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“Nothing’s Ever the Same”: Talking to Ben Sinclair About ‘High Maintenance’ Season 2

The beloved HBO weed show returns this weekend

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High Maintenance, the HBO anthology series about a Brooklyn pot dealer (Ben Sinclair), known simply as The Guy, has lived many lives in its five years. First the show was a web series, self-financed by married couple Sinclair and Katja Blichfeld; then it was part of Vimeo’s first foray into premium content. Then High Maintenance made the leap to full-blown HBO half-hour, growing in production budget, exposure, and run time.

In theory, the second season of the show’s HBO incarnation should make for a relatively stable transition, but the latest volume of High Maintenance, which premieres this Friday, has seen the most upheaval yet. Behind the scenes, Sinclair and Blichfeld ended their marriage while continuing to collaborate on the show—Blichfeld has since come out—and, for the first time ever, enlisted a writers’ room and outside directors. In the episodes themselves, you can feel that something’s changed: Some episodes are denser than ever, packed to the brim with overheard snippets of New York conversation; some are darker, including ones that delve into The Guy’s previously enigmatic personal life. (In an example of art anticipating life, last season’s finale revealed that The Guy lives down the hall from his ex-wife, who now lives with another woman. This season, we meet the ex-wife, played by well-known indie actress Kate Lyn Sheil, when The Guy gets in a bike accident and she cares for him in the hospital.)

“I don’t want to watch a show that doesn’t evolve. That’s not the experience I’m interested in,” Sinclair tells The Ringer about Season 2. High Maintenance remains one of television’s most empathetic, sharply observed, and silly—this is a show about getting stoned—comedies, but in its maturity, the show has begun to experiment with both tone and long-term narrative. In advance of the season premiere, Sinclair spoke at length about preserving the authenticity that gave High Maintenance its devoted cult following while branching out into bigger, more ambitious stories, and considering what comes next.

I saw from Instagram that you were just in Asia. I hope the jet lag isn’t too bad.

Oh, it’s insane.

Well, I appreciate you taking the time to talk with me anyway.

Happy to!

This is the first time you and Katja have brought on outside writers and formed a room. Can you talk about how you arrived at that decision?

Every year, we’ve doubled our workload, it seems. When we started the web series, we would release three short stories at a time. That was, like, six to 10 minutes each, so maybe a half an hour at a time every couple of months. Then we did the Vimeo season, and we kind of doubled that: six short stories at one time. Then we did the HBO first season, and we did six episodes, which each had two short stories. Except one had one, so it was 11 short stories that were released at one time. This time, we did 10 episodes. I wanted to make sure that the average was two stories, but some episodes had three short stories, and some had one long. I wanted to average about 20 to 25 short stories from those 10.

So we kept on doubling our workload, but shrinking the amount of time that we had to do it. And we had to work on them all at the same time. It was just like, “Are we crazy? Are we gonna burn ourselves out yet again?” Because the first season, I think we burned ourselves out. The writers were a necessary way for us to maximize our efficiency, but also to gather more points of view and perspective. First of all, we’re from a very specific Brooklyn subset, which is fine to talk about sometimes, but New York is full of so many different people that we wanted those points of view to be featured. I think that’s one of the reasons people like the show: It can be about anybody.

The second [reason] is, we were so busy working on the show all the time that we didn’t have much of an opportunity to go out and have our lives. [Laughs] We were running out of material from our lives to source from that wasn’t about working or the entertainment industry or being ambitious or this or that. We wanted to pull from the life experiences and points of view of these really talented writers and directors that we had assembled. We were very lucky in that everybody was so cool with our process, which was its own thing. It’s not like another TV show. It’s like a series of short stories, and it’s definitely its own thing.

Once you brought those writers on, how did they affect the show?

There was one writer who was more veteran who was really concerned with the arc of The Guy. That is not something that we had ever done, which is build a season-long arc. Most of the stories were very modular. I think that writer’s concern with our season structure as a whole really helped us a lot.

