36 Questions and the Future Of Musicals


36 Questions, the new musical podcast written and composed by Chamber Band‘s Christopher Littler and Ellen Winter, begins with a betrayal. Jason discovers that his wife Judith has been lying about her identity throughout their relationship. Voiced by Jonthan Groff, Jason retreats to his family country house, only to be followed by Judith (Jessie Shelton), who hopes to “make things right.” Judith’s plan is a simple one: together, they will go through a list of 36 questions designed to make two people fall in love.

Produced by Zack Akers and Skip Bronkie, the duo behind 2015’s podcast thriller Limetown, and told across three acts, 36 Questions is a love story re-examined. With just two characters, it is much more intimate than the term musical might suggest.

EMMA BROWN: How did you first meet Zack Akers and Skip Bronkie? I know you worked on Limetown, Chris, was it through that?

CHRISTOPHER LITTLER: I met Skip and Zack freshman year of college, actually. I lived with Zack; we were freshman year roomies and just became friends. We never really worked together creatively until 10 years after college when Limetown hit. They released Episode One of Limetown and it became huge. They came to me: “Are you able to write any episodes, because we cannot keep up?” I was like, “I’d love to write a spooky, scary Limetown episode.”

[Skip and Zack] are disruptors. They want to do something new; they want to play around with format. That’s where 36 Questions came from. They were like, “Here’s a crazy thing that we know nothing about. Let’s make it.”

ELLEN WINTER: They knew they wanted it to be a musical podcast and they had the one sentence defining it: it’s about a couple whose marriage is on the rocks, and the only potential way to salvage it is these questions. That was what we were given, and we were like, “Great! That sounds really difficult to do, and we’re so on board for it.” [laughs] It was just enough. Having that sentence, having that place to go from, was really juicy to us. The fact that it was a form that hadn’t really been explored a whole lot before was also really exciting to us as writers and creators. They spoke with Chris first about it, and then Chris actually brought me on.

BROWN: I know you’re both in a band together, but did you have much experience as writers?

LITTLER: Yeah, I think that’s where a lot of our overlap is. We’re both dramatists. I went to school specifically for TV writing, so I’m kind of a rigid structuralist. Ellen has written lots of plays and musicals.

WINTER: I did playwriting in college and also studied composition and performance. All of our Chamber Band albums, they’re songs written in established universes, so finding ways to integrate story into song is something that we’re familiar with. It was fun to push that to another level of narrative in this form.

BROWN: How do the two of you work together? Are you generally in the same room, or is more via email? Does one write the melody and the other the lyrics?

WINTER: We’re basically workers of necessity. We work in the same room when we can.

LITTLER: For this show, it was a lot of Ellen at the piano, and me sitting right by the piano. She’d go, [hums] “Hmm hmm hmm” and I’d go,”There it is!” I’d get up and pace around; Ellen would come up with lyrics on the fly, kind of Wayne Brady-style. We were recording the whole thing, and we’d go back over it: “This is garbage; this is gold.”

WINTER: [laughs] “These 10 seconds makes a lot of sense.”

LITTLER: That was the beginning process, having all of these song nuggets and moments that made sense. That’s how we started to organize things. We knew that, really, the hardest part of a musical is having a reason for someone to sing, and having an emotion that’s strong enough that someone has to sing it. At that point we were off to the races. We would have a problem, meet with our producers, chug ahead a little more on the story, go back to the drawing board, and do the same thing over and over again for about a year and a half.

WINTER: Chris would take a pass at a scene and then I would take a pass at a scene; I would take a pass at the lyrics and then Chris would take a pass at the lyrics. It was a lot of back and forth. It was a really invigorating and collaborative process at every turn.

BROWN: The show is divided into three acts, and during the first act, you only get through about two of the questions referenced in the title. Did you originally plan to get through a set number of questions during each act?

LITTLER: The idea was there for a while.

WINTER: The questions themselves are divided into three sets of 12. But then we realized that that was unnecessary information—to force 12 questions into each episode didn’t feel right. We started listening to the narrative instead of the form.

LITTLER: We’re big believers in content dictating form. It’s always: What does the character need? What’s actually happening right now? What do we actually care about? We came to the three acts pretty late in the game.

WINTER: We thought it was going to be two-parter for a while. And then we were like, “We cannot possibly get this whole story in.”

LITTLER: It was really hard to write. I’ll say that. Musicals are hard for the reasons we said before, and in a podcast, you have to be overly explicit, or someone has to be explicit, whether it’s the narrator saying, “Chris picked up the recorder” or, “I am picking up the recorder.” We had to solve that problem. Then it’s a show about these questions and, as a listener, you’re like, “Are there going to be 36 questions? Are they going to get through them all? Do they have an order?”

WINTER: There was a lot of maintenance of clocking all of the things we needed to be aware of in every waking moment of the show to justify every word, every line—to make sure that we’re not losing or mistreating the listener, make sure that they are aware of what’s happening and that they are on the emotional journey with the characters.

LITTLER: The answers can be boring unless the stakes are incredibly high and everything is loaded. Every answer has one of the characters sifting through it: “Are you telling the truth or not?” That felt really important.

WINTER: We went through a lot of different versions of the narrative, the script, and the story. Early, early drafts had a chorus; early drafts had a narrator. I was the narrator at one point as the music director. But then we realized that we weren’t really leaning into the capabilities and the advantages of it being a podcast. We were like, “Okay, what are things that we can do in this form of storytelling that you can’t do on stage and vice-versa?” One of them, being in a band, was layering vocals. We realized we didn’t need a chorus if we had this studio time where we could really create these layered voice parts—not out of ensemble members that we’re trying to justify existing, but the two people who are leading us in the story. By the same effect we were like, “How can we get rid of the narrator or give that agency to Judith?” I think that was a big turning point, too, in our discovery of the narrative—giving that agency to Judith and letting her take the lead and drive the story forward.

