It sometimes feels like a miracle that there is a television show that airs on HBO that isn't about dragons or polar bears with armor, that doesn't remix a comic book classic or star a comedy legend, and that isn't obsessed with the lives of the obscenely wealthy. But for the last couple of years, High Maintenance has thrived under-the-radar as one of the most intimate, empathetic programs on TV. It's a Gothamist favorite, a wide-reaching portrait of living in NYC today that is successful because it is familiar without being rote—as if you set up a camera in your own cramped apartment then passed it to your neighbor.
The show is returning for its fourth season on HBO on Friday at 11 p.m., and in anticipation, we spoke to co-creators Katja Blichfeld and Ben Sinclair (who also plays The Guy), as well as executive producer Russell Gregory, to learn about how different making the show is now compared to the web series days; talk about the evolution of the storytelling; how they ended up collaborating with Ira Glass on the new season; and the concept of "aspirational kindness."
How different is making the show now in season four compared to the pre-HBO days?
Ben Sinclair: It's day and night. It is like a summer day and a winter night. [Laughs] We like constraints, and I will say that there were some constraints that seemed mammoth in the web series days that we bounced against, and there are different constraints in making it in season four which feel just as insurmountable and momentous as they did for the web series. So the elements that make creativity roll along and hum are all there. They're just different elements.
For instance, we like making nine episodes at a time each which have at least two stories in them. So focusing on 18 to 21 short stories for nine months out of the year and multitasking from story to story is way different than taking one short story at a time and taking one weekend to shoot it and then taking the rest of the month to edit that and then doing all of the editing and sound mixing yourself. It's totally different, because now we have a crew of over a hundred people, I believe. What's happened that is probably the most gratifying is we've created a little community around this show. People come and go, and it is added to and taken away from. But I think we really leaned into the community this season, and I think this season is better because of it, because we've allowed the community to have more ownership over the project and we all have it together.
That was something I really picked up on when I visited last year—how many people had been working on the show across different departments for a long time, how much continuity there was as a result, and how much they felt personally involved in the show and saw themselves reflected in different ways.
Ben Sinclair: Oh yeah, dude. I remember in 2011, in Katya and mine's apartment, [we would] talk about wanting to build an artistic community based around one project that could involve different jobs, different directors, different writers, different groups. That was part of the initial goal of the whole enterprise. So to see it in fruition, and then maturing, is really exciting. I would say there are some people on this set who have become very, very, very good friends.
Katja Blichfeld: Russell's the godfather of one of our producer/cinematographer's kids, and [the couple] met on this show.
Ben Sinclair: And one of our camera people has become a writer of our show. It is truly an all-in affair.
Russell Gregory: One of our DPs is a producer. I'm everyone's emergency contact, which is a terrifying thing nowadays. [Laughs]
Katja Blichfeld: But very real.
Larry Owens
I think a lot of people don't necessarily understand what the role of an executive producer really is, and how crucial Russell's contributions are to the show. I was wondering if you could talk a bit about the various kinds of jobs you end up doing, and how your role has shifted between the pre-HBO days and now?
Russell Gregory: The title executive producer is sort of nebulous because executive producers can have varying degrees of involvement. For me, because I was with Katja and Ben since the beginning, I have a very hands on role. Along with the two of them, I weigh in on all the final decisions that go into making the show. This is similar to how it was in the web series, but on a much larger scale. During the web series, there were a handful of us doing everything ourselves. I would find myself coming up with stories and situations, making budgets, tracking down locations, crafting props, casting, 2AD-ing, catering, finding wardrobe, casting extras, and even doing the job of a PA at times.
As we moved to HBO, we obviously got a whole crew of very talented people doing these jobs. So instead of doing all these things myself, I get to help all these departments achieve Katja’s and Ben’s vision for the show. It means year-round involvement in the show: not just during production, but the writing period, pre-production, post and final press.
During production, I try to be present on set as much as possible. This became especially true once Katja and Ben started directing separately, and I became the one of the three of us who was on set everyday. My goal was not only to help establish consistency to what went on camera, but also to keep the vibe on set our traditional High Maintenance feel and check in with as many people as I could. Humanity in front of the camera starts with humanity behind it. I try to watch, respond, laugh, cry, get insulted or overcome with happiness. I love being on set and watching everyone do their work. It’s almost overwhelming sometimes to think of how hard everyone works to bring these worlds to life.
What has surprised all of you about the way the show has evolved over the years? Did you ever think you would really dive into the backstory of The Guy in the way that you now have?
Ben Sinclair: Not really. I think we've taken this project one day at a time, one story at a time. We did have [thoughts like], "Oh, wouldn't it be cool if..." or "We should hold off this until...," et cetera. At the beginning of every season, there's a little bit of a data dump, we'll call it, of what's going on in our minds. We'll just have a long hour and a half conversation about what's humming along in our brains. And we'll start the writing process, we'll start the production process, and then we'll come back to that. It's funny to come back to the notes of that conversation at the end of the year and it's like, oh yes, we executed whatever was fumbling around in our brains in April of the year before. So it is kind of a year-to-year evolution.
