Talking to High Maintenance‘s Ben Sinclair Feels Like a Delivery From The Guy, In the Best Way

Going really deep with the guy behind The Guy before the season 2 premiere of his HBO series.


Now in its second season on HBO, High Maintenance, the cult stoner series co-created by Ben Sinclair and Katja Blichfeld, feels less like a smattering of loosely connected web vignettes and more like a television series, as the anthology gets deeper into the psyches of the customers—those strangers whose colorful lives are explored and examined without judgment—of The Guy, the unnamed protagonist played by Sinclair who bikes through New York to deliver weed. Notably, it begins to make clear that weed isn’t the real coping mechanism for life in 2018—or at least, not the only one. Not everyone “smokes their feelings away,” as Sinclair put it. In fact, we didn’t focus on weed all that much at all when we talked.

“We never wanted to linger on the weed element, even from the beginning,” Sinclair told me. In moving The Guy through the lives of his customers, it becomes clear that each of their uniquely mundane lives are what make them fascinating—these are the subway riders, the brunchers, the neighbors. “We wanted to use the delivery aspect as a gateway into things we felt were much more interesting than getting stoned. I love talking to people and having deep talks with people, and finding out what they feel about things and what they struggle with. I really like psychology, human psychology, and coping is a big part of that,” Sinclair explained.

“Thematically, I think about community a lot,” he went on. “We feel better in communities. And to be in one, you have to shirk off your individuality, which means that you have to sometimes repress things in order to fit within this support system of a larger community.” The New Yorkers in High Maintenance are colorful, dynamic, and only very loosely connected—but still part of the same fabric, nonetheless. In “Globo,” the first episode of season 2 which premieres on Friday, things open with New Yorkers looking down at their phones to see a news alert about an unspeakable unnamed tragedy of apocalyptic proportions. Customers call upon The Guy to deliver an antidote for what one character calls “a phantasmagoria of despair,” even if the tragedy never gets named. It’s not an unfamiliar moment in 2018, but the episode never relies on hackneyed tropes or tricks.

For Sinclair, sometimes figuring out how to sprinkle the weed element into the narrative can be the most difficult aspect of writing an episode. For example, the concept behind “Globo” was born on Inauguration Day last year. After spending time in the writers’ room, Sinclair and Blichfeld emerged for a break only to look down at their phones, finding themselves forced for the first time all day to fully engage with the news of Donald Trump being sworn in as President of the United States. “To see that it was actually happening, this pit appeared in my stomach,” Sinclair said. “Katja brings it up a lot, but Sex and the City never talked about 9/11. Which felt strange.”

Sinclair also took inspiration from Molly Fischer’s article “The Great Awokening,” in New York magazine, which he and Blichfeld feel encapsulates one of the goals for High Maintenance as a pop culture artifact of this era: “It’s a lot about our self-reflexive ability and the value of ‘wokeness’ and how that is the valued thing right now, to recognize the disenfranchisement or be sensitive to cultures that are not your own,” he said. “That’s pretty cool that it’s a thing right now, and we want to be a part of that.”

The concept of “wokeness” is handled on the show lightly, often skewering a class of the hipster urban liberal: There’s an episode in season 2 in which two lesbian moms invite a group of women into their apartment to make protest signs, possibly for a Women’s March anniversary protest; another that engages with the economic oppression of urban citizens and the housing crisis across many major American cities. Sinclair calls these vignettes “the ouroboros, or snake eating its own tail so to speak, of white guilt and wokeness.”

The Guy, arriving soon.


Fans of the series will also recognize some familiar faces this season: Greta Lee, aka “Homeless Heidi,” shows up, and the twentysomething iPhone addict and freelance writer named Anja returns for an episode that follows her documentation of a Hasidic Jewish man named Baruch; both are handled with equal amounts of humor and pathos. While examining the communities they were writing about, Sinclair found that there were many “traps” for him and Blichfeld, his creative partner (and now ex-wife), to navigate. “We’ll lose things if it feels too ‘on the nose.’ When we were writing that Hasidic episode, it really took a long time,” Sinclair said. “There were all of these ways to ‘otherize’ the Hasidic community, and we kept approaching it to be like, Yeah of course we could show a naive Hasidic guy coming into the world or this very black and white view, but what I noticed that was not being talked about as much was that New Yorkers who are not Hasidic were fascinated by Hasidic people, and ‘otherized’ them, and treated them like a subject of study, myself included. That community, they have achieved to otherize themselves but we also fall into that trap by overlooking their humanity.”

While the series is sensitive about the humanity of its characters, High Maintenance also owes its successful growth from web series to HBO show to digital culture. The modes of living in a society where connecting is often inhibited by our addiction to technology and social media are not easy to capture on screen, and while films like 2017’s Instagram fever dream Ingrid Goes West and TV like the dystopian Black Mirror come to mind) tend to come off as cautionary tales, High Maintenance actually takes the subject in stride, with optimism intact. “In some ways we’re the most peaceful we’ve ever been as a society. We have acknowledgement of civil rights and equality, and we’re not in serfdoms,” Sinclair said. “But we can talk about our fears through our megaphones. The thing that kind of describes the 2010s is anybody’s ability to express themselves. It can be clumsy and it can be hurtful, but it can also be super necessary. We have to learn how to use that limb.”

Down, not out.

That isolation imposed by our screens is palpable in High Maintenance. The Guy’s customers often call upon his services not only to get high, but because they want someone to talk to about their problems or share news (an earlier episode has a customer ordering weed from The Guy, but he doesn’t even smoke). Last season, it was revealed that The Guy lives down the hallway from his ex-wife, who has since entered a new relationship and moved in with a woman, revealing an insight into Sinclair’s character never seen when High Maintenance was a web series. “We’ve always wanted to keep The Guy a mystery and if you do learn something about him, it’s through somebody else,” Sinclair said. “Also, I have the luxury of being the main character of this show. I’m a white, cisgender male with my own television show. It’s not fair. I have all of the privilege, and I wanted Katja to have her platform as well because I knew that we knew we were splitting up, and we knew that it was important to keep the egalitarianism of the creation of this show intact.”

Blichfeld and Sinclair may have split up, and while they have written and directed episodes together in season 2, moving forward they will no longer work as a directing duo. “High Maintenance is a journal for us in a lot of ways,” Sinclair explained when asked about an upcoming episode that offers more insight into both The Guy and a character modeled after Blichfeld. “It is a metaphorical explanation of our lives and our relationship and our feelings. We’re so lucky that we have that platform with which to express ourselves. It is not quite literal, but it is pulled from the headlines of our lives.”

“Sometimes I describe me as the gas pedal, and her as the brake, and you can’t ride either one too hard,” Sinclair went on. “This show is a gift. We’ve been building the structure and community of people around this show for years. There’s nothing wrong with any of that. There’s nothing wrong with anything, really,” he added. “High Maintenance is the sweet spot where Katja and I agree.”

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