We all know Sara Bareilles writes absolute bangers—songs with driving beats and almost sermonic messages. Her anthems make us want to write a letter to an ex and burn it by the flame of a scented candle. After “Love Song”—reportedly an angry response to a record label looking for more bankable lyrics—became a staple, we thought, Okay—we get it: Sara Bareilles is a pop star with a twist of integrity. She rocks a side part. She makes us wish we had taken piano lessons.
But we’ve underestimated Sara Bareilles every step of the way. First, she became a major pop star without selling out. Next, she’s succeeded where many, many successful musicians have failed—we’re talking Bono, Sting, and Sheryl Crow—in that she wrote original music and lyrics for what became a hit Broadway musical, Waitress. The songs of Waitress have touched people so deeply, they’ve inspired countless covers and a full-on TikTok trend.
Okay, we thought. We get it: She’s a singer-songwriter, and she’s also a theater nerd who got the last laugh. Then in May, Bareilles starred in Girls5Eva, a TV musical comedy on NBC’s Peacock from Tina Fey and Meredith Scardino. Bareilles is so effortlessly funny, it’s almost crazy-making—how is this the same woman we’ve been bopping to on the radio for so many years? Why hasn’t she hosted SNL?
Bareilles isn’t offended that people are surprised. “I’m surprised too,” she tells Glamour, laughing. Her funny acting self is the part of her that only her friends had known before Girls5Eva. “I think humor is one of the secrets to making it through this life.”
Now she’s back at the piano—she just released her new live album Amidst the Chaos: Live at the Hollywood Bowl, recorded in 2019 and delayed during the pandemic. Recently she performed her first live show in New York City since 2020—a fundraiser for a nonprofit that brings free meals to homebound people.“It was just a tremendous gift to return to the stage and to return to human beings in seats,” she says, her voice catching in a very real, very Sara Bareilles way. “It was just—a miracle.”
In some ways Bareilles even underestimated herself—she never thought she would write a book, produce a show, or act on TV. “Life has showed up bigger and better than I ever could have imagined,” she says. Celebrating her new album and the return of live music, Glamour sat down with Bareilles to break down the real stories behind some of her greatest hits for an installment of our new series, 5 Songs, 5 Stories.
“Gravity”
“Gravity” is Bareilles’s sleeper hit—she wrote it as a teenager as a kind of letter to her high school boyfriend, long before she was attached to an agent or a studio. When her first album, Careful Confessions, was released in 2004, “Gravity” was the first track. It’s the oldest song Bareilles plays in public and a fan favorite.
I wrote “Gravity” when I was about 18 years old. It’s the first time I processed my intimate personal experience in a song in a way that expanded out to deal with metaphor and these larger themes. “Gravity” is really about having my heart broken by another person and feeling physically unable to keep myself away. It didn’t matter how much I would give myself pep talks, or feel my own resolve in moving forward, or think, He treated me poorly so we’re over. I just felt like I physically didn’t have the strength to not respond to his calls, or not go see him if he asked me to. Those kinds of things felt like a gravitational pull. I think the reason that song remains so special to me is that I got to see for the first time that as brave as I could be in sharing my vulnerability, the more connective it was for my audience. I couldn’t possibly have imagined that the song would have this life. It was never on the radio! To have a song that never ended up on the radio be probably my number one, most-requested song is a very special thing.
“Love Song”
“Love Song” was the debut single on Bareilles’s first studio album with a major music label. The song, released in 2007, rose to number four on the Billboard Hot 100, spending more than 40 weeks in the charts. Bareilles earned two Grammy nominations for it—song of the year and best female pop performance.
To be perfectly honest, over the years the story of Love Song has gotten shortened to a one-liner that’s less factually accurate. The song wasn’t a specific response to my record company. Nobody sat me down and said, “I need this kind of song from you.” There was more of a subtle, nuanced…withholding. I was getting ready to release the first record, and I had a whole boatload of songs, so I was like, “What’s the deal? Let’s get in the studio. Let’s make the record.” There was a withholding of the green light. I was encouraged to keep writing and to meet with cowriters. The cowriter thing was a total disaster, devastating on every level. I felt invisible and unimportant and manipulated and all the things. But I knew—because I’m a smart person—that they didn’t have a song they felt they could go to radio with. So I shifted to the idea of a love song.
I even referenced Maroon 5 in the lyrics—those were people I knew very closely and was touring with. I made it so, so deeply specific to my experience, I thought that they would be angry with me. I thought my A&R guy was going to get mad. He actually remains a really good friend of mine! He had no idea until I was like, “It’s kind of…about you.” And he was like, “That’s amazing!” It was a response to feeling invisible and knowing that I wasn’t going to be manipulated. I was so stubborn, especially at that age. I was so protective of myself—I wasn’t going to do what they asked me to do. I wasn’t going to wear the sparkly dress, I wasn’t going to wear the high heels. In some ways, I probably wasn’t having as much fun as I could have had. I was so concerned with losing myself, somehow, in the process.
This song was my little stubborn “fuck you.” The music industry, and the entertainment industry at large, can be a really toxic place. For someone like me who’s prone to a lot of depression and anxiety and self-doubt, I know that I have to manage my mental state in a really rigorous way. I think I felt protective of myself, but the song ended up opening all these doors for me and taking me around the world.
