How High Maintenance Found Itself in Conversation With This American Life

As High Maintenance enters its eighth year of existence, the web series turned HBO anthology faces the hazards any long-running creative project inevitably encounters, primarily the potential for stagnancy. Even correcting for the flexibility of its format — each episode follows the lives of different New Yorkers who all buy from the same nameless weed delivery guy — High Maintenance has a specific tone and structure that could easily devolve into self-parody.

In a recent New York Times Magazine article, writer Willy Staley criticized High Maintenance’s pattern of introducing characters in a distinct light before revealing significant details that purposefully color the audience’s initial perception of them. Characters outside of a certain professional and class status are “often made relatable to HBO’s audience by being supplied with some quirk, hidden talent or non­-normative sexuality,” writes Staley, asserting that “the show depends on its audience’s prejudices in order to undercut them.”

Any TV show that has produced as many episodes as High Maintenance risks falling into these types of prescribed formulas and narrative shortcuts, even if it’s not calculated on the writers’ part. And one way to break out of this mold is to examine the process itself, either by foregrounding it or unpacking its execution, which is what High Maintenance did with last week’s premiere of the show’s fourth season on HBO.

In “Cycles,” creators Ben Sinclair and Katja Blichfeld interrogate their own show’s creative engines by partially setting the episode in the offices of another long-running anthology series: This American Life, the popular nonfiction radio show and podcast hosted by public-radio veteran Ira Glass. Sinclair, who wrote and directed the premiere, had wanted to do a High Maintenance episode about This American Life for a while, not just because he was a fan of the program but also because the shows share a worldview that allowed him to explore his own creative process.

Glass, who had been a fan of High Maintenance since its web-series days, also felt a connection to the show’s point of view. “We look for stories with characters and scenes and a story arc, and so do they,” Glass explains. “It seemed like their basic mission was in the general neighborhood that we were in, even though they’re using the tools of fiction and we’re using the tools of fact.”

Sinclair met Glass at a This American Life Christmas party and they became fast friends. Eventually, they began to work together to figure out what an episode involving This American Life offices would look like and how it could potentially shine a light on the High Maintenance production process.

It’s understandable that Sinclair feels an affinity with This American Life. Both shows hew to an anthology format and share a comparable humanist outlook, two qualities that facilitate a sense of durability, but also the potential to conform to predictable rhythms. As This American Life enters its 25th year of being on the air, Glass and his staff are hyperconscious of how their show can fall into various pitfalls and repetitive traps. Nonetheless, they’re eager to break certain patterns in order to stay modern and stave off repetition.

“When people pitch stuff, we often say, ‘We can’t do that; that’s too on the nose,’ or ‘That’s too in the style of the show in 2003 or 1997.’ All of us agree that the show feels the best when we’re doing something that we’ve never done before. A lot of energy goes into trying to find stuff like that and nudging the format this way and that and trying things. We’re acutely aware of our own show.” 

Blichfeld confirms that they confront similar issues in the High Maintenance writers’ room. She notes that their team is mindful of being too preachy or too obvious or too heavy-handed with certain themes, and that they get the best results when they stay loose and instinctual.

Accordingly, “Cycles” went through many different versions before landing on the one that went to air. It initially was going to be an episode about being a workaholic that followed Glass as he endures a particularly stressful day. Sinclair also batted around a version of the story that followed the This American Life staff as they scrambled to put together an episode of their show. It eventually morphed into a story about, as Sinclair puts it, “how stories get told when you have to do it on demand week after week, which is what we’ve been doing for almost ten years.”

For “Cycles,” Sinclair took inspiration from a story his friend and This American Life producer Elna Baker told on the show about her own experience with dramatic weight loss. In the episode “Tell Me I’m Fat,” Baker talks with her husband, Mark, about her existential crisis regarding her appearance, openly wondering if she could have attained the same opportunities in love and life if she stayed fat. In the middle of her interview, Mark admits that they probably wouldn’t have ended up married if he had met her when she was 100 pounds heavier.

“It’s such a hurtful thing to hear,” Glass notes, “and they kind of work it out on tape, and [Ben] was just very interested in that as a thing to make drama from. It seemed inherently powerful and very specific to people making podcasts.” 

Baker’s story becomes grist for the A plot in “Cycles,” which follows a fictional This American Life staffer, Yara (Natalie Woolams-Torres), who struggles with her very first radio piece. Yara’s story for the show initially follows her parents’ own tumultuous relationship: They were planning to get divorced when Yara was a senior in high school and decided not to tell her about it, but when her father fell off the top of her school’s bleachers and survived, her mother committed to helping him through the recovery and they fell back in love again. It’s a compelling narrative — the only problem is that neither of Yara’s parents is interested in speaking on the record.

While working through the roadblocks in her piece, Yara celebrates her anniversary with her boyfriend, Owen (Marcus Raye Pérez). They get stoned together and she soon starts free-associating on tape about topics surrounding her piece: womanhood, gender roles, and how her mother’s choices in life were inevitably circumscribed by societal expectations. She eventually says that she admires how Owen’s ambitions are smaller than hers because it means that he would never impede her own professional goals. This sparks a devastating argument between the two of them that’s all captured on tape, which Yara later brings in to work to receive notes from the staff. 

