Sara Bareilles on love, anxiety and a new film version of ‘Waitress’

Sara Bareilles on love, anxiety and  a new film version of ‘Waitress’



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As a musical theater-obsessed kid growing up in Eureka, Calif., Sara Bareilles didn’t have access to big Broadway shows.

So she can’t wait to roll out the filmed performance of her musical “Waitress,” the Broadway show for which she wrote the music and lyrics and stars as titular server Jenna Hunterson.

The musical opened in 2016, garnering four Tony nominations.

Over its five-year run, Bareilles played the pie-genius waitress several times, wowing audiences with poignantly personal renditions of her own showtunes.

The new movie version is out on Dec. 7, which happens to be Bareilles’ birthday. I

t’s a pretty amazing gift.

“I’ve written one musical in my life, so this is a really big deal, to preserve this and get to share it,” she tells Alexa. “Especially with fans all over the world who didn’t get to see it in London or on Broadway.” 

The multi-hyphenate talent joins me on Zoom from her house in upstate New York, swathed in a dark-green Humboldt hoodie (a hat tip to her home county), long brown hair in a bun.

She’s a recent, and enthusiastic, Manhattan-to-Brooklyn convert, but her upstate spot is “my favorite place on Earth,” she says. “It’s just the most incredible, tiny hole in the wall in the woods.”

Her fluffy Cavapoo, Louie, is here, too, lazily stretched out on the table next to her laptop.

Later that day, she’ll be reuniting for dinner with her “Girls5eva” castmates, Renée Elise Goldsberry, Paula Pell and Busy Philipps. (As the actors’ strike has ended only hours before our chat, we can actually talk about the sitcom’s upcoming third season!)

“Camden” jacket and “Layla” skirt, both price upon request at Adeam; “Astrilarge Botta” boots, $1,995 at Christian Louboutin; “Slim Tire” earrings, $290 at Nickho Rey Photographs by Victoria Will

At 43, Bareilles has already received an intimidating list of awards and nominations, including two Grammy Awards, three Emmy nominations and three Tony nods.

Her sixth studio album, the T Bone Burnett-produced “Amidst the Chaos,” was released in 2019 to rave reviews.

In addition to “Waitress,” she wrote a song for the 2016 “SpongeBob SquarePants” musical (for which she got one of those Tony noms); played Mary Magdalene in the 2018 NBC live performance of “Jesus Christ Superstar”; and scored another Tony nomination for her run as The Baker’s Wife in the recent revival of “Into the Woods” on Broadway.

Fans of Bareilles, and people who know her personally, love her a lot.

I encounter this sentiment over and over while researching her: She’s the nicest, the most down-to-earth.

There’s an audible comfort in her voice, even in the kind of soaring melodies she often performs — the challenging compositions of Stephen Sondheim, particularly.

Composer Andre Catrini told Vulture that Bareilles’ vocal range “doesn’t seem to have a break, which is insane.

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She goes from the depths of her chest to her mix and her soprano with total seeming ease.”

From left: Busy Philipps, Renée Elise Goldsberry, Sara Bareilles and Paula Pell in “Girls5eva.” Heidi Gutman/Peacock

“I don’t work so hard at singing,” Bareilles concedes. “It feels very natural. I do think that I got lucky.”

But she’s made a name for herself by being absolutely herself in everything she does.

“I don’t really have the poker-face thing,” she says. “I didn’t get that gene. So I don’t have a great capacity for presenting something that’s not truthful.”

This commitment to radical honesty yielded two of her biggest hits: “Love Song,” a clapback at being told by music execs to write a swoony ballad, and “Brave,” an ode to coming out, whose chorus exhorts the listener to “say what you wanna say.”

Through her stage and screen roles over the past several years, there runs a theme of creative, messily imperfect women striving for something more — and learning to appreciate what they’re good at.

It’s a sentiment Bareilles channeled in writing her belt-it-out solo number in “Waitress.”

“She Used To Be Mine” is about looking back on the bravado of youth with an affectionate, wistful eye. 

“When I started writing the show,” she reflects, “I had just moved to New York from Los Angeles. I had just left a relationship of six years. I left my manager, I left my band. I felt really unmoored. So the idea of a woman who has this moment of reckoning, like, ‘How did I f–king get here?’ I felt really resonant with that.”

Coat, $2,998 at Lafayette 148; “Bubble” earrings with amethysts and pearls, $175 at Ileana Makri Photographs by Victoria Will

“Waitress” and (the formerly Peacock, now Netflix show) “Girls5eva” both center around women’s stories in still-unusual ways.

“Waitress” made history as the first Broadway musical with a team of four women in the top creative positions.

“Girls5eva” is an ensemble piece that, minus the laugh track, harkens back to the glory days of the genre: It revolves around a chart-topping girl group, a la the Spice Girls, reuniting in middle age for a second go at fame.

Growing up, Bareilles says, “my favorite shows were ‘The Golden Girls’ and ‘Designing Women,’ these wonderful ensemble shows. Meredith Scardino, our showrunner and creator, and the collaboration with Tina Fey and Robert Carlock — they’re just heavyweights in comedy. Making these women feel real and ridiculous at the same time — I think it’s not an easy feat.”

“Tar” cropped jacket, $1,550, and ball skirt, $2,695, both by special order at Bach Mai; “Bow” heels, price upon request at Versace, 747 Madison Ave.; Prasi Dois Irmãos choker in 18-k yellow and white gold, $56,500 at Broken English Jewelry Photographs by Victoria Will

For Bareilles, “Girls5eva” arrived at a particularly heavy time: She had just lost one of her best friends.

