How Sara Bareilles Evolved Beyond Being a Pop Star

“Love Song” made her famous and sent her out on the road. She played bigger and bigger venues for a few years, put out the album “Kaleidoscope Heart,” and then went on tour and played fifty-two shows.“I could really see clearly, you know, down the road that the life of the touring musician gets very cyclical very quickly, really redundant,” she says. “And I was not that interested in that.” Nevertheless, she scored another megahit with her next album, “Blessed Unrest”—one of whose songs, “Brave,” co-written with the songwriting guru Jack Antonoff, was a pop call to empowerment that Bareilles created for a friend who was struggling with coming out to her parents. (This was when I first met Bareilles’s music, on my nine-year-old daughter’s iPod Shuffle.) “Brave” led to bigger deals, bigger gigs, and more money—she sold out the Hollywood Bowl and Radio City Music Hall—but over time Bareilles, despite relishing the connection to her fans as individuals, was more and more sure that she was heading where she did not want to go.

She may also have anticipated the wall she would surely hit. Being the embodiment of youthful rage, the woman who will not be mansplained to, is a term-limited gig. The culture changes; the new young grow angrier or angry at different things. In 2016, a woman wrote on Twitter, “The only thing I hate more than Sara Bareilles’ music are the girls who listen to Sara Bareilles’ music.” Bareilles was in danger of becoming a meme.

In “Girls5eva,” Bareilles’s character faces a similar bind. The band is remembered nostalgically by fans from its heyday. Younger listeners regard it as ancient history. “It makes me think of my mama’s boobies,” a rapper who samples Girls5eva comments. Another object lesson in the problem: in 2021, a judge on “Masked Singer” incorrectly guessed that Bareilles was the celebrity hiding in the pepper costume. It turned out to be Natasha Bedingfield.

But, in real life, Bareilles was too alert and talented to be trapped. As she was working on “Blessed Unrest,” she moved to New York, “looking for something different”—uncertain, she says, what it would be. She visited in September, the city’s most clement month, in 2012, and found New York to her taste. “I, you know, went out, got drunk, went to parties, met people, saw friends in music, played music. There were creative opportunities that cropped up. It just felt like there was a whole artistic world waiting here.” She took an apartment the following January and first lived in the West Village, then NoLita, before she finally settled uptown.

You couldn’t be a musical actor in New York without bumping into Sondheim sooner or later. One audition, shortly after she arrived, was for a version of “Into the Woods” to be performed as part of the Shakespeare in the Park series. She tried out for the role of Cinderella but did not get a call back. She was not particularly familiar with Sondheim, and her musical taste, though broad, ran more to other genres: Ray Charles, Etta James, the Police, Prince, Fiona Apple, Bill Withers, Joni Mitchell, Paul Simon, Dave Matthews Band, and Death Cab for Cutie were among the influences that she cited in a 2015 U.C.L.A. alumni-magazine interview. When I asked her what musicals she currently likes to sing in the shower, she mentioned “Chess”—“I never saw the show,” she said, “but the music’s great. I love love ABBA.”

Of the Sondheim in the Park audition, she acknowledges that she made a mistake. “I was singing the song,” she remembers, “but I didn’t understand the song. I had not really taken the time to know it.” She had little acting experience, and it was her first real audition, too. She remembers the humiliation she felt as, in retrospect, “good for me. It was humbling, in a deep way. It’s, like, oh, that what people do here, especially in the theatre community, is extraordinary. And it’s really hard, and it requires a lot of dedication and intentionality. And I didn’t have either of those things.”

A couple of months later, she had a happier experience. Diane Paulus, who was the director of the American Repertory Theatre, at Harvard, asked if Bareilles wanted to collaborate on a musical version of “Waitress,” a movie that had come out several years before, written and directed by Adrienne Shelly. The story is of a woman who works in a restaurant, has a child with an abusive husband, and has an affair with her gynecologist. She’s a gifted baker who makes pie to relieve her misery. Bareilles, who no one knew could do this sort of thing, jumped at the chance. The show proved a showcase for her to write dramatic music with catchy tunes. Parts of the waitress’s experience were easy for her to conjure—she had waited plenty of tables before finding a label. She was also homing in on the fictional counterpart to whom she seems to naturally relate: a woman who, as she puts it, is “at a moment of reconciling the person she thought she would become with the person she actually was.” As the title character sings as she begins her affair, “It’s a bad idea, me and you. Let’s just keep kissing till we come to.”

