18 Questions About "36 Questions"

Stuart Spencer

This space is normally devoted to critical looks at the dramaturgy of plays and musicals currently playing in New York, but after only two columns I’m already breaking the pattern. It’s for two good reasons. First, I recently listened to the world’s first podcast musical, 36 Questions, written and composed by Ellen Winter and Chris Littler. 36 Questions is not only an exciting idea, it’s also a cunningly written piece, as finely crafted as it is cutting edge. Second, I have the great good fortune to know Ellen Winter, who was a student of mine at Sarah Lawrence College where she studied theatre history and playwriting with me. I couldn’t resist the opportunity to speak to her and her collaborator, Chris Littler, about the show and how they put it together … bit by bit, piece by piece …

SS: Congratulations on inventing a new art form. I don’t imagine I’ll do many interviews that begin with that statement. But before we get to that, let’s start with the basics. Who does what in your collaboration?

CL: We both have a specialty, but everything passes through both of us several times. The genesis of the songs is usually Ellen, and the genesis of the plot ideas is usually me, and then we each take a pass at it, and see how it weaves together.

EW: It’s a shared effort all around. We’re really fortunate to have that in our partnership. Because there were times when I said, “I can’t look at this scene anymore, can you take it? I can’t figure out how to get them to this moment. Or I would write a million drafts of a lyric, or everything but the chorus, and I would give it to Chris and say, “How do we get to the chorus?”

SS: I read that your producers came to you with the essential idea. What were the parameters they handed you?

CL: We were given the log line to the show, which is that a marriage is on the rocks, and the husband and wife use the ’36 questions’ to try to save their marriage. That and the fact that the format would be a podcast musical. From there we had figure out how the story would be told — would it have a narrator, for instance, which it did for a long time.

SS: It was a brave choice to go without one. It certainly adds to the degree of difficulty.

EW: For almost a year, as we were writing it, there was a narrator, but the more we discovered about the plot and who these people were, the less we were able to justify having one. And the idea of having Judith [one of the two main characters] leading us through the story and having that agency — although it did present challenges — proved to be easier than writing a narrator. Because this is a character study and that was what so exciting to us once we cracked the thing.

SS: Were you limited to two characters?

CL: We could have had a standard cast, and there was an early version where we did. But we kept asking, do we really need this? What’s the neatest version of this show?

SS: Writing a full length play, much less a musical, with just two characters is no small feat.

CL: I think we didn’t realize we climbed that hill until after we were over it.

SS: How long did it take to write the show?

CL: A year and a half.

SS: What were the hardest choices you faced in writing it?

EW: We knew we had a set of themes that were exciting to us as writers: listening, identity, and truth. And although these characters are heterosexual, we didn’t want to be heteronormative in how they were presented. We were trying to play against the husband-and-wife stereotypes, and especially against the ‘romantic comedy’ stereotypes. If it started to go too much in that direction, we knew to pull back. And there was a lot in how we were to present the narrative that formed the characters. For instance, once we knew that Judith had another identity, the voice memos became integral to her character because it allowed us to deal with questions like, how do you keep track of a life that you’ve created for yourself? And how do you hold yourself accountable for the mistakes you’ve made?

CL: And we were constantly checking to make sure that the themes were reflected in the choices that we made. For instance, the conceit of the first song is that Judith is knocking on Jase’s door and his first line is ‘whoever you are’ — even though she knows very well it’s Jase. We knew that was right was because that’s about identity. She’s playing a game of sorts, saying “you can be someone else right now.” And even though people might not notice that, or might forget about it, it feels neater because of that. And we do that in several places in the shows.

A lot of choices were made because of the podcast format. We were very conscious of the listener. There would be people who are not musical theatre fans, and others who were. So we knew we had to thread that needle and take care of both audiences.

SS: What did you do to take of, for instance, the musical theatre audience?

CL: The first five minutes of the show is a good example. The rules of musical theatre are that you start with a song. That way, no one questions that you are in a world of music. We struggled with that. We didn’t have a song for the beginning. We really needed to walk the listener to the moment of the first song. Well, podcast audiences love mysteries, so we set it up as a mystery, but at the same time we scored the section so that the musical theatre people wouldn’t be thinking, “Is this really a musical?”

EW: We were excited by the rhythm that can come from a non-musical scene, and that was how we went about scoring them — and eventually how we orchestrated them as well. Another factor was that we went upstate on a writing retreat. And our band-mate came with us to make sure we ate and didn’t die of hunger, and he is not into musicals.