“I needed to laugh so badly,” she says. “It was just like this medicine for my soul. I think that’s part of why this show feels so sacred to me.”

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The third season continues the group’s adventure in midlife music industry adventures — with the added physical comedy of Bareilles’ hugely pregnant prosthetic belly.

We talk about the relationship between trauma and comedy, about how humor can be one of the most primal, life-affirming forces.

That’s a balance that runs deeply through “Waitress,” which manages to be both a lovely, sexy and breezy comedy — acrobatic actor Christopher Fitzgerald’s number “Never Ever Getting Rid of Me” is a highlight — and a harrowing look at an abusive marriage.

That, too, is not an easy feat.

“Tonally, it really crosses a huge divide,” she says. “It’s part of what I love about the show. Because I think life is so wild like that.”

The musical’s source material, the 2007 Adrienne Shelly-directed movie, also ably navigated these themes — then fell under a very dark spell when Shelly, who also starred in the film as the quirky waitress Dawn, was murdered shortly before the film’s release. 

Charity Angel Dawson, Sara Bareilles, Amanda Kloots, Caitlin Houlahan and Christopher Fitzgerald during the curtain call at “Waitress” on Broadway as the musical re-opens on Broadway after the pandemic shutdown. Bruce Glikas/Getty Images

“I did a lot of talking to Adrienne, inviting her into my process,” Bareilles recalls. “It was my greatest hope that we would make something that we thought she might be proud of. It wasn’t like, ‘Fix this thing.’ It was like, ‘Preserve this beautiful jewel that she created.’”

In the musical film, Bareilles’ real-life fiancé, actor Joe Tippett (“The Morning Show”), plays Earl, the abusive husband.

To inhabit the polar-opposite world of Jenna and Earl, the couple enlisted an intimacy coach.

“We would do what they called tapping in and tapping out,” she says. “We would look into each other’s eyes, take a deep breath, kind of enter our character space. And then at the end, we would make sure to connect, take a breath, give each other a hug. Try to leave that world behind. To be honest, I’m glad not to be in that dynamic anymore. We’re better and healthier.”

The abuse storyline has evoked an emotional response from audience members.

“We’ve gotten incredible letters from people who have left painful relationships, or made decisions about their lives, that feels very much tied to watching this woman’s story,” Bareilles says. “And that’s an incredible piece of why it feels important to share on a larger scale.”

Brandon Maxwell “Louise” top, $2,595, and “Jade” button up, $1,295, both at Moda Operandi; Brandon Maxwell “Clover” shorts, $2,995 at Saks Fifth Avenue; Enchanted Forest chain double ring (Bareilles’ right ring finger), $85 at Anabel Aram; “Baroque Pearl Coil” ring (Bareilles’ left ring finger) in 14-k yellow gold with diamond and pearl, $538 at Grace Lee; “Felipa” boots (shown in top photo), $480 at Castaner Photographs by Victoria Will

Sharing is a central aspect of Bareilles’ brand.

She’s been open on social media about her struggles with depression and anxiety, which in recent years led to her starting anti-anxiety medication.

“When the pandemic happened, some bottom dropped out for me, and I was really very unable to cope,” she says.

Like many artists, she worried that medication would dull her creative spark.

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But she’s found it to be the opposite: “What I have in my pocket now is this unbelievable capacity for joy.”

She’s become a cheerleader for others who are similarly struggling.

“I always say this to people who are nervous to try it: ‘You can always come back to doing it this way. Right?’ Might as well try another tool and see if it helps.”

It was Tippett who nudged her to try medication.

“He was like, ‘You have to try something else; this is not working.’” Bareilles describes their relationship as a zesty one that necessitates leaning into the uncomfortable moments — and the inevitable clashes from two creative people in a partnership. “It’s like alpha dogs pissing all over the same territory,” she says with a laugh. “Like we’re just not interested in acquiescing, at times.” 

This is not to say it isn’t fun.

“There’s so much good stuff there. Joe is the right partner for me. He’s incredibly kind and loyal and very funny; he has this huge appetite for life and history and intellect. He encourages me to expand, and sometimes the expansion is a little painful. But my therapist says this great thing about alchemy — that nothing cooks without heat.”

Jenny Packham “Marlene” cape, $4,915 at Farfetch; Satin Bullet bodysuit, $295 at Fleur Du Mal; “Simone” earrings with Swarovski crystals, $498 at Jennifer Behr Photographs by Victoria Will

She’s got another project cooking, though she can’t name it yet.

“Yeah, I’m working on a musical. Writing songs. It makes me so f–king happy. It’s about very real, feeling people. There’s no giant event. It’s just the ache of being alive, and there’s so much to say about that, especially right now.” 

I ask if she has any advice for regular people, when it comes to being musical.

Can one learn to enjoy singing even when one doesn’t have Bareilles’ chops?

“I think pursuing music, if it brings you joy, please f–king do it,” she says. “If we cannot pursue joy, what the f–k are we doing here?”


Editor: Serena French; Talent Booker: Patty Adams Martinez; Photo Editor: Jessica Hober; Stylist: Anahita Moussavian; Hair: Satoko Ichinose; Makeup: Samantha Lau for A-Frame Agency using Charlotte Tilbury; Nails: Kylie Kwok at TraceyMattingly.com using Essie; Fashion Assistants: Alex Bullock and Meghan Powers



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