When you think of the characters who have defined HBO’s programming over the past two decades, several names come to mind: Tony Soprano, Carrie Bradshaw, Daenerys Targaryen, Hannah Horvath, Issa Dee. But there’s one character who stands out because he doesn’t have a name at all: the weed dealer who bikes his way around Brooklyn on High Maintenance.
“The Guy,” as he’s referred to outside the series, is the show’s one constant. Over the course of its two seasons on HBO (and six seasons as a web series before that), High Maintenance has told the stories of all kinds of New Yorkers spread across the city, their lives linked only by the dealer they employ. As played by Ben Sinclair, who co-created the series with his creative partner and then-wife Katja Blichfeld, The Guy has largely been the platonic ideal of a weed dealer: amiable, consistent, and willing to listen to your problems without burdening you with any of his own. At times, he has been less a character than a narrative device, a way of unifying disparate groups of people who, on paper, have little in common.
But in High Maintenance’s HBO iteration, something unexpected has begun to happen: The Guy, once more a concept than a person, has become a character in his own right. We started to get a sense that he had a life outside delivering weed. His zen facade dropped when his bike was stolen. He got antsy and lonely when he was sidelined by an injury. We even met his ex-wife (Kate Lyn Sheil) and her girlfriend (Rebecca Naomi Jones) in a storyline that mirrors Sinclair and Blichfeld’s marriage. (Blichfeld came out as a lesbian after the divorce.)
When the third season premieres Jan. 20, High Maintenance will continue to explore The Guy’s life while also showcasing the stories of the customers he delivers to. “I anticipate that that will be the criticism of this season,” Sinclair told BuzzFeed News. “There will be camps of people who want to see more of [The Guy] and camps of people who are like, the show is not successful because of him.”
Sinclair admitted that he and Blichfeld were worried about undermining the mystique of the character by delving into his personal life. The first episode of the web series originally included a monologue of exposition that they ultimately ended up cutting; after that, they decided to leave The Guy deliberately vague. On HBO, however, as the writers have continued to be inspired by their own lives, Sinclair has allowed more of his reality to shape the character.
“The second season, it was me and Katja divorcing while working on the series, so I just wasn’t able to think about anything else in a lot of ways,” he said. “This [season], it’s about The Guy’s romantic life more so. I have dated three people quite seriously since breaking up, so I had been doing a lot of that kind of soul-searching myself.”
As Sinclair later summed it up: “This third season is like, Oh, he’s got wants and desires outside of selling weed.”
It can be a challenge to distinguish an actor from their most notable role, but it’s even harder to separate Sinclair from The Guy. The character has clearly been drawn from his portrayer’s life: Even the RV The Guy is driving on High Maintenance is the actual RV that Sinclair bought on Craigslist as “one of my weird post-divorce things that I did.” For a while, he was frustrated when fans interacted with him as though they were talking to The Guy, but he has largely gotten past that.
“When I want to separate myself from that character, I also think to myself, Dude, you may never have a platform ever again. You could die tomorrow,” he said. “I am happy to marry myself to that character, ‘cause he’s pretty cool. He’s like the better side of me.”
It’s also somewhat easier for Sinclair now that The Guy has been allowed a bit more complexity: People no longer seem as surprised that in real life, Sinclair himself is not their perpetually even-keeled stoner friend. “This comforting illusion that The Guy is not just a guy, that he’s a monk, that he’s a spiritual bum, or that he’s some Buddhalike figure, people did project that onto me in public, and I didn’t like that feeling,” he said. “I’m just a person. I get angry and I get scared and I feel tired. The Guy smokes a lot of pot too. Chances are there’s something he’s numbing.”
But it makes sense that The Guy has developed into a real person with real problems. If there’s one theme that High Maintenance has driven home beyond all others it’s that, in one way or another, everyone is going through it. It’s true, of course, that some people have it easier than the others, but in its intimate telling of these slice-of-life stories, the show has reminded viewers that we don’t know exactly what bullshit anyone else is dealing with. As many on Twitter and beyond have noted, it’s a little like Humans of New York. Except, you know, good.
That’s largely because the show’s “everyone is connected” ethos is realistic about the limitations of that perspective. There’s an admirable sincerity to High Maintenance, not to mention real compassion for these characters, but there’s also cynicism and a sometimes bleak emotional honesty. Because if there is a common thread to the New Yorkers depicted on the series, it’s that — even in a city of 8.6 million people — they feel isolated and lonely. Maybe that’s why they smoke so much weed, which Sinclair notes has a distinctly numbing effect.
Of course, there are plenty of reasons why people might want to check out of reality, especially in 2019. If last season, which began with the city reacting to an unspecified act of terror, was about coping with Trump-induced trauma, this season is about — at the risk of bumming everyone out — moving on and acknowledging the inevitability of death.
“In the first episode someone dies that makes the character have to look introspectively,” Sinclair said. “The Guy has to think about his mortality, and he chooses not to for most of the season. He kind of just distracts himself with sex, the same way that people numb themselves with weed.”
That, too, came from what Sinclair and Blichfeld were observing about their real lives. “Everything seemed like it was dying,” he said. “There’s a lot of death in this season. And it’s like we’re saying, ‘Life goes on, and we’re all gonna die.’”
Yeah, heavy. But Sinclair isn’t actually your most depressing friend at a party, and High Maintenance is still filled with humor and a genuine affection for New York that has made viewers get so attached. It’s that love for the city — this season, the show filmed in all five boroughs — that staves off the bleakest feelings, giving the series a warmth that invites you in even as it shares harsh truths. For Sinclair, who said his most meditative moments are when he’s riding his bike around New York, that’s the perfect reflection of life in the city.
“All you have to do is just look around and be like, ‘Whoa, I live in New York City, what the fuck,’” he said. “That’s incredible. Even that alone.”
Outside of his day-to-day life in New York, Sinclair has a lot to be excited about when it comes to High Maintenance: This season, the series moves from its Friday night slot to the more coveted Sunday night lineup, which should bring in new viewers. And while making the series is hard work, it’s also been a joy for Sinclair, who said, “I went into this year being like, I want to be around what lights me up. I want the people in the room that light me up.”
That doesn’t mean he’s not thinking about the end. It’s true that High Maintenance could go on indefinitely: There will always be stories about New Yorkers to tell. But just as The Guy is imagining what his life could look like after he stops selling weed, Sinclair is considering what his life could be once he’s done making the series. There’s also something compelling to him about ending the show at a creative high point, even if, he acknowledges, “That’s not a very capitalist thing to do.”
“I work on a show with my ex-wife. It’s great. This year we’re having a blast together actually in a way that seems so evolved,” he said. “But we also have to build our own lives as directors, as creatives, and the show does take a lot of time, so I want to finish the show on a good note and try to let the community that has built around the show sustain it for more years.”
That’s not happening tomorrow, but it will happen at some point down the line. As Sinclair is determined to remind us, everything dies eventually, even TV shows. Sounding more zen than ever, he added, “Nothing lasts forever.” ●