Ben Sinclair, OC ’06, co-created the hit web and television series High Maintenance with spouse Katja Blichfeld. The show revolves around the experiences of New Yorkers connected by their shared transactions with a pot dealer known as The Guy. Meant to tell subtle truths about the human experience while de-stigmatizing marijuana use, the series focuses on different characters and stories with each episode. After two seasons on Vimeo featuring mini-episodes, HBO picked up the show. The new season, comprised of six 30-minute episodes that each contain multiple intertwining narratives, has garnered widespread critical acclaim, prompting renewal for a second season. Sinclair joined the Review for a phone interview to talk about his time at Oberlin and his creative process.

Students can watch both the miniseries and the new season — as well as the rest of HBO’s online entertainment library — via HBO Now with a college discount at $9.99, or can try the service out with a free 30-day trial. 

This interview has been edited for length and clarity.

I’m a big fan.

Oberlin was so instrumental in my success in so many ways that I am so happy to do whatever we need to do for the school short of spending all of my money again on that.

I know you returned at one point for a festival?

About four years after I graduated, they started the Oberlin Theater Festival, and I came out for their initial year of that and played Caliban in a production of The Tempest … But I did kind of realize when I came back there that year that Oberlin was very special, but it was also the time and not the place. … A lot of people get out of college, and there’s this little bit of an identity crisis, and it was interesting to go back to college after four years — the time I had been in college — thinking that college was the best time of my life, and realizing, “No, life just began.” It takes a second for the suffering of not being supported 24 hours around-the-clock to wear off, but it’s cool, man. It’s good to be an adult.

Were you involved with theater at Oberlin?

Yes, I was. I was a Theater and Dance major. I went thinking that I was gonna be an international relations major or something like that, that I felt was more important socially than theater and dance. But there was so much reading in the entry-level courses, and then that classroom was across the street from the theater and dance building where they were having an open house, and I just walked in and really got into it. Got pretty far into it. I spent almost all of my Winter Terms doing a play at Oberlin. … It was just friggin’ awesome to feel so supported. … College is so incredibly catering to this comfortable bubble after high school that it’s just incredible when you look back, like, “Oh my god, that was really easy.” But it was definitely customized for me. … I went back to the 10-year reunion, and it was really interesting, because there were some fans of the show there, and there was a lot of fear about what happens [after college]. … It was interesting to see Oberlin as a place with cell phones now that didn’t just have a bunch of acts happening on campus. Instead the acts were reverberated out into the world and then came back to them.

Oberlin is definitely an echo chamber, but it is also very loud, and heard by many.

Definitely. You know, before phones, that loudness, you could just do [things] safely on campus, and you could go way to the left as far as you could, and you could maybe do some things that seemed maybe kind of silly but experimental at the time. It’s just like, a safe space for just pursuing who you were, and it’s interesting now that … when the rest of the world hears about that information, it doesn’t feel like it’s such a safe space anymore. It feels more loaded.

What was your relationship with pot at Oberlin?

I didn’t really start smoking pot in a pothead sort of way until my senior year, and I was also training for a marathon, so I would get real stoned and run around Oberlin. … During that time, there was a lot of uncertainty about what to do after college, and … I think I was just more contemplative. I think more than pot culture, what affected me artistically was the interest in [Anton] Chekhov that [Associate Professor of Theater] Matthew Wright instilled in us my junior year. And what I learned with being interested in Chekhov … was that people don’t say often exactly what they’re thinking. People largely aren’t emotionally intelligent enough to do that. So you would have to decode these Chekhov scripts with these characters who were just saying very banal, day-to-day items, but then you would have to kind of be curious about what they were actually thinking. And then in that, it was the discovery that the little moments are way louder than the big plot explosions — that the little moments, and the little choices that people make every day, are what makes them what they are. So I think I [developed] a huge attention to human behavior, while also being an anxious person who wasn’t very good at feeling his feelings, so I would smoke pot to kind of quell the bad feelings. And only now am I learning at 32 that you can’t selectively numb feelings, that you’re also numbing joy when you numb pain. … So, it’s an interesting balance that we all have to get. … A lot of that growth started there. And that critical thinking started at that school.