“Brave”
“Brave,” released in 2013 in the heat of the marriage equality movement, was the first single on Bareilles’s fourth album, The Blessed Unrest. It charted in the Top 40 of several different countries, including the U.S., Australia, South Korea, Japan, New Zealand, Canada, and the U.K., and earned Bareilles a Grammy nomination for best solo performance.
I couldn’t have written this song without Jack Antonoff. It’s one of the first times I had a cowriting experience that was really positive. He has an ability to make things feel worthy of being an anthem. It’s like he can fill a stadium with his message, and it somehow doesn’t feel overwritten or overproduced—he’s a megaphone. I think one of the reasons it was such a successful pairing is that he was like, “I have nothing to say, lyrically. You don’t need anybody to tell you how to write lyrics.” I felt like I was given all this space.
The Marriage Equality Act was really present at the time. He was launching the Ally Coalition with his sister, Rachel. I basically wrote a letter to one of my good friends who was struggling with coming out. We were adults at this point, and I felt like—this person is so shiny and has so much beauty and so much joy! To feel like there was any part of them that felt like it had to be small or diminished in some way broke my heart. I wanted to write them a message that wasn’t even about outcomes. I think that’s why I continue to love this song, because it has nothing to do with winning. It speaks to courage. All we can do in this life is try to show up with courage, because so much of what happens will be out of our control. But if we can summon the strength to be brave, we’ve done what we can do.
That song in particular has been such an incredible teacher to me. I wrote it in a very high key and then had to learn how to sing it live—so it was really humbling to have this big message I wanted to share and have to really work to do it. I also thought, Wow this song is going to hit the top of the charts! I had all these ideas about what this song was going to do, and none of it happened! What happened with that song was that there was a little bit of a kerfuffle in the media about Katy Perry’s “Roar” and whether it stole my idea. Katy’s a friend of mine, and I had zero beef with her about any of it, so I was like, “This is hilarious that they’re trying to make us mad at each other.”
And then a children’s hospital in Minnesota used the song to highlight patients in their cancer ward, and it ended up in the news. The song had this new life and started being about claiming your own narrative through illness or divorce or whatever. I’m of the philosophy that music doesn’t really belong to us anyway—if I do my job right, I show up and something comes through me rather than belongs to me. I get to be on the ride of that song, and that’s a real pleasure and a privilege.
“She Used to Be Mine”
“She Used to Be Mine” is a ballad sung at the emotional climax of Bareilles’s stage musical, Waitress, the Broadway adaptation of the 2007 movie. The musical was nominated for best musical at the Tony Awards, and Bareilles was nominated for best original score. “She Used to Be Mine” has enjoyed crossover appeal—it is frequently covered by stage and screen divas, and Bareilles released it as a single.
I was a musical theater lover growing up. Those were the first records I listened to. I did a lot of singing into the mirror as a kid, just kind of play-acting from my favorite cast albums. When I imagined myself as a performer as a kid, I was always on a theater stage. Then my life took a left turn and I went toward the pop music industry. I didn’t realize what a beautiful homecoming it would feel to return to the theater. It actually didn’t feel like new territory; it felt like very familiar territory and in some ways the perfect marriage for my songwriting style. I’m really interested in storytelling and character perspective and getting from point A to point B inside a song. It was a relief to get to write in that style.
I found a lot of synergy between Jenna—the lead character in Waitress, who finds herself inside a life she didn’t exactly design—and myself. I had just moved to New York City, I had just blown up my relationship, my band, my professional relationships, and I had left my manager. I was like, “Fucking what am I doing? I’m having a midlife crisis!” I started working on Waitress and poured a lot of that emotional architecture into these songs. I’m so grateful it was a successful venture, mostly because I really love that source material. Adrienne Shelly’s movie is so beautiful and poignant, and that show’s had a life beyond anything I could ever have imagined.
“Saint Honesty”
“Saint Honesty” is a Grammy-winning single off her sixth studio album, Amidst the Chaos, released in 2019. Bareilles performed the song as the musical guest on Saturday Night Live in April 2019 and again for her live album, Amidst the Chaos: Live From the Hollywood Bowl.
This is the song I won a Grammy for; I got best American roots performance last year for it. It’s a song I wrote with Lori McKenna, who is a dear friend and a beautiful songwriter. We recorded that song in one take in a studio—I was working with T Bone Burnett, who is someone I had always wanted to make a record with. He encouraged me to just sing and play with the band. It was something I was always really nervous about doing. I felt like, What if I make a mistake? But he was really encouraging, so I did it. And we got the song.
There’s something really special about that—it felt like a little moment of growth for me as a person. I really believe in this message—we are healed by what is true. It’s about courage to step in to those places of truth and light, and to share what can be painful. I do feel like the truth can set us free. I am as honest in my personal life as I am in my music, probably to the detriment of my relationships. My boyfriend and I laugh about it, because he’s like, “You know…sometimes you could just lie a little bit!” Sometimes I get into a muddy zone when my honesty overtakes my tact. I’m working on it. I try to frame it in kindness. I’m not a saint—I fuck up all the time, and I do plenty of hurting people’s feelings, but I do really have good intentions. I really believe that for me to preach about living an authentic life, I need to show up that way.
Jenny Singer is a staff writer for Glamour. You can follow her on Twitter.