“Waitress” opened on Broadway in 2015, and at least some reviewers seemed surprised at what it had achieved. A critic for the Times conceded that Bareilles’s music was “appealing.” Audiences loved the show, and Bareilles’s score went on to earn four Tony nominations as well as a Grammy nomination. When, in 2017, the much admired star of the production—Jessie Mueller, who had beaten Bareilles out for the Cinderella role in “Into the Woods” several years before—left, Bareilles stepped onto the stage. When the news broke, the box-office sales went up more than a million dollars in a single day—Bareilles’s fans hadn’t forgotten her. She continued to try new things anyway. The next year, she played Mary Magdalene, another conflicted figure, in a live production of “Jesus Christ Superstar” on NBC, and a few years later took the lead role in “Girls5eva,” the comedy on Peacock. The show, which she knew she wanted to do as soon as she was offered the part, can be read as a sort of gesture of disdain, a wink at the performer she would never be trapped into being. But it also gave her a new, ironic way to play with audience expectations about who she had grown up to become. At the end of the first episode, coming off the brief revival of the girl band, Bareilles’s character lies curled up on the living room couch with her husband, head on his chest. When he suggests that they celebrate, she looks briefly intrigued. “Wanna start ‘The Americans’?” he asks. Beat. She emits a hard-to-transcribe noise of disappointment, then she says, “Sure.” Resignation, love, and sense of entrapment play across Bareilles’s visage as he clicks the remote. The moment reveals another aspect of Bareilles that no one suspected: that she was an adept comic actress with an expressive face. She grew to have some of the most mobile eyebrows in the business.

In 2017, Lear deBessonet, the artistic director of the Encores! series at City Center, saw “Waitress” and loved it. When she was planning a production of “Into the Woods,” she thought of Bareilles for the Baker’s Wife. Casting Bareilles in a Sondheim musical might at first seem a daring choice: Sondheim’s sophistication was nothing she had shown before; the pie-making waitress in “Waitress” would have little to say to the pie-making madwoman of “Sweeney Todd.” But deBessonet was interested in a different aspect of Bareilles’s skills. “ ‘Jesus Christ Superstar’ and ‘Waitress’ revealed what a theatre creature she is,” she remembers. “Honesty in acting is a little bit different in musical theatre. It’s not a naturalistic theatre, and honesty in musical theatre does not equal naturalism. Her ability to locate that is so special.” Although the Baker’s Wife is not the largest or showiest part of “Into the Woods,” she may be the most important—everyone else circles around her, and she has to be played with complexity. When I spoke to James Lapine, who wrote the book for “Into the Woods,” he told me that, though neither he nor Sondheim knew Bareilles’s acting work before, “I am a huge fan of hers now, and I think Steve would be, too. She’s simply terrific as the B.W.”

Musicals in the Encores! series are not fully staged productions, and they only run for a short time. “The fact that it was a two-week commitment made it very easy,” Bareilles says. “I was, like, this will be fun. It will be a challenge.” On the downside, there was very little time to get ready. “I didn’t panic until I got to rehearsal,’ she remembers. “I just felt like I don’t want to make an ass of myself and be the only one holding a binder. But we managed.”

To help her manage—remembering her last experience with Sondheim—she turned to Andre Catrini, a New York composer and voice coach and self-proclaimed Sondheim nerd who was married to her old U.C.L.A. friend Kidwell. “If you have any question about anything Sondheim has ever done, Andre knows it by heart already,” Bareilles says. Together they sank their teeth into the role. Bareilles doesn’t read music, but Catrini wasn’t worried about that. “With Sara, it was never about how to sing the notes,” he says. They focussed on the meaning of the lyrics. Bareilles remembers working hard on enunciation. Enunciation is less important in pop music—the listener can always play the song again—whereas lyrics, as Sondheim pointed out, are often heard only once by the theatregoer, so they have to be crystal clear. Breathing, too, is famously tricky in Sondheim. As we sat, Bareilles sang me her solo song, “Maybe They’re Magic,” snapping her fingers quickly to capture the speed with which the lyrics come at the singer: “There are rights and wrongs and in-betweens. No one waits when fortune intervenes.” She opened up her voice: “And maybe they’re . . . really . . . magic, who knows?” She explained, “To be able to support that phrase, you have to fill your lungs up somewhere, and it’s not on the page.”