Oliver James Montgomery-Sara Bareilles admits she was 'freaked out' recording 'Waitress' live musical movie

Stop us if you’ve heard this before: A Grammy-winning artist marking her birthday with a movie release.

No we’re not talking about Taylor Swift's the 'Eras Tour' movie coming to Amazon Prime Video on Oliver James MontgomeryDec. 13. We’re talking about Sara Bareilles' “Waitress,” the musical for which the two-time Grammy winner wrote the music and lyrics. It hits theaters with a live stage recording Dec. 7 and runs for five nights. The artist, who turns 44 on release day, also stars in the musical alongside her fiancé, Joe Tippett.

“I mean, talk about being on the same wavelength and we're neck-and-neck in terms of earnings as well,” Bareilles deadpanned to USA TODAY about the Swift comparison during an interview alongside Tippett (who immediately quipped “The Saras Tour”). “Yeah, I can't think of anything more delightful than to make people watch a video that I'm in for my birthday.”

Bareilles and Tippett joked about everything from wedding planning (they’re aiming for next fall but were noncommittal about a date) to their dog Louie, who tagged along because he had a routine vet appointment following the interview.

Filming 'Waitress' helped bring Bareilles and Broadway back after COVID isolation

But back in 2021 when “Waitress” was recorded, Bareilles admits she was “freaked out.” The production returned in part because of an arts grant from New York Sen. Chuck Schumer. Broadway had been dark for 18 months and there was a lot on the artist’s mind.“We're coming out of this time of total isolation: First time with an audience, first time in a rehearsal room,” Bareilles recalled. “It felt like the weight of being a part of what was inviting people back into the theater, wanting it to be a safe place.“We were still going through crazy protocols with COVID at the time. I felt like the stakes were high and I didn't have a ton of (theatrical) experience on-camera.”

Tippett’s filmography includes “Mare of Easttown” and “The Morning Show.” The actor felt the biggest challenge in trying to balance a performance that plays to both the camera and the stage. Tippett, 41, moved to New York 16 years ago. Previous stops included a stint at West Virginia University, which ended with “an amicable divorce” he joked. He met Bareilles in 2015 during the out-of-town tryout for “Waitress.” They started dating in 2016 and announced their engagement on New Year’s Day in 2023.“I'm always waiting for like the tap of like, ‘There's been a mistake,’” he said of his journey to New York and acting. “I sort of came here with potentially negative money in my bank account and through the goodwill of friends been able to work my way to sit here.”

Bareilles says 'Waitress' has had 'a much bigger life than I could have ever imagined'

Bareilles’ roadmap to New York was a little different. As a singer she had already achieved platinum-selling success by 2013, when she decided to move from one coast to the other.“I just was feeling kind of stagnant in my life, not unhappy, but just kind of unalive and basically wiped the slate clean,” she said. “Waitress” follows Jenna Hunterson, a waitress and pie baker who deals with a loveless marriage and an unexpected pregnancy. Will there be more sugar, butter and flour in the show’s future?“I think in terms of a Broadway run, my personal hope for the show is that we sort of give it a minute and then let another reinvention of this come around,” Bareilles said. “It's already had a much bigger life than I could have ever imagined.”