Interview: A New Slice of Pie for Sara Bareilles as Waitress Heads to the Big Screen

The composer/star looks back on an unexpected journey that changed her life.

When Sara Bareilles embarked on the creation of Waitress with book writer Jessie Nelson, she never expected her journey to take the route that it did. From songwriter (Bareilles earned a Tony nomination for her score) to eventual star, Waitress changed Bareilles’s life: not only did she get to explore facets of a career she never thought to imagine, but the show introduced her to her now-fiancee, Joe Tippett.

Waitress, which originated as a non-musical film by the late Adrienne Shelly, is headed back to the big screen this week for five nights, but it’s the musical version. Filmed live on stage during its post-Covid return engagement, the cast is made up of a supergroup of Waitress alums, led by Bareilles herself as pie maker Jenna. Below, she tells us about this very unexpected but happy journey.

Still 1 from WAITRESS THE MUSICAL Courtesy Bleecker Street
Charity Angél Dawson, Sara Bareilles, and Caitlin Houlahan in Waitress: the Musical
(© Bleecker Street)

This conversation has been condensed and edited for clarity.

How has your relationship with Waitress changed over the years as you went from cocreator to star?
I remember it took about two years of working on the show before I even really liked it that much. It wasn’t that I didn’t like it; I was just like “I don’t know what we’re doing. I’m not quite sure what this is.” The process is so overwhelming and so iterative, and that’s very different than the way it had worked for me, musically speaking. So I was just like “Oh my God, it’s so tedious to make this thing.” I don’t know what happened, but a couple of years in, I turned a corner and drank the Kool Aid, and then I literally reorganized by life to make Waitress the centerpiece of everything.

Which not every celebrity composer does or is even willing to do.
When I look back on it, it didn’t feel like a conscious choice. It just felt like what is required because this is how much I love what we’re making. I moved mountains to make sure that I was available for all the rehearsals. I stopped doing anything but this show for years. I couldn’t have imagined not being in the casting sessions. That would have been insane. I would never, ever have chosen not to be there.

And then, you know, the show keeps taking these big left turns, and certainly within my life of going from composer to just watching it and loving it and being a fan and being moved by the material, there was this alchemy between Jessie Nelson and I and, of course, Adrienne Shelly, who is the heartbeat of this entire project, where I would just be carried away by my own songs or by Jessie’s beautiful script. There’s something happening here that’s just resonant on an emotional level. It was just so heart-forward and feminine and it really spoke to me. Like I said, it’s been the reorganizing principle of my life. I’m even marrying a man I met in this show [costar Joe Tippett, who plays Jenna’s abusive husband Earl].

Why was this particular company the right cast to film it with?
We had done the show enough times together. It was kind of like an all-star company. The show really pops in lots of different iterations, but this certainly was a dream come true cast for me. I had done most of my work on stage with Charity Angél Dawson and Caitlin Houlahan, and they are deeply brilliant and the story feels so tender and truthful on both of them.

I’m glad Chris Fitzgerald’s magnificent weirdness was captured for all time.
Me too. He’s a genius. He’s a legitimate clown. He’s one of the greats and endlessly inventive. That role is so interesting. The truth has to be intact, and that goes for every character in the show. Tonally, what we’re doing is a little delicate and tricky because it’s lightness and darkness butted up next to each other. The truth has to be the mainstay. People would audition and you can see them think they’re playing one thing, and you can watch this character change into these wild versions of itself. But it highlights Chris’s genius because his superpower is truth. He can get as weird as he wants because he is 1000 percent believing every beat.

Does this experience, and more recently Into the Woods, mean we’re going to see more theater work from you? Is this part of your life forever now?
Yeah. I mean, I don’t think of it as an either or.

Is it always “or?” Is it never “and?”
Right. I won’t stop making records or stop touring, but theater is one of those things where, once I started doing it, I realized it was feeding me so much. I’m working on something right now and it’s just so joyful to create for theater. I can’t even compare it to anything else. It’s even different than writing music for myself. There’s something about the collaborative essence of theater, especially when you’re telling a story that you love, that really speaks to me, especially as I get older. I’m in my mid-40s now and I want to go where it’s warm, you know what I mean?

As a theater kid who probably grew up on the old PBS tapings of shows, what does it mean to you that Waitress is now going to live alongside all of those for posterity?
It’s a thrill. I know what it feels like to love something and not have access. I love that the theater industry in general is embracing this form of sharing what happens on stage. I don’t think it will ever be the perfect substitute for going to a show. What happens inside those four walls is even more magical and it’s always worth going to see the show live. But I do think this is a beautiful surrogate for the people who really can’t — for a lot of people, it’s not a reality to come to New York and spend the money on these tickets — so this is a wonderful proxy.