CL: He’d never been to a musical in his life …

EW: … until that night when we played him Natasha and Pierre and Company and other things just to get his hot take on it and see how we could appeal to him. And he really disengaged whenever there was a ton of people singing. And that was a great insight for us: why have a bunch of voices that you can’t place, that the ear can’t distinguish, when you can have a chorus of the two people you’ve already been listening to, and know exactly who they are.

CL: We focus grouped it. A single-person focus group.

SS: Come to think of it, Company actually begins with a long dialogue sequence at the birthday party.

EW: Thanks, Sondheim!

SS: How many elements of traditional musical theatre — the I Want song, the conditional love song, and so on — did you consider using? You must have been aware that at least some of your audience would be sitting there thinking, ‘where’s the I Want song?’

CL: It’s not just that the audience is wondering if we’re going to hit this thing. If you don’t have an I Want song, you don’t really have a show.

EW: There’s a reason why some of those tropes are essential. It was always about how to create one fluid motion to get to the end of what we would call a “movement”, which is the scene that then leads into the song. Where are we at the beginning of the scene, and where are we that’s completely different by the end of the song? “Hear Me Out” is definitely Judith’s I Want song, and “One Thing” is kind of a combination of Jase’s I Want song, but also a kind of conditional love song too.

SS: In some ways, “One Thing” is a neat inversion of the I Want song — it’s all about Jase telling her he doesn’t want her, and please go away.

CL: His real I Want doesn’t come until the end of Act 2 and “Reality”.

SS: Any other musical theatre tropes that you deliberately used?

CL: The 11 O’Clock Number. “Attachment” is there because we knew we needed something big at the end, otherwise it just descends too far into sadness.

EW: Because it’s in three acts, each of those tropes have a different roles, depending on where we are in the story. And each episode has to have its own arc, so we sort of hit all of them, or most of them in each episode.

SS: I think it’s been a hundred years since we’ve since we’ve seen a three-act musical, by the way. What made you make that choice?

EW: Originally, when we were pitched this idea, the dream was that it would be episodic, somewhere between 6 and 10 episodes. But about half through our process we stepped back to look at the story and the plot and these characters to figure out what was best serving them. The episodic structure wasn’t really going to give people what they wanted, so we shrunk it to just two acts. But then halfway through Act 2 we realized we couldn’t possibly fit everything into just 2 acts. And also 3 acts made it sort of a limited mini-series, which we liked.

SS: And the producers were okay with that?

CL: I think one they realized how long it was, they were, like, okay that’s a lot of content …

SS: Songs take a long time.

CL: Yeah, and it’s a crazy journey you have to go on. And also the characters have to do the experiment. The 36 Questions have to be addressed in some way …

EW: … and we knew we had to get through all of them …

CL: … and it became difficult to linger in the questions. It doesn’t move forward fast enough. So it had to be longer in order to address that challenge.

SS: Now that you’re finished, is there anything you wished you’d done differently?

CL: I think it’s perfect. [Laughter]

EW: There were a lot of things we learned in the process of doing this that we will apply in the future on our other projects. But there’s definitely not anything about the show that I’m kicking myself for. We worked our butts off, and the best of the work is the work you’re hearing. And besides, it’s not like a live show that you workshop and get feedback on. There’s nothing we could do to change anything at this point anyway. We’re proud of the work we did. If we do another version of this show, in a different format, there will be more challenges there …

SS: What does the future hold for this show?

CL: We have a lot of people now who are reaching out to us, and we have a lot of offers on the table, and we’re going through them. The question is, what does the world need?

SS: So we may see it, in addition to hearing it.

CL: You might.

SS: Aside from this piece, what else is coming up for you two?

CL: We definitely want to continue to expand the musical podcast world, we love the idea of creating new properties in the podcast medium in different genres. If this is a love story, then what about a thriller, or a mystery? And we’re also interested in doing stuff on stage.

EW: Whatever format we’re working in, we want to subvert their expectations about what they’re going to encounter when they experience it.

CL: And have fun with it.

EW: Take the work seriously, but not ourselves.


36 Questions, starring Jonathan Groff and Jessie Shelton, is available on iTunes as a free download. The album is also available on iTunes and at https://36questions.bandcamp.com/.

Photo: From left, Jessie Shelton and Jonathan Groff, who play the “36 Questions” podcast's characters, and the composers Ellen Winter and Chris Littler. (Allison Grasso)


Stuart Spencer is a playwright and novelist. He teaches playwriting, dramaturgy, and theatre history at Sarah Lawrence College, and is the author of The Playwright’s Guidebook: an Insightful Primer on the Art of Dramatic Writing published by Farrar Straus & Giroux. You can follow him on Facebook.