There were other things, just like jokes and dribs and drabs. At the end of the first episode, there’s a balloon that’s tossed back and forth by a kid on the subway. That’s a moment that was offered to us by one of our writers that he featured in his book that he observed on the subway in real life. I said, “You know, honestly what would be the best ending is that situation you described in your book,” and he said, “You can take it.”

His name’s Isaac Oliver; the veteran writer I mentioned before was Rebecca Drysdale, who has written on Baskets and Key & Peele and other things. Isaac’s a humorist and writer, and he wrote the book Intimacy Idiot. He performs at Joe’s Pub all the time. He’s wonderful.

The Guy’s arc is definitely something I wanted to ask about. I feel like in previous seasons, we’d learn about the unnamed catastrophe in the first episode from someone else, and then The Guy would come in. Instead, we learn about it from his point of view. The season as a whole felt more focused on him.

Just a little. Not too much, we hope. In the end, there are four episodes that deal with how he feels about things. In the end, you don’t really know much, except that he has an ex-wife, he went to a liberal arts school, and he’s got Jewish family members out in a suburb. But that’s pretty much all we know about him.

We also learn a little more emotionally.

Oh, definitely much more emotionally.

You know, a lot of people—and this comes with my perspective, personally—a lot of people want to project this sage, advice-giving Buddha atmosphere onto him. And while I think that The Guy, for me, is a representation of me at my best, I—because of my split with Katja, romantically, and dealing with the conditions of the world—I felt terrible for the first half of 2017. It didn’t feel good. I was in a period of mourning. I was also, even, almost starting to begin to resent the expectation that me, Ben Sinclair, was this character when I would be out on the street and someone would just want to say hi and expect that I was gonna be super-friendly and happy. I just wasn’t. I guess I took advantage of this platform that I had to exorcise some of that grieving.

Indeed, that was very much a large topic of this conversation: how much of The Guy we were going to use, because that wasn’t in the spirit of our show. It’s not what we did, we should just keep doing what we were doing, yadda yadda. But I think that the show has to evolve. I don’t want to watch a show that doesn’t evolve. That’s not the experience I’m interested in. I think it was all about the balance of how much more we could give him. The “twist” of this season is that the main character isn’t as happy as you thought he was, pretty much. The main character is just a human being. We went into that a little bit. Don’t get me wrong: I still want this to be a series built on modular short stories that can drop into anybody’s life. But, I don’t know, it felt like a departure for us and a risk to go into this character’s emotional life. We kind of commit to that in the very first scene, where we’re literally inside of his head in a dream. That’s kind of letting the viewer know: This is how some of this is going to be this season.

Having also been involved in a bike incident and hospitalized, I definitely found some of that vulnerability relatable. [Laughs]

Hannah Bos and Paul Thureen pitched that to us when we were looking for writers as a possible thing. I had always had, in the back of the mind, that The Guy would get into a bike accident, because that’s not an if-it-will-happen, that’s a when-it-will-happen situation. It’s a synchronicity that worked out really well. Katja got into a bike accident while filming the 10th episode in September. It was pretty much a flipped scenario that we had acted out as the first episode we shot, which was the hospital thing.

We really took a risk, to be honest. The reason why we’re stuck within those curtains is I thought it would be a production nightmare. [Laughs] To have an open, Nurse Jackie situation—I didn’t think we could pull it off with our budget, so we used voices and ADR, with the help of our DP and the incredible acting of Kate Lyn Sheil and all of the actors who contributed to that. That episode is very close to my heart.

You mention Kate Lyn Sheil, who’s one of a few more recognizable actors this season. Has your casting process changed with your profile and budget? How do you balance those cameos with preserving that anonymous New York feeling?

We want to work with people who want to be there, if that makes sense. Kate Lyn and Danielle and Yael Stone are all people who have first come to us and said, “I love your show. I’d love to work with you.” We’re looking for enthusiasm.

Also, there is that sweet spot in somebody’s career, which is not too big that they’ll be distracting, but big enough that they would be able to build their chops. They would have the experience of being on set and trying something new and understanding how a film set works. Peter Friedman, the guy who plays Jim in “Tick,” he’s a great example of an actor you see a lot, but you don’t necessarily know his name. Lee Tergesen, who plays Leo in the swingers episode last year, is another great one. He was in Wayne’s World, for crying out loud! He was in the car during “Bohemian Rhapsody,” and here he was on our show! It’s those familiar faces and just good chops. We’re looking for chops.

