In a new article from “The New Yorker,” D.T. Max investigates how Sara Bareilles has evolved beyond being a pop star, discussing Waitress and her current starring role in Into The Woods.

Sara Bareilles has a talent for finding the human center of things. She is currently starring in the revival of Stephen Sondheim’s Into the Woods. In the musical, she plays the Baker’s Wife, a part that Joanna Gleason – who played the wife when the show débuted on Broadway, in 1987 – first made famous, and that Imelda Staunton and Amy Adams later performed. It’s a role that’s passed like a crown from one talented actress to the next. In a musical that is mostly a dizzying roundelay of Grimms’ fairy tales – Jack climbs his beanstalk, and Little Red Riding Hood squares off against the Wolf – the Baker’s Wife stands out. She’s skeptical, hurt, and a bit bitter, like a character in a Paula Fox novel. She desperately wants a child, and once she has one, understandably, she wants a bigger house in which to raise him. After her wishes come true, she finds life with a baker and an infant boring, and hooks up with a prince, then sings of her sort-of regret. She is the relatable focus of a show where every other character is a cultural icon. “She’s messy,” Bareilles notes. “And that’s why I love her.”

I haven’t met anyone who doesn’t love Bareilles’s performance in Into the Woods. On the stage, in the show’s many ensemble numbers, Bareilles is like a human playfully hiding in a Disney World skit and, at the same time, a spritely presence peeking out in a game of guess-who’s-the-pop-star. Audiences howl with pleasure. Her sound, in a cast gifted with extraordinary voices, is remarkable. You can pick her out among all the amazing singers – the slightly earthier mezzo-soprano timbre and the soaring notes when she opens things up, a bit of pop fizz seeping from under the cap. Listen to her delicate stop-and-start argument with herself in her apologia of the tryst, ‘Moments in the Woods’.

A Tony nomination seems a strong possibility. But, whether that comes to pass or not, Bareilles, who is forty-two, will doubtless stay an unusual sort of bisected celebrity. For pop listeners now moving into their thirties, she’ll remain best known as the singer-songwriter of two monster hits, ‘Love Song’, from 2007, and ‘Brave’, from 2013. She will forever be the slightly angsty girl with the long brown hair hatching earworms from her piano: “I’m not gonna write you a love song / ’Cause you asked for it / ’Cause you need one.” And: “You can be amazing. You can turn a phrase into / a weapon or a drug.” You know you remember them.

But there was always another side to her. During those years, Bareilles was often compared with Taylor Swift, another singer-songwriter bringing a similar message to the mass market: that sensitive young women would no longer be suckers. ‘Love Song’ and ‘Brave’ went triple platinum. During a video interview at the time of ‘Love Song’, with the Daily Mirror of London, the interviewer asked the hot new singer to describe her musical style. “Piano-based pop soul, I guess,” Bareilles answered, in a voice so soft you have to lean in to hear it. Her chestnut hair was in braids, and she wore a flowery shirt. She was twenty-eight but looked younger.

She says now that this was not really her. She never truly yearned to be a pop star: “My first record came up next to Katy Perry, and it’s, like, a totally different thing. I’m not that interesting in that way,” she says. “I’m not that interested in being that interesting. I mean, there’s nothing to see.” She wanted to open up to different creative challenges and invitations. She has written the score for a Broadway show and starred in a sitcom. But she also continues to put out increasingly complex albums. As the Baker’s Wife sings after her tryst, “Why not both instead? There’s the answer, if you’re clever… Is it always ‘or’? Is it never ‘and’?”

As a result, Bareilles has stealthily made her mark in more varied ways, burrowing into more vital places in the culture than Apple Music’s Pop Hits Radio. Before her performance in Into the Woods came her work as the songwriter for the musical Waitress, which ran for more than fifteen hundred performances. It’s the story of a woman who’s abused by her husband and finds solace in baking. The sitcom Girls5eva, created by the team behind Unbreakable Kimmy Schmidt, pokes inventive fun at one-hit-wonder girl bands. She recorded her most recent album, ‘Amidst the Chaos’, in 2019, with the storied producer T Bone Burnett. Many of the tracks are comments on the contemporary political hailstorm – one song was a response to the #MeToo movement, and another was about Trump’s anti-immigration policies. None of the singles, the Los Angeles Times noted, charted on Billboard’s Hot 100. “I’m not on the radio in the same way that I was, but it’s opened up a lot of doors in terms of who I get to make things with.”

Bareilles can now sometimes walk unrecognized down a New York City street. We are meeting for drinks at Fig & Olive, a restaurant in the Meatpacking District, near the studio where she is working on postproduction for the live-capture film of Waitress. I see a smallish woman in a green-and-white striped knit top and overall shorts with a black-and-tan dog, and she introduces herself: “Sara.” Her hair is pulled back from a center part. She looks like a Tribecan who has wandered north, maybe with her yoga mat. We sit at an outdoor table so Louie, a cavapoo, can wander around a bit, and she orders a Tito’s Martini “with a twist – make it extra cold, please.”

