As staycations go, the one Sara Bareilles took one bright weekend in August checked all the relaxation boxes: a luxury Midtown Manhattan hotel, a passel of besties bonding over drinks, the promise of spa treatments. But Bareilles’s respite also carried an echo of loss. It was orchestrated by her friend Gavin Creel, a Broadway actor who died in 2024.
“He left, in his will, very specific instructions,” Bareilles said when we met in the hushed hotel restaurant over breakfast. Along with covering the cost of the suite at the Aman New York, Creel had planned explicitly, and generously, for everything down to room service. “It’s so in his spirit,” Bareilles said, smiling. But she didn’t have time for all the accouterment. “He’ll probably haunt me, for not doing it right.”
Bareilles, the singer-songwriter who became a theater fan favorite with her musical “Waitress,” and then reinvented herself again for TV with the critically beloved “Girls5Eva,” has been haunted a lot over the past few years. Creel and another pivotal friend had succumbed, far too young, to cancer. Anxiety pinned her down more than ever before. She and her husband, the actor Joe Tippett, are struggling with infertility. This era’s social and political upheavals, including the pandemic — it all threw her for a loop. “I couldn’t get over the surreal sense of, ‘Oh, the world is not what I thought it was,’” she said.
Even as her career blossomed with new challenges — she is at work on another buzzy Broadway musical, an adaptation of the best-selling Meg Wolitzer novel “The Interestings” — Bareilles was awash in sorrow. She finally gives voice to it in “Good Grief,” her first studio album in seven years, released late last month. It’s a song cycle in 14 tracks of her signature piano ballads, plaintive or bristling about inequities. The rawness of her feelings, and the urgency of the music — which sometimes arrived to her, unexpectedly, in one rush — are palpable. “I’m having a nervous breakdown,” she announces in one tune, with a jaunty melody as counterpoint.
Those waves of vulnerability are also on full view in a documentary about the making of the album. In “Sara Bareilles: Good Grief” (in theaters), Bareilles emerges as a warm but determined bandleader, even as the crying starts about six minutes in, and ebbs only intermittently. She and the musicians tear up, hug and harmonize through recent anguishes.
After many rounds of I.V.F., Bareilles lost a pregnancy, her first, earlier this year, she told me. “It sucks,” she said, adding: “Of course I wish I didn’t have a miscarriage.” Yet she also felt a measure of “relief,” she said. This stretch of her life, “would be really, really, really hard” if she were pregnant.
The complexity of that response intrigued her. “Give it the most amount of ache you can,” she instructed her band as they recorded the elegiac but hopeful “Ladies in a Line,” which she wrote while at a fertility clinic, waiting for a blood draw.
Revealing all that, and more, could be tricky on the public stage, and Bareilles worried briefly about airing her darkest moments. “I thought I would feel really exposed, in a way that felt dangerous,” she said. But the opposite happened.
“I feel more empowered with less artifice,” she told me, as she sat, in a semi-rumpled white linen shirt and red pants, on the last morning of her staycation. (She lives in Brooklyn.) “Just telling the truth is really the only thing I’m interested in.”
BAREILLES HAD a Top 10 hit in 2007 with her debut single, “Love Song,” and another earworm six years later in the peppy, anthemic “Brave.” Now 46, she is a rarity for a (female) pop artist. At a time when many of her contemporaries hit closed doors, her theater achievements have given her a steady and welcoming outlet: “Waitress,” for which she wrote the music and lyrics and in which she eventually starred, received four Tony Award nominations in 2016; Bareilles later earned a Tony nomination for her performance in a revival of the Sondheim musical “Into the Woods,” and a Grammy for the cast album. Her songwriting on “Girls5Eva,” about a washed-up girl group aiming for a comeback in their 40s, garnered an Emmy nomination in 2024. “The Interestings” is set to premiere early next year at Berkeley Rep, with an eye on Broadway.
“She’s had success in a variety of forms, and when you’re up close working with her, you see why,” said Aaron Dessner, the in-demand producer (Taylor Swift, Brandi Carlile) whom Bareilles enlisted to help her finish “Good Grief.” “She’s a timeless artist.”
Bareilles, who also won a Grammy in 2020 for best roots performance, for her slow-boil “Saint Honesty,” is clear-eyed about her place in the mercurial music business. “I’m not cool enough,” she said evenly. But, she added, because of the “artistic world that has built up around me and that I’ve helped create, I don’t feel as much like I have anything to prove.”
Her friend and “Girls5Eva” co-star Renée Elise Goldsberry observed, “She has this beautiful humility and confidence at the same time.”
For “Good Grief,” her seventh studio album, Bareilles gave the core musicians points and producer credits — a way to counter the industry’s financial contractions. Ahead of her tour, which begins on Sept. 9 in Boston, she held a series of free pop-up performances that were, essentially, grief-ins. “I’m grateful for the invitation to cry in public,” she said in the documentary.
