The Guy is finally back on HBO, still dealing weed to the colorful cast of characters that make up the High Maintenance universe.
As the series keeps transforming, the show continues to deliver original vignettes of New York City and the fascinating humans that call it home. EW talked to co-creators and executive producers Katja Blichfeld and Ben Sinclair (who also plays The Guy), plus executive producer Russell Gregory about teaming up with This American Life in the premiere, and the joy they find in choosing which actors— sometimes recognizable from the show itself or elsewhere — lead their stories.
See an exclusive image of next week’s episode below. High Maintenance airs Fridays at 11 p.m. ET on HBO.
ENTERTAINMENT WEEKLY: To start, I always feel like this is a show that people can jump right into. Would you all say that’s still the case this season.
KATJA BLICHFELD: Oh sure. I still like to think of this show as something of a procedural.
BEN SINCLAIR: This season, the mantra was back to basics, and our basics were creating snackable stories that you could just jump into at any point and not need to be following an entire arc. So we were just trying to go back to telling stories of unusual people — that actually end up being the most normal people of all because everyone’s kind of unusual it turns out.
So what’s new this season? Are there storylines you’re excited about, or characters you can’t wait for people to see?
SINCLAIR: Gosh, there’s so many. I really think that the second episode “Trick,” is fantastic. It features Avery Monsen and Abigail Bengson. Avery is a friend of mine actually from Oberlin College.
RUSSELL GREGORY: Avery [who plays van Waxman, the asexual magician] is one of our most recurring characters on High Maintenance from the web series to now. There are a lot of returning characters this season. Going back to basics also meant we brought back a lot of our favorite and fan favorite characters.
SINCLAIR: Becca Blackwell also is coming up in an episode. They were in [a Season 3] episode called “Dongle.” Becca really impressed everybody with their just solid beginning to end acting. This show is so fun to work [on] because the people who we tend to work with are very ambitious, hardworking, and often they’ve been doing their own thing. It’s not like we discovered these people, but they definitely haven’t had a television show surrounding their character’s journey, and it’s so cool to see someone get so excited about that, like Abigail Bengson who’s in “Trick,” this is her first thing on TV. It’s such a joy to give the focus to somebody who’s been working their ass off for it for years.
BLICHFELD: I’m always excited by casting “weirdo” comedians and letting them show off their acting chops. In particular, Edy Modica, Ruby McCollister, and Rachel Kaly give really lived-in performances this season that I’m really proud to showcase. Not to mention, Russell. He’s a f—ing natural!
How do you all decide when to bring back a character, and has that process changed?
BLICHFELD: We’ve got a wall full of faces in our writers room. Literally. A couple of years ago, we decided to print out photos of all of our episode leads from our web series to present. Plus any characters we felt a special connection to, or just liked working with. While we were breaking story, we’d just stare at all these faces and they’d inspire us. Sure, it’s changed a bit since the old days when we just cast our friends or people who reached out to us.
SINCLAIR: [With the wall], you can kind of see how this referral system works within the community. Sometimes we’ll have a story or a situation [that] could be anybody. Why don’t we see who it might be who we already know because no one orders weed just once, these are returning customers a lot of times. So we use that practicality of buying weed to re-include the community that we’re building here.
GREGORY: At the top of the writing period also Katja, Ben and I do meet up, and we’re like, “Hey, who do you want to see? Is there anybody you’ve been thinking about?” We brainstorm ahead of time too. Usually the person that everybody wants to see the most ends up somehow not getting a story. It cancels out the most popular person sometimes because they’re either not available, or we just can’t find the right match. And then, sometimes they’ll write something that doesn’t have a character attached and our casting director Andrew Femenella will be like, “What about this person from the web series?”
SINCLAIR: Yeah that happened a lot this year.
GREGORY: In episode three this season, the [protagonist] Keesha was actually in an episode with Avery.
SINCLAIR: It’s just like having a reunion on set, getting a person back who has taken their experience from our show, gotten some more jobs from that experience with our show, and then is coming back and feeling like not only do they belong here, but their tested, and truly a part of this little community we made. It’s so nice. We’re essentially making two pilot episodes per episode of our show, we’re always restarting from the beginning. Here’s a character, here’s their world, here’s their situation, here’s why you should love them. We do that two times an episode, sometimes more, so it would be a dream come true to see those characters or those connections put into a new work of art altogether.
How does a guest like Larry Owens come on the show versus a guest like Nick Kroll? Is there a wishlist of people? Are people auditioning?
BLICHFELD: Larry is someone I saw at Caroline’s a couple of years back and fell in love with, then saw in [2019 Off Broadway musical] A Strange Loop and pretty much lost my mind. We all did. That guy is the total package. He feels like he can do anything.
SINCLAIR: I was writing that episode and we’d already been talking about Larry for that part, but I had only seen his YouTube stuff, so I went to see A Strange Loop, and went up to him afterwards and said “We’re going to ask you next week if you want to be in the show,” and he was like, “Great.” That was like an on the spot, “Nice to meet you, can’t wait to work with you,” and a gracious acceptance.
BLICHFELD: Nick Kroll is a good example of someone who’s a star, but also a friend of the show. It felt so nice and comfy to bring him aboard. I’ve known since my earliest days in New York when I was a baby casting assistant scouting talent in the UCB basement, so it felt like a full circle moment for me, personally.
SINCLAIR: Nick wrote an email to us a couple of years ago, when, when he was doing Oh Hello [on Broadway], he had just found our show and we had some mutual friends, and [so] Nick’s a friend now. I texted him because we were doing these scenes with actors, and usually when we work with recognizable faces, we put them as actors in the show. We’ve done that with Jemima Kirke and Hannibal Burress. Those situations too were those actors emailing us first, being like “Hey, like your stuff,” and then when the opportunity comes along, to their agents chagrin we contact them directly and say “Hey, you’re up if you want it.” Rebecca Hall is the same. We are friends with Rebecca Hall through Dan Stevens, and they are good friends from school, and Dan Stevens [is] another person who reached out to us through Facebook. Casting is [equal parts] the collision between a personal relationship and an admiration for their craft.
BLICHFELD: It has to make sense. We’re not chasing eyeballs, so we’re not chasing stars.
GREGORY: And then sometimes, when we don’t have the answer right at our fingers, Andrew comes into play.
SINCLAIR: And brings us someone none of us could have ever imagined. Because Andrew is such a guy who’s so diligent at attending things, and seeing who’s who, and knowing what they’re working on. His memory is absolutely encyclopedic.
GREGORY: And understanding Katja and Ben’s taste, that really is key.
SINCLAIR: For the first episode, to cast the parts of Yara and Owen, that could have gone so many ways, and we got a lot of talented actors in there. And I remember just going up to Andrew and being like, “Andrew, what do I do?” And I was like, “Who is it?” And he goes “Well, this would be the more interesting choice based on what people usually see on TV.” And he was right.
It was surprising seeing the This American Life staff, more than just Ira Glass, make a cameo. How was working with them?
SINCLAIR: The This American Life folks are such consummate professionals in telling stories, but to put them in the room and hear their familiar voice that we hear on the radio, not just into the microphone, but bouncing off a wall, and clamoring to speak like normal human beings, vocal fry and all. It that was such an exciting moment for all of us because naturally we respect that show so much, but also I felt like I’ve been learning from them for so long. To see them be like, “Oh, so this is how you make a TV show. I had no idea.” It was absolutely surreal.
This interview has been edited and condensed.