’36 Questions’ Musical Podcast Interview Starring Jessie Shelton and Jonathan Groff


Shelton, Winter, and Groff in the recording studio
Photograph by Alison Grasso

I ‘d hazard a guess that nearly every human on this planet knows the phenomenon that is Hamilton. You’ve probably listened to the soundtrack, which debuted at a historic high on the Billboard charts, and you’ve definitely heard of Lin-Manuel Miranda, the musical-theater visionary who has suddenly found himself a household name. But snagging tickets to see it live? Good luck.

That’s where 36 Questions comes in, a new musical podcast from the creators of 2015’s cult-favorite mystery series Limetown, Zack Akers and Skip Bronkie. Starring Jonathan Groff (of Glee and Frozen fame) and breakout talent Jessie Shelton, it’s a first of its kind: a Broadway-caliber production made specifically for the podcast medium. Which means, of course, it’s free.

The show centers on a young couple whose marriage is on the rocks—Judith (played by Shelton) has been lying to her husband Jase (Groff) about her identity, and wants to use “the 36 questions that lead to love” to save the relationship. It’s charming, moving, and fresh—and the music is incredible (think Once for 2017).

“It’s really exciting to get to share something with people that they don’t have to go to,” says co-writer/director/composer Ellen Winter, who—with Chris Littler, the other half of the creative equation—developed the show over the course of a year and a half. Edited by Serial‘s Kate Bilinski, it has all the addictiveness of the podcasts you’re obsessed with plus all the allure of the musicals you love.

Here, the women of the show give you a peek behind the scenes.


Shelton, left, and Winter, right
Photograph by Alison Grasso

On the importance of telling a story in which a woman has the agency

Ellen Winter: I personally and everyone on the team identifies as a feminist. Because the show is about a heterosexual relationship, we really didn’t want to fall into stereotypical gender norms in how we were presenting it. That was a big part of how the narrative shifted and changed as we developed it—giving Judith more and more agency. The more decisions that we left Judith at the forefront of, where she was at the wheel driving the whole thing, the better the story felt and the more sense it made.

On working with Jonathan Groff

Jessie Shelton: I was intimidated but it wasn’t crippling because I felt very supported. To be working opposite somebody like that in a two-person show…but he was so easy to work with. There was this current of comfort, the way we bounced off each other.


Groff and Shelton
Photograph by Alison Grasso

EW: He’s just a being of pure light. Freaking out is definitely a term one could use to describe how I felt when we cast him—Spring Awakening [which Groff starred in on Broadway and for which he got a Tony nomination] is my favorite musical; I did it in college. He’s just such a pro and such a champ—the day before we went into the studio to start recording, I had written a new song and didn’t have sheet music for it, and Jonathan and I were at the piano and I’m staring into his eyes going, “This is this line, repeat after me.” We would just sing the line over and over and over again until we got it, and he was like, “I’m in. You don’t have sheet music? Amazing, let’s learn it together.”

On performing a love story without being in the same room as your co-star

JS: It’s funny because for most of the recording process in the studio, it was literally just us barely being able to see the side of each other’s faces.

Kate Bilinski: He [Groff] was largely in an isolated box so we could get clean takes. Unfortunately for them it does create the sort of situation where they’re essentially in different rooms. They have to pretend to be right there next to each other, which is a feat.