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The unexpected and boundless generosity of HBO’s High Maintenance

Yes, the show is about weed — but also sex, fear, love, and the humanity that unites it all.

HBO’s High Maintenance, season 2
The Guy (Ben Sinclair) pays a necessary visit to a woman on the verge (Alex Auder)

Walking just about anywhere in New York City, I find it almost impossible not to flick my glance upward at the apartments above, each glowing with its own stories. I never stop, but certain things will stick with me: a flash of neon TV, a pointed shard of an argument, a winding line of music pouring out the window onto the sidewalk below. Lives stacked on top of lives, thrumming with their own energy and purpose, unfolding behind walls I’ll never break through.

I’ll freely admit that this favorite pastime of mine is maybe, just maybe, a little bit creepy. Still, I was relieved to find a show that’s not just sympathetic to this instinct — voyeurism rebranded as curiosity — but finds a way to indulge it with overflowing empathy.

HBO’s High Maintenance, which wrapped its stellar second season on March 23, began as a web series in 2012 that quickly proved itself to be more than its trendy synopsis of a weed delivery guy making stops on his New York City route. The Guy — played by Ben Sinclair, the co-creator and director of much of the show with Katja Blichfeld — winds through the city with open awe at all he gets to see. His favorite part of the job is meeting people, spending time in their homes, and getting a closer look at all the lives he’ll never live.

Each episode tells at least two stories, but more often than not, the show meanders through experiences like the Guy on his bike, picking up fragments of conversation and following them until something else catches its eye. Experiences range from the low-key (friends wanting a weed fix for a birthday) to the cutting (a self-absorbed Vice writer feigns interest in a former Hasidic man for a story) to the joyful (an eclipse party turns into an engagement party) to the heartbreaking (a city reels in the aftermath of some unnamed cataclysmic event).

In the second season, High Maintenance dug a little deeper and got even more ambitious. The premiere (“Globo”) made that plain with an entire episode focused on the city in mass mourning, following the undulating reactions of people crumbling in on themselves and/or trying to find some comfort in each other. Starting from that devastating point, High Maintenance’s usual standard of getting as up close and personal as possible without characters smudging the camera lenses felt even more urgent and precious.

Baruch (Luzer Twersky) meets a charismatic stranger (Natia Dune) after leaving his Hasidic community behind.

Every glimpse behind a closed door became a window into the lives of people just trying to keep themselves stitched together. Every single apartment has its own clutter and character, making it that much easier to step into someone else’s story for even just a minute. (This season, production designer Akin McKenzie was nothing short of a wizard.)

And yes, many of these people are the kinds of restless 20- and 30-something Brooklyn transplants that TV has come to love. And sure, the show often presents New York in its shiniest moments with the most potential for fun, a city in which a pair of cops on bikes see a total eclipse party in the park through a puff of weed smoke, and shrug.

But High Maintenance makes a couple crucial choices that keep its New York from feeling stale. For one, the show actually casts a diverse swath of actors that somewhat accurately reflects how the city actually looks. For another, it only shows a sliver of their lives, dropping in for specific moments that quickly become pointed. There’s a guy who tries (and fails) to go cold turkey on the constant onslaught of social media; a woman who tries (and fails) to fix the fact that her political protest group is all white; a couple who win a housing lottery and land in a new luxury building that reserves its best amenities for the people who can pay for them.

These chapters often target privileged obliviousness — but they’re also, crucially, not the only stories concerning this demographic that High Maintenance wants to tell. The show regularly upends expectations by introducing a millennial character who would be the focus of any other show, only to pull back and follow someone else instead.

A pair of parents (Marcia DeBonis and Ray Anthony Thomas) crash their daughter’s trendy neighborhood, are the best.

In one of the most purely delightful segments of the season, a couple go to visit their daughter in Bushwick, a Brooklyn warehouse district now swathed in fluorescent graffiti, and giggle their way through a chaotic night in an Airbnb loft. Their daughter’s life confuses them, but they’re interested in understanding it — even if it means accidentally spending the night with a stranger’s pet snake. In one of the season’s best episodes (“Derech”), that Vice writer — who appeared in the first season as one of the Guy’s least favorite clients — is a sidebar to the story of Baruch (Luzer Twersky), who left his Hasidic community and is now trying to not just make his way in an unfamiliar world but have some actual fun in it.

This season also made a bigger point of making the Guy more of a character in his own right, rather than just the happy-go-lucky conduit for everyone else’s experiences. That instinct is best exemplified by “Scromple,” an episode that opens with a therapist trying to draw boundaries with a needy patient in a way that makes it seem as though we’ll be following her for the next 10 minutes, as is the High Maintenance way. But 30 seconds after it follows the therapist out of her office, she ducks into the street to avoid her patient — and sends the Guy flying over his handlebars and onto the street. She hastily leaves him there, at which point the episode leaves her too.

The accident sends the Guy to the hospital, where he has to call his ex-wife — another character we’d never met before this season who ends up with her own storyline — so she can help him with her insurance. He also ends up with a cast on his arm. This leaves him unable to bike as he used to, sending him on a season-long journey to figure out who he is outside his deliveries. The truth is unflattering and lonely — but it’s also the truth, and it sparks growth he’s never showed before in the run of the show.

Giving the Guy more dimension was both a departure for High Maintenance and a move exactly in line with its empathetic ethos. Every character on this show is searching for some kind of spark to reignite their fire, whether it’s weed, or sex, or art, or friendship, or who knows, maybe just a really good slice of pizza. In the keen (if slightly bloodshot) eyes of High Maintenance, every single person onscreen — from the excitable tourist parents to the countless lonely people shuffling around their apartments — is worthy of having their story told.

The first two seasons of High Maintenance are currently available to stream on HBO Go.

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