Five minutes into the new season of High Maintenance, we get the most ambitious crossover event in history for the NPR-tote-bag set: an appearance by the This American Life staff. Co-creator and star Ben Sinclair focused the first episode’s main plot on a fictional producer for the show named Yara (Natalie Woolams-Torres), bringing in host Ira Glass and the rest of the actual team to film pitch meetings around her.

Not only had Glass been a longtime fan of High Maintenance—a series consisting of sweetly droll, intimate vignettes all interconnected by an affable weed-delivery man known only as “the Guy”—but there’s an obvious kinship between the two projects. “It's out to entertain, but it's also out to take you into these little worlds in this way that I really love,” Glass told GQ. “And I think that's why I got so excited about the show, because I feel like that's exactly our mission. We want to take you into a world, we want to tell you a little story, we want you to get close to these characters, but we also really, really want to entertain you.”

Glass also talked about how the episode came together, his one big drug story, and why you absolutely shouldn’t say Santa isn’t real on the radio. (And yes, he sounds exactly like Ira Glass on the phone.)

GQ: So how did the appearance come about? Both shows are obviously so spiritually aligned, but what’s the backstory as to how you got together?

Glass: I had been a fan of the show and of the Vimeo series. And then somebody on staff met Ben Sinclair, and he came to our staff Christmas party in 2018. Months later, we arranged for his writing staff and Katja [Blichfeld] to come and do a meeting with our staff. Sometimes we'll have journalists who are doing work that we admire come and talk to us about, like, "How did you think about this story? How did you get to the structure? How do you get the sources to open up?" We'd never done it with people who do a fictional television show. But it was really interesting hearing about the little exercises they give themselves [when they] go into different parts of New York and try to find stories.

Mhmm.

And then at some point Ben started pitching different ideas for what the story could be. The early stuff that he was pitching was mostly stuff that related to his own frustrations of running a show, and ideas that he has that nobody on his staff want to do. And he was like, "Let me give that to you. Let me make that story about you."

But it took a while for him to come to the idea of “Let’s have a story where there's a producer of the show, who does this thing of doing an interview that is intended as kind of an innocent exploration of something and then just becomes very serious.” And he was basing this on Elna Baker, a producer on our show. Elna had done a story on our show called “Tell Me I'm Fat.” The part that Ben was interested in was this thing had happened when she was talking to her then husband on tape. And in the middle of the interview, he says this thing to her that she finds so disturbing that it actually becomes a real issue between them. And she tries to talk to them about how devastating that is to hear, and it leads to a whole very difficult discussion on tape. Ben thought, like, "That's good drama. That's a good story."