I see a lot of Chekhov in the way you and Katja write your characters.

I think it’s interesting you say that, because I feel like as creators, we’re dropping hints about these characters. And very rarely do we have them say exactly what they feel, or exactly what they mean. So, I think you as a viewer are doing a lot of the work of instilling the world of these characters, but we are giving you hints that may align with your experience as a human being and may guide you to make judgments about this person, why they’re acting the way they are. But in the end, we’re just putting pictures and sounds together and dropping clues.

You have such a wide variety of people in these episodes. When you approach writing a character that might have had experiences that don’t align with your own, how do you cross that bridge?

I mean, whose experience doesn’t align with our experience? I know that people are given different circumstances, but all people deal with hunger and pain and joy and all sorts of complications, wanting one thing but being presented with another thing … extends across all socioeconomic backgrounds. We do like to acknowledge the reality that class and race are largely not as integrated as many of us would wish in this country, so we have definitely made it our goal to be more inclusive in the lives that we are portraying, but the underlying feelings of all these characters … are feelings that we feel, and we just kind of put them under other people’s skin. … It’s all coming from a collective human experience that we hope we are expressing in a way that feels relatable.

How does that translate to the way that you direct your actors?

Our original purpose [in the miniseries] was to create a community of artists who we could work with and not ask too much of. When an actor came on set, we’d make sure that they knew that this part was for them, so we didn’t ask them to audition, we just called them or emailed them and said, “Hey, we wrote this part, we were thinking of you, do you wanna do it?” And then when they got on the set, we’d say, “Hey, it’s you. Just bring [yourself] to this. And if the line doesn’t feel right in your mouth, then change the syntax; then find another way to say this that makes sense coming out of your mouth. But we trust your inner life to come out, and we’ve got you. We won’t make you look bad. That’s not what we want.” And I think just giving that kind of trust to an actor was really helpful in letting them feel safe to lend us their personality and their vulnerability.

Do you bring yourself to The Guy in that way?

Yeah, I think The Guy is how I would like to be. But … a lot of people put this shaman-esque kind of judgment of him, like he’s this great guy who’s always willing to help anyone and that stuff, and that is part of him, but he’s really just a guy. And we’re purposely not letting people know everything about him because we’re aware that you as a viewer are gonna make him whatever you want him to be, and in some ways that’s more interesting than finding out a name or a past. We want people to feel good about him, but also people want to feel good about him, too. So we are using that to our advantage by revealing less.

Do you ever wish that you got to play some of the more out-there, bombastic characters in the show, or is there more catharsis in just watching your stories unfurl?

Oh, god. Being an actor is really lacking in agency. You don’t have a lot of say over how you are represented in the end. You know, the editing makes the film, and you can manipulate a performance so crazy much in editing that it’s frustrating as an actor to be like, “I feel like I have good ideas.” And I spent, at the time, 40 grand a year at Oberlin to try to build up my mind. I didn’t say that, [it was] all [to] myself, but you develop this mind and critical thinking and you study Chekhov and think about all these things and it’s so much more gratifying to see your brain doing the work. And this show is a journal, you know? Many people have scrapbooks, I’ll have episodes.

In theater you really do get to control the audience and control how they see you, but in film not so much.

You know what’s great about doing both, though, is I get to use my brain and my heart. A lot of times, the temptation is to get very intellectual, and … not always, but there’s a lot of men out there who write scripts with these huge plots and all these twists and turns and whatever, and then you’re like, “Gosh, I don’t know this person because their heart isn’t there.” You can’t see their heart. So, you know, as an actor, and [with] all the training from acting, I think I’m a little more in touch with presenting my heart.