Katja Blichfeld: And we don't plan that far out what we're going to do really. It's as you said, we didn't really know we were going to have the longevity that we've had, and I don't think we accounted for it. We haven't sat down and mapped out The Guy's arc over many seasons, it doesn't work that way. It's sort of a conversation that's had at the top of the season where we're like, what's going on for this character? How do we want to represent that? How much or how little do we want to see him? And then kind of go from there.
Ben Sinclair: I do think though in this season premiere, that Ira Glass monologue at the end where he's talking about looking around in the trash and looking for what's good and reusing things—I do feel this season has a theme of reuse, coming back around, and time passing and things reincarnating into different forms. I really do think that is the thesis of this season.
Russell Gregory: We did want to get back to a lot of the elements of the web series, so that plays into that as well.
Ben Sinclair: Yeah, it is. We are kind of reincarnating every year and everything is a cycle.
Something that came up last season was that Ben said he felt that season three wasn't necessarily the best of the show: "This isn’t our best work...I’m feeling comfortable about not always hitting it out of the park, and [that] some episodes are stronger than others." And I was wondering, for all three of you, what differentiates a successful or great episode of High Maintenance from one that is merely okay?
Ben Sinclair: Well, I will add an addendum that since I said that, many people have come up and said that season three was what they considered a very good and successful season. [Laughs] I think that statement was [an attempt to] practice non-attachment. Sometimes an episode we work really hard on, we call it a "problem child" episode and it takes five times as much more work as the other episodes, and at the end of all that work, it feels just as good as an episode that we kind of shat out really fast and everything falls into place really quickly. It was an effort to say you can't win them all, and it's important to just keep on going when you're on a TV show because there's so much work to do, there's not enough time to do it. You've got to move. You have to move ahead and not flog yourself for not always doing work that made the goal.
Katja Blichfeld: Yeah, and I think we also have an awareness of what it feels like to feel really inspired, and have that inspiration translate into an episode that comes together really seamlessly. When this was a web series, we were doing it at our leisure. So production happened when inspiration struck us, and when we had access to all the ingredients so to speak—when we had an actor and a location and all of those things. And we got to experience what it felt like on a number of occasions: to have all the elements come together just right, to have the alchemy just sort of happen and work in this way that is guided by just pure inspiration and creativity, and is free from any sort of contract or deadline or compensation.
It was our art project once upon a time, and that is going to feel and look very different day-to-day from what it is now, which is our job, so to speak. A job we like very much, and get a lot of creative fulfillment from. So sometimes we're able to duplicate that or replicate that process when all the elements line up just right, and the idea flows and we get the perfect cast attached and the access to a great location and so on. But there are other times when the process feels a little more labored because, oh no, we only have a week to prep this and, shit, we don't have this thing that we wrote into the script and, ah, now what do we do? And then time and energy gets eaten up trying to solve an issue. And sometimes those episodes do turn out great, but really by and large, the best ones are the ones that come together pretty seamlessly on the initial part of the process, I think.
Ben Sinclair: I would describe our journey as a spiral. You're moving in a circle, but you're ascending or you're falling. So you're coming around to the same part of the circle, but you're at a different vantage point.
Katja Blichfeld: Oh, my therapist just said that last week. [Laughs]
Ben Sinclair: But yeah, we're in an upward spiral.
If someone was like, "I've never seen High Maintenance before, what's the deal with it?", are there any episodes you would point them to in particular to say, "this is what we are trying to do, this is what we're about."
Ben Sinclair: It's fun to start from the web series, the first episode "Stevie." As much fun as the episodes themselves are to watch, it's fun to watch us figure out the show as we move along, and it's fun to watch our own personal lives seep into the episodes as you watch through the series. It's a mom and pop shop, and a fun part of the web series actually is that it just came out of nowhere. It didn't have some Deadline article attached to it. It just sprang from the universe spontaneously, and I think that's one of the things that people like about the web series. So I would recommend—Ben, tell people to go to the series page on HBO.com, go to High Maintenance, next to that it says High Maintenance web series. All of the web series episodes exists on that page. Make this search engine optimized, because it is important that people know that the web series is on HBO and they should start with the "Stevie" episode of the web series and keep watching. [Laughs]
Katja Blichfeld: When someone hasn't seen it, I kind of tailor my recommendation to what I think they might enjoy or relate to the most, to be honest, which is different for every person. What I would recommend to my parents' friends is not what I'm necessarily going to recommend to my new friend that I meet at a party.
Ben Sinclair: I'll also say that the season one HBO premiere called "Meth(od)" was not intended to be the first episode. [Laughs] I think it was actually kind of a strange choice to make that the first episode of our HBO series. So...maybe don't start with that one.
Katja Blichfeld: I never tell people to start with that one.
Ben Sinclair: It's a good episode. I like it for its own reasons. But it's not a good first episode. My bad.
What was supposed to be the first episode of that season?
Ben Sinclair: "Tick" was supposed to be the first episode. The one about the collectors and the daughter and the father, that was supposed to be the first.
