The third season of High Maintenance may have been occasionally uneven in regards to tone or pacing, but I think one kernel of the season has always remained true and that is the determination of the creators to portray Brooklyn, and New York in general, as honestly, specifically and lovingly as possible. This, of course, does not mean that they shied away from the frustrating or aggravating aspects of life in the city in order to paint the city in a glowing light. They also, thankfully, did not do what many people do who create media about New York, which is to only show the New York life that now can only be bought for six-digits minimum. It’s easy to love New York when you never have to ride the subway, you know?
No, High Maintenance has always been about living in this city more than anything else. Way more than pot, that’s for sure. With each installment, before and including its HBO run, the series has tried to portray an array of experiences within the city, many of which are very unglamorous. But they all seem to have one thing in common, which is that the characters don’t want to be anywhere else. Even when everything else is terrible, some kind of beauty or solace can be found within the New York madness. This episode is a full tribute to that sense of community and home within a place that may seem, from the outside, to be a noisy, chaotic, impersonal mess.
Even when everything kind of goes terribly, some people still feel emboldened and excited by the energy of New York. That’s what we see Leonard (Reed Birney) go through during the first half of the episode. After a pretty lackluster, to be generous, agent showcase he arranged for his acting students, he spends a night getting very drunk with an old friend and becoming one of those New York strangers you see wandering the sidewalks at night. While drunk, he buys himself an ice cream cone and unbuttons his shirt, eventually happening upon the Guy, who engages him in some polite conversation before Leonard pukes on the sidewalk.
Back in Leonard’s hotel room, Reed Birney delivers some ace physical comedy with his attempts to right his phone’s stance while masturbating and failing terribly, eventually settling for holding the phone above his head—which leads to him dropping it on his face. He wakes up a few hours later and stumbles, nude, into the hotel hallway. He’s sober enough now to be able to panic and he eventually knocks on the room of one of his students and gets a creepy cape and mask they had used in their performance earlier. Wearing this Eyes Wide Shut-esque ensemble, he goes to the front desk and gets a replacement key. Of course, no one bats an eye during his entire night out. That’s definitely one of the better New York traits that pretty much anything unusual could be happening and no one is going to be bothered by it. During all of this, though, Leonard still expresses a desire to return to the city he left a while ago. He and his friend almost get run over by a bicyclist and he gets a thrill from it. Even when New York is rough and exhausting and even dangerous, it offers energy and a multitude of possibilities that can’t be found just anywhere else, and for some people—for Leonard—that energy is almost irresistible.
We leave Leonard to see what is happening with the Guy and he’s having, on the face of it, a rough day. We learn through a few text messages that Lee and the Guy have just officially broken up, basically calling it as a summer romance that just had a short shelf life, no big deal. Lee seems extremely casual and Zen about it all—as is her way, it seems—but the Guy maybe is a little more disappointed it didn’t work out. On top of everything, the Guy’s RV (Steve RV, let’s all remember) might have irreparable malfunctions. On top of that, Abdullah, the Guy’s selling partner randomly bails on working because he’s harvesting honey instead. When the Guy tells him that’s “not cool,” Abdullah just sends a shrug emoji in response. The Guy needs the day off too, though, to visit old high school friends who are in New York for a heartbreaking reason.
Sarah (Cassie Beck) and Brian (John McKeever) are married and parents to three kids and are in the city for the services of one of the best doctors for their youngest child Logan—an infant—and his cancer treatments. It’s inherently upsetting seeing such a small, helpless person hooked up to a chemotherapy drip, and even more so when being cradled by his mom who is trying to stay positive. Cassie Beck does a great job with her few scenes in this episode of conveying built-up exhaustion, despair, worry, and love through her face and her actions when she interacts with the baby and when she discusses things with the Guy. Even when she keeps things light, or jokingly tries to pants the Guy in front of her older sons, we can see the heartbreak happening constantly under the surface.
Sarah’s coping mechanism may be to act as relatively normal and head-straight-on as possible with her kids, but Brian seems like he needs a total mental vacation sometimes. That’s what he’s looking forward to when he goes out with the Guy and what he communicates when he tells his friend “we’re going out.” It’s what Brian needs to refuel and stay strong for his family. And so, the Guy, who has been enjoying the gorgeous late-summer weather of the day, takes Brian cycling through the city with the goal of seeing the sunset. They get their directions wrong, but regardless Brian has a great time cruising through the city with the Guy, letting everything drop away and getting in the flow of just moving from street to street.
Throughout the episode, we see several scenes, or hear snippets of audio, from a New York tour guide. This isn’t just an actor playing a tour guide, though, this is Timothy “Speed” Levitch, the tour guide of tour guides, doing what he does best and talking about the city he probably loves best. I didn’t know about Levitch’s renown as a tour guide and general philosophical cult figure, but it is the specificity that High Maintenance brings to its depiction of New York that allows me to learn about people like this. Levitch was the subject of a 1998 documentary directed by Bennett Miller (who has since directed Capote, Moneyball, and Foxcatcher), titled The Cruise. Over the final moments of the episode, we follow the Guy on his way through the city as he passes through recognizable and beloved locations, all while Levitch practices a new speech that suits the footage perfectly:
I suppose if I had an essential goal on the cruise right now, it would be to exhibit the fact that I’m thrilled to be alive and to still be respected. I suppose the soulful or the Buddhist out there might ask, “Why do you need respect from others? The thrill to be alive, that’s your own business. You can do that in your living room.” But that’s not what the cruise is for me. The cruise is about the searching for everything worthwhile in existence. I mean, I will appreciate the beauty of a flower, and then likewise, I will stand exhibitionistic and have the flower appreciate the beauty of me.
- This episode was written and directed by Ben Sinclair. This season has done nothing if not completely clarified Sinclair’s comedic voice. The bit with Leonard in the hotel now feels very distinctive of Sinclair’s sensibility.
- High Maintenance must be doing all of the heavy lifting for HBO in terms of getting their full frontal male nudity numbers up.
- How many times do you think the words “bro” or “bruh” were used in this episode? My conservative estimate is 30.
- The woman who interrupts the initial tour is played by Bari Hyman, who played basically the same person in Broad City’s season one episode, “Stolen Phone.” (She yells at Abbi and Ilana for stopping on the sidewalk in Times Square). I thought maybe she was a New York street legend, but she has a lengthy IMDb page. So are Broad City and High Maintenance in the same universe?? How great would it have been to see Ilana buying her weed from the Guy?
- If Levitch feels familiar to you (as he did with me), it might be because you saw him in Richard Linklater’s Waking Life. Linklater also directed a short travel series for Hulu in 2012, starring Levitch, called Up to Speed. It’s still streaming!
- The Guy’s farewell to Brian is “your family’s beautiful,” and it’s such a subtle, sweet, heartfelt and honest sentiment. It’s a great writing choice.
- The credits scene is New York at night time, and the song is “Do Your Best” by John Maus. It is BIG mood with very apt lyrics for High Maintenance: Someone’s alone in your city tonight/Reach out your hands to the one alone, in your city tonight…
- Thanks for reading and watching High Maintenance season three along with me! Part of me wants the show to live on and evolve forever, like a good parallel to SNL, but another part of me thinks this season finale would be a fitting farewell. Either way, I’ll always be watching.