She begins the story of her “evolution,” as she phrases it, while she sips her Martini. It turns out that she literally comes from the woods: her father and uncle both worked in the logging business, in Eureka, California, the town where she was born in 1979. Her mother and a sister did community theatre. In grade school, she started to sing and write songs for fun. She went to UCLA, where she sang in an a cappella group called Awaken. Another member of the group, the actor Geoffrey Kidwell, remembers that Bareilles took him aside and played him part of a song on the piano that she had already been working on for several years called ‘Gravity’.

Bareilles is an avid oversharer on social media. From Instagram, I learned that she takes half a tablet of medication daily for depression and anxiety, and often feels insecure. From Twitter, I know that she cried during Up. She finds the American Buddhist nun Pema Chödrön inspirational and uses the Ten Percent Happier app. In 2020, after she redeployed a vision board as a tray on which to rest some pizza dough before she slid it onto a pizza stone, she posted this takeaway: “Hold on to your dreams and then remember it’s ok to let them change and maybe use them to make other dreams come true. Like pizza.”

What is perhaps less well known about Bareilles is how hard she has always worked. While they were both students at UCLA, Kidwell once came upon her at a café, entering a list into her planner and then putting a line through each item, and, when he asked what she was doing, she explained. “I really like the feeling of accomplishing things. So I’m writing down things I already did and then crossing them out.” During college, she played local spots: a kosher Chinese restaurant called Genghis Cohen, the Hotel Cafe, Westwood Brewing Company; she also played private parties. “She would just gig and gig and gig and gig,” Kidwell said. One performance had an audience of only twelve people, all friends.

The effort paid off quickly. The band Maroon 5, some of whose members were friends of hers from college, asked her to open for them. Then a self-produced album, ‘Careful Confessions’, in 2004, began to get a following for Bareilles, and she caught the eye of a manager. A year later, she was signed to a major record label. Immediately, Bareilles intuited that she had made a mistake – in her memoir, “Sounds Like Me,” she says that the first thing she did was lock herself in her bedroom and cry. She worried that “the big, bad pop monster would eat me,” she says in her book. Soon she felt the intuition confirmed, as the label assigned her various songwriters who didn’t understand her sensibility.

In frustration, she wrote ‘Love Song’ – both her break-out hit and, because of how it came to be written, her claim to authenticity. The story of the song’s origin is usually told as the label literally demanding a love song from her for the album and receiving this sputter of rage instead. Bareilles says that the defiance was not that specific; she felt that the label wanted a style of pop she didn’t want to create and wrote ‘Love Song’ as a sort of general eff-you gesture. (She admits in her book that she may have had a role in perpetuating the more dramatic version of events but has since tried to correct the record, to little avail. “I just remember getting exhausted by trying. It was just too long-winded,” she explained to me. “Like, eventually, you’re just, like, ‘Yeah, that’s fine. It’s just not exactly true.’ ”)

Either way, the song’s meta trick – a woman writes a catchy tune about being unwilling to write a catchy tune about love – gave the song permission to succeed both as protest anthem and marketable totem. The gambit seems obvious now, and possibly a little cynical, but Bareilles says that it came from a deep ambivalence. She adds that her manager and label, after hearing the album, called “Little Voice,” were both surprised by how successful it was. “And it’s an interesting thing,” she reflected now, fiddling with the rim of her Martini glass, “as someone who struggles with self-esteem to be, like, did we all not believe in me a little bit?”

‘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, “The 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 The 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 “The 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 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 UCLA 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 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 UCLA 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.”

By the time the show opened at City Center, Bareilles had mastered the role. And when it moved to Broadway two months later, her performance, especially her comic skills, stood out. “Bareilles’s performance as the Baker’s Wife has only grown, beanstalk-like,” the Times applauded. Brian d’Arcy James, who plays her husband, the Baker, recounted to me a time when he worked with Bareilles on how she should convey her impatience with his character’s dithering. She came up with an idea to pull his apron string in irritation and tried it out one night. “She just yanked it, and it got a really big laugh,” James says. “She’s not afraid to take chances in front of fifteen hundred people in a theatre.”

For some singers, the experience of being the acclaimed star of a Sondheim production would finally define them – even ‘Moments in the Woods’ ends with the Baker’s Wife seeing the virtue of the familiar – but that is not the case for Bareilles. The show has been extended for eight more weeks, into October, but she is leaving after 4 September to get back to her album. “I had put off making a record,” she explains. “This opportunity came. I was, like, OK, well, I can push it off a little bit. But making the transition into writing is not an overnight thing. It’s going to take a minute, so I’m just taking a little space.” She says that she is just at the beginning of the new album: “Generally, I like to go back to voice memos and demos that have accumulated over the last few years and see if anything sticks. But, for this record, since I really haven’t been doing much writing, I think I might be starting from scratch.” First she will go to Vancouver, where her boyfriend, the actor Joe Tippett, is working on a television show.

She remembers her assignation with Sondheim happily. “I don’t think I really appreciated the complexity of it, and the craft of it, until I was, like, looking at it from the inside,” she says. She turns aside to call for Louie to come back, and, when I ask her whether there’s another Sondheim role she’s eager for, she pauses. “I just don’t know them well enough to name,” she says, adding, “There are many things I’m a late bloomer in.”