Sinclair and Blichfeld are the creators of “High Maintenance,” a brilliantly crafted, wholly original comedy that began its six-episode run on HBO last month. Sinclair also appears in the series, playing a weed delivery guy referred to simply as “the Guy,” who bikes to the homes of a parade of eccentric New Yorkers. The Guy has a kind of omniscient passport into the inner lives of the lonely, yearning, lost and downright looney people every New Yorker will recognize; if not from the subway, then from the mirror.
The first episodes ran independently on Vimeo, where it quickly gained an audience based solely on word of mouth and critical acclaim. Vimeo then financed a second round of production, and the third installment is now on HBO. The human storytelling and romantic New York visuals remain consistent from those first short episodes to the longer ones of Season 3. IndieWire spoke to Sinclair and Blichfeld about their unconventional casting process, transferring the tone of the show to HBO and writing with the element of surprise.
I was warned not to reveal any of the episode’s twists, and I hadn’t thought of this, but it struck me that every story in “High Maintenance” upends expectations.
Ben Sinclair: Surprise is — a lot of it is just trying to wind the viewer up a certain way and then snap it. A slow reveal of what is actually going on with this person. We’d like for a change to happen within the viewer at some point.
Katja Blichfeld: We like when your allegiance changes. When you watch the scene and you’re like, “Oh, I know how this is gonna go, and then you’re like, “Oh wait, that person was the crazy one.” We like those reversals of allegiance.
Sinclair: In this first HBO season, the challenge was to balance 11 short stories while also keeping it fresh for today, for this week. And our editing process took a long time because we were constantly like, “we can make this even more up to date than when it was shot.” There was a little bit of tweaking throughout. Just to try to keep these fucking secrets a secret and try to keep it a gentle surprise.
With this HBO deal, “High Maintenance” is arguably the most successful web series of all time–
Blichfeld: Well, “Broad City” might take home the trophy for that one. They’re one of my biggest inspirations to get into this racket. I met [Abbi Jacobson and Ilana Glazer] as a casting director before we even released our first episode. I remember seeing them talk at a Writer’s Guild new media conference or something, and they were in the middle of their FX deal at the time, and they were super excited and having this moment. I was taking note of what was happening to them. They did a good job of doing something with a unique voice. It wasn’t like everything else, it just felt like that was their point of view, their tone, and it felt very New York. They told little New York stories. I remember we sent them our first trailer and asked for their advice. They were blazing the path ahead of us, and made me feel like we could keep going. [Ilana’s brother] Eliot Glazer is actually the first person who featured us.
Your origin story is so interesting, as a casting director [Blichfeld] and an actor [Sinclair]. I think that’s very encouraging for aspiring creators who may feel stuck in some other part of the industry.
Blichfeld: I’ve met so many casting directors who want to go into producing, and so many actors who go into producing and directing. As an actor, you want to have agency over how you’re portrayed. Ben taught himself to edit — when I met him, he had just spent the last couple of years nailing down that skill, and he was starting to make little commercials. I don’t think he even knew what he was doing with any of that. He was just passing the time and trying to make money.
Sinclair: Actors want agency over themselves. The sickening thing of web series is they can be vanity projects, and it can get very ugly when it’s done ungracefully. The temptation is to make a show where I’m the main character every week, and you’re gonna follow me, and you’re gonna fall in love with me as an actor. It’s hard to have restraint. Katja really led the charge of being like, “good things happen to people who are focusing on others, who are trying to lift other people up.” It was her impulse to be like, “we know all of these wonderful actors, why don’t we let these actors be themselves? And you be yourself, but yourself is in service of these people.” That was the key difference; we were focusing on the project more than our careers. We weren’t trying to get a TV deal. That’s the long and the short of it. That didn’t happen until we just made a whole bunch. A huge part of why it worked is because there was no end game in the beginning.
One of the show’s greatest strengths is its casting. You feature so many great New York actors, people one might not normally see on television. Is it harder or easier to write for specific people?
Sinclair: Depends on the person. Max Jenkins (a professional scene-stealer who plays one half of the duo saved in the Guy’s phone as “Assholes”), he’s like our weird little muse. We could write anything for him. But a lot of these people we know well, and they have strong voices. In the beginning, it was easy to write for people. It’s gotten harder recently, because now we’ve written for all the people we know. So it’s becoming more of like, write the character you wanna see and go through the normal casting process.
Has that been challenging?
Sinclair: We found out that we don’t like watching people audition with our lines. That does not work. It’s an awkward situation, to be reading our lines and to be proving yourself to somebody and trying to get a job. It’s not a way we like to watch our actors behave. We’re not there, we can’t feel how they’re feeling us. Because we were writing and directing and doing five jobs still on this incarnation, we didn’t have the luxury of having the time to go to casting sessions.
Blichfeld: Our casting director put people on tape, but, like Ben said, it’s a little awkward for us hearing our words read back. It felt stilted and strange with us not being there. So we were like “just interview people, just chat with them so we get their flavor on tape.” They would just have a conversation on tape — the casting director [Christine Kromer] would just be like, “tell me what you’ve been up to.”
The second episode, “Museebat,” follows a Pakistani-American teenager living in Brooklyn. It’s so refreshing to see a Muslim character on television who isn’t a terrorist. What inspired that?
Blichfeld: We were living in Boerum Hill at the time, where Muslims are everywhere. Why don’t we ever see Muslim characters? We know people who don’t practice, but they’re culturally Muslim. Not everybody’s religious, it’s not always the main thing dictating their life. So we originally wrote it as a Muslim girl, but we were like, “she could be an African Muslim, she could be a Pakistani Muslim,” and we let casting show us a variety of people. We cast Eesha (Shazi Raja), and then we cast the family around her. Even then, she’s from Houston, so she didn’t feel like some true blue New Yorker, and we weren’t even going to try to pretend that. But we liked her, so we were just like, “tell us your experience of having family members living in Houston,” and peppered the story with little weird details from her life.
You had the script, but you were tweaking.
Sinclair: That one, up to the day we were shooting we were like, “this could feel more authentic.” Up to the day we shot, that one was up for grabs.
Blichfeld: We definitely had some cast collaboration on the show.
Sinclair: Every script is different. No draft is the final edit. The final draft of the script is when we turn in the episode.
Blichfeld: Then others feel like they’re to the letter. It’s whatever it wants to be.
Sinclair: These things are living, breathing things until they get turned in. And then I never want to watch them again.