Once Bareilles found the LP’s theme, she saw its universality. The soaring opening song, “Home,” was inspired by a conversation between Anderson Cooper and Stephen Colbert, who spoke about losing their fathers in boyhood on Cooper’s podcast, “All There Is.” Bareilles played “Home” for Cooper on another episode; by the end he was crumpled, weeping with his face in his hands.
To be able to dwell in that heartbreak — your own or others’ — and channel it, into what Dessner called “compositional depth and just raw vocal ability,” is part of Bareilles’s gift, her collaborators said. (“I learned a lot from her,” Dessner added.)
Glennon Doyle, the podcaster and author, invited Bareilles to be a fellow producer on “Come See Me in the Good Light,” the Oscar-nominated documentary about the poet Andrea Gibson, who died months after the film’s premiere in 2025 — another loss.
“Sara and I are both people who have stayed pretty close to sadness,” said Doyle, who is also a producer on Bareilles’s album documentary. “Or we were born with extra doses of it, I’m not exactly sure. But I think we both understand that grief is really holy ground, and that if you surrender to it, it is kind of this portal to really deep connection — to yourself, and to other people, and to whatever you call God.”
Confronting her grief was cathartic, but still agonizing for Bareilles: In the documentary, directed by Josh Alexander, she convulses with sobs about the loss of Creel, who died at 48 and whom she considered a platonic soul mate. An adored figure in Broadway circles, he played the wolf and the prince opposite her baker’s wife in “Into the Woods.”
The collaboration and narrative of theater changed her writing, Bareilles said, and Creel inspired one of the most wrenching songs on the LP, told from the perspective of “the one who’s leaving,” as she put it. Called “Forever,” it’s a blueprint for endurance for those left behind.
“The person I’m becoming because of the loss,” she said, “it’s more who I think I’m supposed to be. But I don’t know if you get there without the fire of real pain.”
Bareilles didn’t initially imagine turning her private grieving into song. When her friend and former manager Chad Joseph died in 2020, the turmoil of the Covid pandemic had left her unable to write.
Then came “Girls5Eva.” She was the first person cast, playing Dawn, the conflicted, down-to-earth leader of the group. She tried to convince Tina Fey, an executive producer, and Meredith Scardino, the creator, to look elsewhere: “I was like, are you sure?”
But leaning into comedy turned out to be “such a gift,” she said. “It was life-changing.” (A Lexapro prescription to manage the anxiety she had long suffered from also helped, she said.) Her co-stars became dear friends; several, like Goldsberry, appear in the sweet and funny video for “Still Crying,” a Patsy Cline-esque paean.
Onstage or off, Bareilles is her same unassuming, open self, Goldsberry said, with an easy intimacy. Even as an acquaintance, “you might as well have been crying with her on the phone the night before.” They leave each other long voice texts, oversharing. “Mainly, she’s just always there for you.”
GROWING UP in Eureka, Calif., a northern coastal city, the youngest of three daughters of an insurance adjuster father and a mother who worked at a pharmacy and a funeral home, Bareilles didn’t envision herself as a star. The life she made, after graduating from U.C.L.A. with a degree in communication, has been “a total surprise and delight,” she said.
In college, she joined an a cappella group, and sensed that she had found her tribe. She tuned into that feeling for “The Interestings,” which is set around a summer camp for artistic teens, and follows them into adulthood.
It’s a sprawling story and an ambitious musical, which Bareilles called a passion project. When the producers asked her to collaborate, she began writing the score even before she finished the novel.
At a Manhattan rehearsal space last month, she and Wolitzer — who is the show’s book writer along with the playwright Sarah Ruhl — continued fine-tuning the production. As Bareilles observed, with a pencil behind her ear and her ever-present dog, a Cavapoo named Louie, on her lap, one character sang about how love and dreams transform across decades.
“I think it’s about, what is a good enough life?” Wolitzer said of the new musical.
That too, is something Bareilles is sorting through, as a performer and a person.
At a recent pop-up show, a box of tissues was passed around as a capacity crowd gathered in the lobby of a theater at Lincoln Center. Fans — mothers and daughters, couples swaying hand-in-hand, college students and 60-somethings — ringed Bareilles, in a patchwork jacket, as she played a Steinway. They dabbed their eyes through the new songs and bobbed along, eagerly, to the favorites. In the quiet moments, all you could hear were sniffles.
Singing the truth is hard. “I feel like my responsibility as an artist now, as I get older,” Bareilles had said, is “to hold the nuance and the complexity in a way that feels gentle and loving.”
“I always am hoping,” she said, “that my music brings comfort.”
Sarah Bahr contributed reporting.
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