“Music has always been at the center of everything with my family,” says Chelsea Cutler. The 27-year-old singer-songwriter grew up here in Westport, where she says “there was always a soundtrack” of artists like Bob Dylan, Bruce Springsteen, or the Rolling Stones playing, while she and her family were eating outside, spending time at Compo Beach, or taking their small boat out on the water. While in high school (she attended boarding school), Chelsea started making her own music, but it wasn't her only focus: she went on to Amherst College to play soccer. During her junior year, a pivotal moment came when she was offered a spot touring with Quinn XCII, and she decided to leave and pursue music full-time. She credits her parents, whom she says moved to Westport partly because they were drawn to the artsy spirit in town, for supporting the move, even when it seemed non-traditional compared to her peers. “Growing up in a place like Westport, you have all the resources to live up to the pressure, and education is really important to my family,” she says. “Leaving [Amherst] was weird. But my parents were kind of the ones who encouraged me to do it. They saw a chance and they were like, you should go do that while the iron’s hot.” And hot it was: Her first album, How to Be Human, was released in 2020, and since then, she’s released 2021’s When I Close My Eyes and last year’s Stellaria. Her songs are evocative, combining precise storytelling with rich production and catchy hooks that have resonated with fans: How to Be Human hit no. 23 on the Billboard 200, she was named to Forbes’ 30 Under 30 music list in 2022, she’s amassed nearly 400K followers on Instagram, and the lead single from Stellaria, “Your Bones,” exploded on social media. “[My songwriting] is a product of who I’ve grown up listening to,” Chelsea tells Westport Lifestyle. She points to other influences like Coldplay’s Chris Martin—whose lyrics she says “always feel applicable, no matter what you’re going through”— and The 1975 and Bon Iver, who focus on specificity and intimacy. “I’ve fallen in love with both styles of writing,” she says.
Through this unique songwriting process, Chelsea has developed a reputation for being “brave” in her songwriting, particularly in her honesty about her mental health, but she says she doesn’t see her lyrics that way. “I don’t think about being an advocate for mental health at all,” she says. “When I’m feeling a certain way, I like to put it out into art. It’s just kind of a byproduct that it translates as mental health visibility. When I’m in my New York City studio [apartment] making an album, I’m not thinking about hundreds of thousands of people hearing these lyrics. I’m just like oh, what does this mean for me in the moment?”
Of course, hundreds of thousands of people do connect to Chelsea’s music: she’s performed sold-out shows in iconic venues like the Ryman Auditorium in Nashville and Radio City Music Hall in N.Y.C. “Performing is my favorite part of the job by a mile,” she says. “Being face to face with people lets you connect in a way that’s so much more meaningful [than online]. I love everything about it— from living on a tour bus to traveling to the fan interaction element.”
On July 27th she’ll be headlining right here at home, in a special show at the Levitt Pavilion. “I’ve actually never been to a show there— I have no idea what to expect!” she says with a laugh. “But I think it will be really fun.” And when she’s back in Westport, she plans to take full advantage, visiting her hometown favorites, like Rizzuto’s (“During the pandemic, I was with my parents, and we ate at Rizzuto’s so much they know our dog’s name!”), Compo (“The beach is the best, I love to watch the sunset there”), and the Sherwood Diner (“The diner’s my spot. I try to go every day when I’m home”).
Summer in Westport is always special. But Chelsea’s show is sure to make it even more so.
July 27 at 7 p.m. at the Levitt Pavilion for the Performing Arts, tickets start at $31.75, buy at levittpavilion.com