LITTLER: The action is her recording.

BROWN: At the beginning of Act One, Judith tells Jason that she records certain moments for when she’ll miss them. That seems like a terrible idea.

LITTLER: Some serious hubris going on. Stay tuned.

BROWN: Did you feel like you were both equally each character? When you were writing, did one come more naturally than the other?


WINTER: I’m more a Jase.

LITTLER: And I’m more of a Judith.

WINTER: There were a lot of moments in writing it where I would take a pass at a Judith song and Chris would be like, “Ellen, you wrote a Jase song.”  

BROWN: Was that divide intentional or something that happened naturally as the characters evolved?

LITTLER: We knew that we needed them to be diametrically opposed; they needed to be an unlikely couple so they would have a lot of reasons to fight.

WINTER: I feel like Judith became more fully realized in the later drafts. We knew we didn’t want to write a gender normative piece about a heterosexual couple; we didn’t want to fall into the stereotypes of what a husband might necessarily be or what a wife might necessarily be. We knew that Jase was an emotionally intelligent human, and we wanted that emotional intelligence to dictate his story.

LITTLER: Are you saying that men don’t have emotional intelligence?

WINTER: No! I’m saying that I do think men have emotional intelligence. There are a lot of examples in the film and movie world that don’t necessarily depict men in that way, and I think that’s detrimental to a lot of men’s emotional journeys. We knew we wanted to push back against that and the typical romance story.

LITTLER: The typical romance story is man lies to woman—

WINTER: Woman is wronged.

BROWN: Did you always plan to have a heterosexual couple?

LITTLER: That’s baked into it, so we did know that. Also, just from a practical perspective, a female voice and a male voice in a podcast allow you to differentiate. It’s really tough. You think you can get away with stuff in this format, but there’s very little you can get away with in terms of clarity. If we were even to have one more character, it would make it exponentially harder for people to track what’s going on.

BROWN: Are we not going to meet Jason’s mothers? I would like to meet the mothers.

LITTLER: Maybe there will be bonus content in the future, depending how successful it is. [laughs]

WINTER: I love the moms. I have such vivid imagery of Jase and his moms hanging out.

LITTLER: I see it in my mind too.

BROWN: I like the sound of their house and their colonial quilts.

LITTLER: It seems like they have a nice little life. They raised a good boy.

WINTER: He’s a nice man. She’s cool too, though. As we wrote more and learned more about the characters, we found ways to deeply relate to both of them. I think that’s the joy of this piece, if people enjoy it. You might be team Jase at the beginning and then, by the end of the series, more like, “Oh, I actually understand Judith” or, “I see myself in her in ways that I didn’t want to.” [laughs]  

BROWN: During the songwriting process, was it about how each song made sense as part of the larger narrative, or was it more finding one or two songs that people would want to belt out in the shower and listen to over and over again?

LITTLER: It had to do with both in a way. There are songs that have to do a lot of heavy lifting from a narrative perspective to get you from point A to point B, and there are songs that are sinking into a single moment.

WINTER: To be totally transparent, I’m not usually thinking about how people are going to hear and embody these songs; it’s what feels right in the turns of the songs. It isn’t until after the songs are written that we’re like, “Oh, this could be something that people really enjoy belting in the shower.” A big part of of the initial writing process was churning out as many songs as we could, and chord progressions and melodies and ideas. When we were coming up with the story, we had this list of generated material where we were like, “That song is this emotional moment!” We were of able to put them together and solve the rest of the song based on that narrative.

LITTLER: We’re problem solving. Most of these songs were written in an hour and a half. If you know the intention and you know the melody, it’s there. It’s not the finished version of it, but it just comes out of you. Any time we were taking three days on a song, there was that red light going off telling us that it wasn’t right: “There’s no song here guys, so accept it, bury it, move on, and find another wave.” Our bassist in our band, Anthony Cerretani, he’s one of those guys who’s like, “I hate musical theater.” I remember going through [musical] songs with him: “Here’s a Sondheim song,” and he was like, “I just don’t like all of those voices. If there are 20 people singing, I just don’t like it.” So we played him the first song from Natasha, Pierre, and the Great Comet of 1812, and he was like, “Alright, I can get into this.” I think it was that all of the characters singing had justification in singing together, because they were introducing themselves. He understood the context of the chorus.

BROWN: Acting for the stage and acting for the camera are very different in terms of the size of the performance. What is acting for a podcast like? Were there moments where you had to ask Jonathan and Jessie to bring it down, or take their performance up?

WINTER: It was a lot of that. I was really grateful for the time we had spent in studios recording albums because we had an idea of the sounds that we were going for and techniques. I used to do musical theater and stage performing, and I know that I had to clock, when I first started recording in the studio, that belting is not actually going to serve the story or the listener. There were moments where, had the song been performed on stage, that would have been the time to belt it and go balls to the wall and sing for the people in the back. But the people are actually right next to you, so how do you make this a true, emotional moment while not compromising the intimacy of the sound?

LITTLER: From a drama perspective, Jonathan taught me a lot about what it means to do comic scene work on an audio level, because he’s been doing it at the highest level. I wish I had video of it, because everything is so big when he does it so that you can feel it in his voice. We call it snowshoeing, because when they’re walking, they have to walk in such an absurd way.

WINTER: I have a video, actually, on my phone. It’s the scene where they’re out by the car and it starts storming and they have to run back to the house. It’s a video of Jessie and Jonathan, and they’re both running in place and talking to each other. They look absolutely bonkers, but it makes all the difference.