Sara Bareilles on Her Worst Waitress Idea, Her Next Stage Project and Ann Dowd's Role in Her Latest Emmy Nomination

In some circles, Sara Bareilles is still the singer-songwriter perched behind a piano railing against music industry power brokers in “Love Song.” In others, she’s the face of Waitress, the delicately sweetened musical with an addictive score and the misfortune of landing on Broadway the same Tony season as Hamilton. But if the past few years of Bareilles’ career have proven anything, it’s that definition does not suit her. From stepping into the lead role of her own musical, to crafting an original TV show, to effortlessly melding with Tina Fey’s comedy universe as an actress-for-hire in Girls5Eva (Meredith Scardino’s campy series about a resuscitated ‘90s girl group, also starring Paula Pell, Renée Elise Goldsberry and Busy Philipps), there seem to be no stones Bareilles is willing to leave unturned—no matter how anxiety-inducing.

You could say Waitress was her first leap of faith beyond the piano bench (which she, along with playwright Sarah Ruhl, are now following up with a musical adaptation of Meg Wolitzer’s novel The Interestings), and she’s stuck the landing on every one since: She earned a 2018 Emmy nomination for her performance as Mary Magdalene in NBC’s Jesus Christ Superstar Live in Concert; a 2023 Tony nomination for her performance as the Baker’s Wife in the revival of Into the Woods; and now another Emmy nomination for writing “The Medium Time,” the number she and her sisters in nostalgia performed in the season three finale of Girls5Eva (its first season on Netflix after moving from Peacock). Since season one, Bareilles has provided the show’s annual hit of sentiment in a sea of Jeff Richmond comedy numbers. But that was not a foregone conclusion when she joined the cast as an embryonic TV actor playing the equally embryonic songwriter Dawn Solano. Fortunately, Bareilles’ love language is songwriting and her well of emotion for Girls5Eva runs deep.

Ever since you entered the theater world with Waitress, it seems like so many new avenues in your career have opened up. Is that how it’s felt to you?

Yes, one hundred percent. There's no way I could have known that that would've been an outcome of working on a theater project. I had no comprehension of how much the film and TV industry at large pays attention to what's happening in theater. Waitress is how I met Tina [Fey]. It's why I got cast in this show. It's how I ended up making a TV show with J.J. Abrams. It's how I ended up making a record with T Bone Burnett. There's just so many things that happened from working on Waitress that I am so surprised and delighted by.

And now you’re in the trenches working on a new musical. How did The Interestings become your next stage project?

Sarah [Ruhl] was on board already when I got sent the book and I said, “Well, let me read the book and see.” I knew I was a fan of Sarah, but I know how hard it is to make a musical. And then I just devoured the book. I wrote the first song for the show before I'd even finished the book. I just was like, “This is such a musical to me,” and I'd been kind of waiting for that. I've been sent a lot of things over the years and I wanted to be really discerning about what the next project is. The thing that I love the most about this book is that there's no giant event. It's just humanity. Watching it live on people over a period of time.

When you were writing Waitress, the whole process was brand-new to you. Do you prefer being a blank slate or do you feel more prepared this time around?

I just was so deer-in-headlights for so much Waitress. I was panicked trying to meet the next expectation and the next moment and write songs quickly. I mean, I wrote some pretty f*cking terrible songs for Waitress that thankfully did not make it into the show: I wrote a whole song about dancing sperm singing “please have sex with me.” That was a moment I could have maybe sat with for a few more minutes and just said, “this might not be my best idea.” I think I have a little bit more of a relaxed attitude around it [this time]. I don't feel as panicked.

Is the job of writing songs for Girls5Eva also becoming more comfortable now that you’re three seasons and three big finale songs in?

I give so much credit to Tina and Jeff and Meredith on just how they even offered this, because they knew that I was a little bit of a fish out of water. I'm not someone who came up as an actor. This was a big job for me, and it was something I've never done before, and I knew the learning curve would be really steep. So they basically offered it with no pressure: If it sounds fun to a write something, yay amazing! If you don't want to, no problem. Then over the course of that first season, as my nerves started to quell and I got more comfortable and I fell madly in love with my co-stars, it became like, this is the way I know how to show my love—write songs.

On the show, you’re writing songs as Dawn. How would you describe Dawn’s songwriting voice?

It’s writing for a character who has not been doing this her entire life. She's building up her toolkit again. She's gaining confidence. The world that they've created for Girls5Eva is a little bit heightened, very direct. So I think those flavors live in the music naturally. Jeff Richmond is a comedy song genius. There's nobody like him who can do it the way he can do it. So taking that pressure off of like, I'm not going to be Jeff Richmond. But my fastball is trying to bring the heart and the sincerity out in a moment. So I really played into the Sara of that.

Is there any one person on the Girls5Eva team you most look forward to sharing your new songs with?

It's the three of them. We are on a text chain and I’m usually waiting for the crying emoji to come back. We're all big criers and it’s just very sweet. You’re giving something to your friends that they're going to love.

How does it feel when the four of you get to sing your songs together?

It's so fun. Part of the inspiration for [“The Medium Time”] was us singing about the actress Ann Dowd. We had this whole song about how her career is so illustrious and she disappears into her characters. It didn't make it into the show. But we were so f*cking happy singing this song together that I logged that. I remember being like, oh, this song at the end of the show has to be a park and bark. We are standing and singing four-part harmony and just enjoying the fun of making music together.

It's fitting that all three of your finale songs—“4 Stars,” “Bend Not Break” and now “The Medium Time”—circle similar themes of being happy exactly where you are rather than trying to get somewhere bigger and better. 

That theme lives throughout the entirety of these three seasons, culminating in “The Medium Time,” which is this really beautiful acknowledgement of just how lovely it is to be somewhere in the middle to be with people you love and doing something you love. How that might actually be enough. I really love that as a theme that lives outside of even the world of the show. When do we just let ourselves just f*cking enjoy what we've done?

How well have you learned that lesson for yourself?

Still learning, very much in process. Therapy, medication, meditation. There is no arrival. There's no place I'm trying to get to. I'm just trying to be really awake to what is alive in my life, in front of me, and the ways in which I can adjust to just be in a deeper acceptance of what's here. Because there's always going to be pain and discomfort and disappointment and loss and grief. You can count on those things as being a part of your life experience. Which makes a moment like this to celebrate—gosh, I got to make a show that I really love with people I love and wrote a song that gets recognized like this. It's just really special.