Ira Glass
For the new season, how did the collaboration with This American Life happen? It's a little different set-up than the usual kind of cameos or guest stars that you've had.
Ben Sinclair: In December of 2018, I said to myself, "Self, we're going to have an episode with This American Life." I found a note recently that said, "This American Life: we're going to get involved." And yeah, within a couple of months, Ira and I were friends. Ira was a really good collaborator on that episode. I would send him a draft and he would be like, "This would happen in our office. This wouldn't happen in our office." And that's how it came to be. They are kind of an "indielectual" analogue, as our marketing at HBO would like us to call out the "indielectual" crowd. [Laughs] We both tell stories. We're both anthology series. We both have a sensitivity, and it doesn't seem like either of us are into sports, and it seems we were mutual fans of one another. It seemed like a good fit.
The premiere also features comedian Larry Owens, who is hilarious as a singing telegram. With someone like that, are you saying before hand, "we want to work with this person and write to their strengths"? Or do you write it and then cast it afterwards?
Ben Sinclair: That episode in particular was tricky because it went through so many iterations, but Russell Gregory has had the singing telegram experience from his past life in Florida. And everyone was going to see A Strange Loop at that time—I hadn't seen Larry performing live, but I checked out his character reels on YouTube, which are insanely funny, and I saw Strange Loop...
Katja Blichfeld: Yeah, he's been kicking around for a while. I had seen him the previous year, but he was one of those people everybody was mentioning, and then Strange Loop really just made it a no brainer. We all saw that and we were like, it's him, right?
Ben Sinclair: His dancing really sealed the deal for me because of the ballet sequence that the episode eventually gets to. We were looking for a mover.
Russell, can you tell us a bit about your days as a singing telegram?
Russell Gregory: I worked as a singing telegram in the late '80s for a company in Tallahassee, Florida. I was a theatre student at the time, and working a few part time jobs, so I thought this was a great way to perform and earn money. Most of them were pretty normal, singing a retirement song dressed as a bellhop or a birthday song dressed a gorilla in a tutu. But this company also sent out “stripper grams”—they only stripped down to bathing suits—and part of that package was you got some balloons and a singing telegram as a pre-show warm up. I was paired with the female dancer which meant I ended up singing the “Marriage Marriage” song to a room full of drunk, north Floridian males, all waiting for a dancer. I was basically a gay joke for a few minutes for tips. Obviously, I didn’t get many on those jobs. Thankfully, the dancer I was paired with had that great work ethic, made great tips, and always split them with me.
This one is a little more for Ben: how much of you is in The Guy? In what ways are you most similar and where do you diverge?
Ben Sinclair: I think I'm a little more tortured than The Guy. I have a little more angst and even anger than The Guy. And I'm a little more aspirational than The Guy. I'm a little more tied to desire and want in a way. I'm more imperfect than he is. He's not perfect at all by any stretch, but I think he's got a lot more patience than I do. And I think he's more forgiving of himself and others than I am. I basically just said a bunch of bad shit about myself, but that kind of cops to my biggest aspiration, which is to be more like him.
There is an aspirational kindness that seems to hover around him, like a halo.
Ben Sinclair: Yes, and I think that, it depends on who you speak to, but some people would say I am good but with a very present dark side. And I think his dark side is a little less present.
Russell Gregory: I think we all think that we're a little bit of The Guy, also.
Ben Sinclair: Working with Russell and Katja and all the other people who I'm surrounded with, they are a lot of the reason why The Guy is so aspirationally kind. It is their input and it is their north star that is a really big help into making him a person that people want to be around.
For him to continue to act as this conduit to other people's lives, does that prevent him from growing himself?
Ben Sinclair: I would say "man explores" is the headline of that character. He's just "man explores." We gave him a little bit more backstory in seasons two and three on HBO, and this season we kind of lay off of that a little bit. We pepper in some of his journey in the background. I do think that he has been searching for community for years, and he's a person who's in and out of things. There's a lot of talk about intimacy this year. In HBO seasons two and three, and even one, The Guy had a thing with relationship stuff, and this season there's a dog, which is a different kind of relationship. With him, it's always "man explores." He's kind of trying to find the meaning of life, but also understanding that maybe there is no meaning and that's okay.
Thank you so much for talking to me. My last question is a silly one: have any of you ever gotten too stoned, and what's the most memorable thing that happened?
Katja Blichfeld: Oh, of course.
Ben Sinclair: I've been too stoned for 10 years, man. [Laughs] No, actually I have not been smoking very much for the past month, and when I get stoned now, it's a real ride man. It takes me really one hit to get blasted. And I actually appreciate the ability to get too stoned these days, because for a while I was just chugging weed and I couldn't get stoned enough. So it's a paradox in that way.
Russell Gregory: I will also say there are people who get too stoned around us.
Katja Blichfeld: Yeah, that happens more. I think over the years we've noticed people try to keep pace with us at social gatherings when we are smoking, and we've watched a lot of people go down at a party. [Laughs] That's more what we see than us getting too stoned. I haven't been that brand of stoned for over a decade.
Russell Gregory: We're still functional stoners over here.
