Top 10 ‘High Maintenance’ Episodes Starring the Guy, a Lot of Weed — NYC

High Maintenance
David M. Russell/HBO ©2018 HBO

All highs must come to an end, High Maintenance included. After four seasons, the low-key comedy co-created by Katja Blichfeld and Ben Sinclair is not moving on to a fifth, the network recently announced. In both the TV show and the Vimeo web series that preceded it, Sinclair played The Guy, a bike-riding pot dealer whose deliveries were the through line connecting a wide cast of characters and slice-of-life stories. But The Guy was merely tangential in many episodes: New York City and its residents were the real stars of the show.

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If you’re taking your first hit of High Maintenance — or revisiting the comedy for the umpteenth time — here are 10 top episodes to “blaze” through.


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When you realize that Downton Abbey star Dan Stevens is playing a guy who secretly cross-dresses when he’s alone at home, you’re braced for the inevitable moment the character’s wife finds out. But the twist at the end of the episode subverts that expectation in a way that feels much more authentic.


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This tells the tale of a couple who, in an effort to save money, move from the Williamsburg neighborhood of Brooklyn, a stone’s throw away from Manhattan, to Ditmas Park in Brooklyn, which is much more of a hike, and then spend the episode trying to convince friends — and themselves — that the neighborhood’s perks are worth the long commute.


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In an innovative installment filmed from a canine point-of-view, a scruffy dog named Gatsby starts crushing on his walker— played by Orange Is the New Black star Yael Stone — and goes off-leash, so to speak, when the dog walker loses her job.


If for no other reason, watch this episode just for the scene where The Guy sees a cab-driving Obama lookalike and, in his rush to follow the guy, crashes into a pile of trash and channels that Kate-Winslet-on-a-door moment of Titanic.


Girls star Jemima Kirke plays a fictionalized version of herself in this episode, which also features Amy Ryan as a filmmaker who calls a “security meeting” with two colleagues in a ploy to get baked — and to escape the cursed, bee-infested film set.

‘Pay Day’

Comedian Margaret Cho plays one half of a queer Asian couple — a kind of pairing that, unfortunately, is still rare on TV —and even The Guy gets a taste of her character’s dominant side. Elsewhere, two teachers’ workplace affair literally costs them thousands of dollars through a cruel twist of fate.


As The Guy consoles a friend whose ex becomes a #MeToo target, this episode’s B-plot features a far sweeter story: The tale of a construction worker and a bodega employee who fall in love over the former’s “coffee regular” routine.


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The boundaries between (fictional) This American Life staffer Yara’s personal and professional life blurs when she mines a fight with her boyfriend for a radio story. Ultimately, though, it’s the American life of an overworked singing telegram performer that host Ira Glass — playing himself — chooses to profile.


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Another example of High Maintenance representing underrepresented identities, this episode delves deeper into the asexuality of Evan — a character fans know from the web series — as he goes on a date with Kym, a woman who works as an intimacy coordinator on film sets. Evan is asexual but not aromantic, as he explains, and he and Kym both detail their romantic needs and wants as they negotiate a potential relationship.


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In what is apparently the series finale of High Maintenance, viewers finally get to know personal details about The Guy as he forges a new connection with his niece on one blizzard-stricken Christmas Eve, while a group of stranded flight attendants share an impromptu familial moment of their own in a crowded “crash pad” in the city.