It has changed a little bit. Like I said, we’re always working on the show, so we have less time to go to theater and watch TV. I don’t really watch that much TV anymore. I would really love it if one of the executive producers was sitting in on the casting session. I would like to sit in a casting session, because at the end of the day, we’re going for a vibe, a feeling. Bunny Michael is a person who has a small part in the season who, just by using her, represents some sort of internet, meme, young person, gender 2.0 culture.

Last season, there was a concerted push to broaden the types of stories you guys were telling, and that effort seems to continue this season with stories about gentrification and visiting parents. How are you still changing the definition of what the show is?

When we put stories next to each other, we wanted to make sure that it didn’t look like the same types were next to each other. “Tick,” the episode [last season] with the Chinese can-collecting parents and then the bourgie ones, and the story [“Museebat”] with the Muslim girl living next to the swingers, I was trying to do artful contrast.

I think this season, we’re not trying so hard. We didn’t feel as much pressure to make this successful jump from web series to TV, and we were a little less self-conscious this season. We had all these ideas, and we would constantly revise and edit and change the order and put this story with this story and this and that, but we understood that it was all gonna work out in the end. [Laughs] And there’s a little more ease.

There’s a really kind review that Emily Nussbaum wrote about us this week [in The New Yorker], and she points out the bumpiness of Season 1. I’m so glad that she pointed it out, because I felt that way about it too. I was really proud of some of the moments we did, but as a whole, as a season with an arc, it was uneven, and the pace was somewhat—we didn’t get out of there quick enough sometimes. We let it linger on this fancy camera shot that we were like, “Oh wow, we finally got the ability to shoot this way! Let’s soak that up a little bit!” I think we learned this year to get out of there. The more mature decision was to be brief.

It sounds like you’re a little more comfortable with being a traditional TV show, even as you’re working with this unusual format.

I think that’s very much the case. The first day I got on our union set last year, I’ll be real: I freaked out. And then I wanted to go take a walk, because there were all these people in this apartment and I couldn’t go anywhere and there were people in every room, whereas when we started, it was like six people plus the actors in a room. There was so many more. I remember leaving the building, just wanting to take a walk, and then a PA said into a walkie-talkie, “Got eyes on Ben. Ben’s on the move.” I was like, “Oh my God. How am I gonna get used to this?” I just had to really accept in that moment that this was not going to be the same anymore.

But guess what? Nothing’s ever the same. The only constant is change, I think Oscar Wilde said, and it’s very true. I just got more comfortable with the idea that I wasn’t gonna personally email everybody and invite them to set, and some days I wouldn’t know everybody’s name because the crew would be changing and day players would be coming in and out. I just didn’t have enough time to do everything. There was more acceptance of that, and my role as someone who has to set the tone of the set experience, but not necessarily do everything.

I read that the last episode is designed to serve as a series finale if need be. Where are conversations at about the future of the show?

The conversation is that we don’t know until they tell us. HBO typically, I believe, lets a couple of episodes run before they do. Though sometimes they do it beforehand. It depends. They’ll do whatever they want.

I think all of us are unattached to whatever outcome. I know that I have ambition to create my own, individual artistic point of view and personality, and that is forming. Even as I do these interviews today, this is the first week I’ve ever done interviews without Katja in the three, four years we’ve doing press about this show together. Even that is, like, “Alright, this has been a pretty good day. It’s gonna work out.” Whatever’s gonna happen is gonna work out.

But for my money, I think that we have created a really, in my opinion, amazing structure of storytelling with great people who are invested in the project and a following who wants to see more. I have at least a couple more years in me to take this show—which, by the way, can be any story it wants to be. We can really tell almost any story. I am invested in keeping this boat afloat and using it as a platform from which to launch my own individual directing and writing career while also collaborating with people I know and trust.

Disclosure: HBO is an initial investor in The Ringer.