the space to be who they are.

    What’s with “The Guy?”

    Part of the fun of the show’s run has been how little we know about The Guy, the show’s unnamed weed dealer. Over time, in drips and drabs, it’s been possible to piece together parts of his life, even though the show is about 90 percent not about him. We know that The Guy is divorced from Jules (Kate Lyn Sheil), a brand strategist who left him for a woman named Gwen. (This mirrored the real-life breakup/divorce of Sinclair and show co-creator Katja Blichfeld.) Despite this, The Guy and Jules are still on good terms. The Guy relies on his cellphone for his business dealings and has a wide range of customers across the city he reaches on bike. But he also seems a bit ambivalent about technology and is into analog comforts like swimming, reading a book in a hammock, and living in an RV for a while.

    He is extremely laid back and not at all judgmental unless he comes across rude people (such as the bros he identifies as “Assholes” on his cell phone) or people who try to base a TV show on his life (Homeless Heidi in “Selfie”) or try to write an expose on him (Anja in the same episode).

    Know Your High Maintenance strains

    Although the show has a generally positive and warm view of humanity, individual episodes can sometimes be broken into types. Here’s a starter guide to five episodes by you can watch ahead of Season 4 to give you a pretty good idea of what you’re in for:

    Heartwarming: “Grandpa” (Season 1, Episode 3) A story told from a dog’s point of view, this one’s about a lonely canine named Gatsby with a struggling owner (new job, new apartment, recent breakup). Gatsby falls in love with a beautiful dog walker, a woman who happens to be dating The Guy. This one’s a little on the twee side, but what a great dog performance from Bowdie, who plays Gatsby.

    Topical: “Globo” (Season 2, Episode 1) An unnamed catastrophe creates anxiety in New York and is the topic of nonstop discussion as The Guy tries to go about his day. Airing just months after the 2016 presidential election, it could be taken as a mood piece about fears many people had going into 2017.

    Cautionary: “Fingerbutt” (Season 3, Episode 6) High Maintenance usually has a “Handle your high” philosophy about marijuana, but in this episode, microdosing does not go well and it leads to a very, very traumatic incident inflicted by a veterinarian. You can skip this one if harm to animals is a nonstarter for you.

    Meta: “Selfie” (Season 1, Episode 5) Several episodes of the show feature real-life celebrities playing themselves, or pop-culture properties being discussed in some way. In this one, a street filming of another HBO show, Girls figures into the story, and Hannibal Burress guest stars as a version of himself, mentioning that he can’t appear on HBO because of his contract with Comedy Central for Broad City (so meta!). But things get really weird when a TV adaptation of Homeless Heidi (Greta Lee) features a doppelganger of The Guy played by Brett Gelman.

    Episodes about The Guy: “Cruise” (Season 3, Episode 9) Season finales of the show tend to give us an idea of where The Guy is in his life or his romantic entanglements, and this one is no different. Even more of a love letter to New York City than usual, this one starts with a breakup, cruises through scenes of some very strong friendship bonds in The Guy’s life, and ends with a gorgeous ride through the city’s streets. It’s sweet and a little sad and a wonderful pause before whatever comes next season.

    High Maintenance returns with its fourth season premiere Friday February 7th at 11:00 PM ET on HBO.

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    Omar L. Gallaga is a longtime technology and culture writer with bylines in The Wall Street Journal, NPR's All Tech Considered blog, Rolling Stone, The Washington Post, CNN and the beloved TV websites Television Without Pity and Previously.tv. He's a former newspaper journalist who now lives in New Braunfels, Texas. You can find him on Twitter @OmarG. 

    TOPICS: High Maintenance, HBO, Ben Sinclair