Sinclair saw Baker’s story, and how it’s reflected through Yara’s, as a reflection of his own diarist impulses. He frequently uses scenes from his own life as inspiration for High Maintenance episodes, and he saw an affinity between his practice and the one used to create radio journalism. “Elna helped clarify for me what it felt like to so personally unpack your own life situations into that radio format,” Sinclair notes. “They’re journalists, they’re recording this stuff and using that as their primary source. We’re making up fake shit and taking truth to re-create it. The little differences in it were filled out by Ira and Elna, but it pretty much is the same process.”

Glass, however, has a different view of their method. He says the main point of comparison between his show and Sinclair’s involves the chaos of trying to find a story to tell. “When we’re putting together a story,” he says, “we’ll wander around and interview lots of people and try to find the most interesting part of the story. [Ben] pitched and even wrote a bunch of versions of scripts and would show them to me and ask, ‘Does this make sense?’ The inefficiency on the front end, that part was exactly the same.” 

But the similarities mostly end there. There’s a strict procedure to producing and recording even the most personal This American Life stories that High Maintenance doesn’t explore. For one thing, pitches of that nature undergo a stringent vetting process. Glass insists that the story Yara pitched in “Cycles” would never have been green-lit on the spot because it seems so superficially unbelievable. “Some people on staff were like, ‘Wait a second, her dad fell off a bleacher and lived? Is that a true story? Where is the level of skepticism that we would actually bring to these pitches?’”

Glass concedes that critical nature had to be elided in order to get through certain plot points. Still, he and the staff had strong reactions to Yara’s journalistic practices. When I initially spoke to Glass, neither he nor the staff had seen the episode yet, but they were screening it later that evening. After they watched it, he called me back to express the staff’s criticism of how their process was depicted. 

“They were sort of horrified by the plot with the fictional staffer who’s recording her conversation with her boyfriend while stoned,” Glass said. “The thought that that’s what journalists do, or what we do, seemed just deeply wrong to them. It’s true that this story line was based on something that Elna Baker recorded for an episode of our show, but that was a conversation that she sat down to do, not while stoned, as part of a story with a plot and some points to make. There’s no story in the history of this show where it’s just people pulling out tape recorders in random personal situations. We’re doing actual reporting, even if it’s on personal stories.” 

He also stresses that no one would actually bring in a tape of a stoned conversation for staff review. “They might play it for their editor to be like, ‘Is there anything here?’ and the editor would be like, ‘No, there’s nothing here.’ They wouldn’t assemble six people in a room. That part of it seemed very much of an outsider’s view of what it would be like to do a podcast.” 

With that said, Glass says that everybody mostly enjoyed the episode, and that Sinclair broadly captured the feeling of being in pitch meetings and edit sessions on This American Life. (He also says that Sinclair and D.P. Ashley Conner photographed the staff in an aesthetically pleasing light: “They lit us very beautifully. Everybody looked great.”) Though it might not be an entirely accurate depiction of what it’s like to work at This American Life, “Cycles” nevertheless depicts the radio show as a well-oiled machine, one that operates efficiently but requires a lot of supervision and hands-on engagement.

With its relatively modest budget and fine-tuned production process, High Maintenance is in a position to develop into a long-term project much like This American Life, leading both Sinclair and Blichfeld to ponder the future of the series and how it could possibly continue on for years to come.

“This show could conceivably go on forever, be it with me and Ben at the helm or others,” Blichfeld says. “There are so many people in our tight-knit group that get the show in a really special way and have internalized its ethos … it does give me that feeling that it could go on for longer than maybe I would have thought a few years ago when we first made the move to television.” 

Sinclair has more conflicted feelings about High Maintenance’s future, or at least his involvement in it. “Is there a situation in which I want to be doing this show for 20 years, and for each of those 20 years it’s a ten-month-long job?” he wonders. “I probably want a little more time to just go be a human being and live a life.”

Sinclair and Blichfeld are credited with co-writing and co-directing the vast majority of the series’ run; this season, they trade off directorial duties on every episode. While they have brought in new collaborators for the past couple of seasons, they still primarily steer the ship together. On top of his co-creator responsibilities, Sinclair serves as the face of the show in the role of The Guy, a multi-hyphenate endeavor with clear parallels to Glass’ positions as creator, producer, and host of TAL.

Recalling his early conversations with Glass about “Cycles,” Sinclair explains, “The reason why I went to [Ira] with a workaholic story is because that man is very involved in that show and I think maybe something he’s working on is figuring out how to make it a little more automated and set up so that he doesn’t have to have such a strong presence in it, that it can kind of go on its own hopefully one day.” 

Sinclair does look to This American Life as an example of sustainability that High Maintenance could replicate. They both were on the cutting edge of podcasting and web series, respectively, and each has had an influence on their particular media. Like Glass, Sinclair insists that High Maintenance must constantly evolve if it’s to carry on, even if that means taking a completely different shape in the coming years.

“It has to keep reinventing itself,” Sinclair insists. “It has to be the same and a little bit different. We want to progress, but we also don’t want to be tied to this as our only mode of expression. We also have to let go and let things pass, and know that it will reincarnate later, to not grasp onto this show too tightly, to kind of let it go through us. We have to let things die and compost and give life to something else.”