Indexbit-Sara Bareilles thought 'Into the Woods' would last 2 weeks — she ended up on Broadway

When singer-songwriter Sara Bareilles joined a small revival of Into the Woods in 2022,Indexbit she expected it to be a quick commitment. Part of the New York City Center's Encores! series, the show was a stripped-down version of the musical with a limited run.

But the production, which reimagines familiar fairy tales, was so well-received, it went on to Broadway — and Bareilles had to decide whether to continue in her role of the Baker's Wife, or to move forward with the other projects she had planned for the year. She opted for Broadway.

"What I love about theater is that every reinvention is a chance to find something new, and the new cast brought new kinds of interpretations and heart to the experience," she says. "And I'm so glad that I said yes."

In February, the Broadway cast recording of Into the Woods won the Grammy for best musical theater album. More recently, the show received six Tony nominations, including a nod to Bareilles for best lead actress in a musical.

Beyond the accolades, Bareilles says the Broadway revival holds special significance as the first Stephen Sondheim production that's been mounted since the legendary composer and lyricist's death in 2021.

"There was ... this other layer of reverence, I think, that went into the making of the show, because it was very tender to make something without [Sondheim]," she says.

Bareilles is no stranger to Broadway; about 10 years ago, she signed on to write the songs for Waitress, a musical adaptation of the 2007 independent film. Though she was already an experienced songwriter — her 2007 hit "Love Song" was nominated for a Grammy — Bareilles remembers being initially daunted by the task.

"I was a little bit miserable for the first two years," Bareilles says. "And then I fell madly, deeply devotionally in love. [Waitress] is the the love of my artistic life. It's changed everything about me, everything about my life, my relationships, my career."

Bareilles made her Broadway debut in 2017, playing the lead in Waitress. In 2021, she began starring in Girls5Eva, a TV comedy about a one-hit-wonder girl pop group from the 1990s trying for a second chance.

Interview Highlights

On what makes Sondheim difficult to sing

[Into the Woods] was my first Sondheim show, and the show itself is very fast paced. The scenes are short. There's a lot of repetition. It's a maze. It's this very intricate braiding together of fairy tale characters. ...

The grand intervals are insane. It's like pointillism in vocal performance. It's all over the place and it's short phrases and really dense lyrics that have a lot of information. You really have to be on your words. For me, it was trying to find a balance between sort of like the pop stylings of how I normally sing and something that leans a little more legit and a little more musical theater just to make sure that clarity was really at the forefront. It was really important to me to make sure that every word of this really incredible score was super crystal clear.

On the character of the Baker's Wife

I gave her a name. That was the first thing I did. I named her Rebecca. I like characters that feel sort of torn between two things because I think I always relate to that sense of, yes, my life is extraordinary, and I wonder about other things, too. I think that it's just a very human condition to be questioning who you are and where you are and why you're there.

I love her sort of fascination with the prince. I think it's kind of delicious and silly and very childlike. She's got a thing for royalty. She's like the person who buys the ceramic plates of the royal family. She just loves him ... but she doesn't really know why. It's like an unexamined part of her psyche. And then she gets this chance encounter and it's that beautiful thing where she explores and she makes a mistake. She screws up. It's a messy situation and she still has to reconcile with that. So I love that she's not tied up in a little bow at all.

On the difference between singing a song as a character versus singing as herself

I think the biggest change is something I learned from doing Waitress — I wrote all of the music for that show. So going into the show, I think my approach initially had been as the songwriter and I had to learn [that] a character doesn't know what the end of the song is yet. A character's in it, moment, to moment, to moment. So every thought is a new idea and coming from somewhere and attached to the thought that had come before.

It's what I love about acting actually, is it's a real meditation and staying present where you are just in this moment right now. ... It's just that you're having to watch someone in real time go from A to B to C. And as a songwriter, the agreement with the audience is that we all know I wrote it. We all know I know what's coming next. It's been prepared. But as an actor, you have to sort of disappear into the journey and let your character's discoveries be center stage.

On her initial resistance to taking medication for her anxiety

I was scared that I would get sort of pulled farther away from myself. My melancholy is a big part of my motivation as a writer, seeing sadness and wanting to translate and articulate it, or observing a tenderness in some situation or in a person. I was afraid that [by] being on medication, that something would get subdued, or something would get suppressed, or my feelings would just feel muted or like there was a blanket over them.

I had all these ideas about what it would feel like to be on medication without having tried it. ... I got lucky. It was my first try that I actually started to feel better. And that is not the path for a lot of people. And I know it can be a really frustrating and scary time, but ... it was mythology to believe that that sadness was somehow my source material. It's a part of it, but when the sadness starts to become the North Star or, like, the organizing principle, that's out of balance. That's not telling the truth. That's actually telling a lie. ...

I never wanted to be on medication. ... And then I really got to, like, the bottom of the well and couldn't find out after the pandemic. I think the magnitude of the grief and the magnitude of the loss and fear and political discord and disappointment and how so many things were handled just on a large scale and then just interpersonally, I couldn't pull up. ... [Medication] has been a game changer for me. In terms of quality of life and capacity to hold uncomfortable feelings, it's a much better way to walk through the world.

On satirizing the music industry in Girls5eva and playing a popstar

I didn't have the confidence then, and I almost kind of don't have the confidence now. Like, we had a moment on set ... we were taking still photos that were going to go up on a poster of somebody's bedroom. And I got put in this skimpy black stage wear, like a flashy little black dress, [and] I was in tears. I've had incredible body dysmorphia my whole life, partially from being teased as a kid and being told I was fat and being told I was ugly. And all that stuff still very much lives in my body and in my mind.

And in a way, this show is giving me an opportunity to maybe heal some of that, but I still get overwhelmed with that. ... I get to relive that and kind of try to heal a little bit of that in myself, where we get to wear ridiculous things. And yes, I might cry on set sometimes. But honestly, if you knew the four of us, we are always crying and it's the most delicious, amazing cast of women. We're very, very close friends at this point.

Seth Kelley and Susan Nyakundi produced and edited this interview for broadcast. Bridget Bentz, Molly Seavy-Nesper and Beth Novey adapted it for the web.