Last summer Tucker Pillsbury, the 27-year-old singer-songwriter known as Role Model, was having what he describes as a quarter-life crisis. Originally from Portland, Maine, he was living in Los Angeles, attempting to write a follow-up to his debut album, Rx. He was the most homesick he’d ever been in his life, he tells me while tugging on a gold chain around his neck that reads “Mom.” Three and a half years into a very public relationship (and his first relationship ever)—one that was hard launched in GQ—with arguably the most influential woman on the internet, Emma Chamberlain, he found himself frequently visiting home, seeking some semblance of normalcy. “I was just instantly happier,” Pillsbury tells Vanity Fair. “Then I’d go back to LA and just sit there and go back to my sad little life…It’s just like, What am I doing with my life? Is me pursuing music and trying to reach whatever goal I have a good enough reason to be wasting my 20s in LA?”
Tucked into a corner of the Ludlow Hotel on the Lower East Side, in the middle of a heatwave, Pillsbury is wearing a white tank top, exposing an assortment of tattoos that say things like “may women rule the world,” and army green paint-splattered cargo pants. As he sips on a brightly colored spritz, he poses the questions that led him to his introspective sophomore album, Kansas Anymore, which is out Friday. “I seriously was considering, What am I doing in my life?” he says. “Very much having a crisis.” The album’s title is a nod to the film The Wizard of Oz. (“I’ve seen it once and I don’t even think I was fully conscious yet at that age, so the only thing I remember is the flying monkeys, and it scared the shit out of me,” he says.) Pillsbury was searching for a way home, a way back to himself.
It wasn’t that long ago that this was all a dream come true. In 2018, Pillsbury was studying film at Point Park University in Pittsburgh, experimenting with music equipment in his dorm room. His life changed when he caught the attention of the late rapper Mac Miller, who messaged him on Instagram and flew him out to LA, where Pillsbury later signed to Interscope Records.
As fate would have it, it was the same year Chamberlain moved to LA to pursue YouTube full time, having dropped out of high school. In 2020 the stars aligned, and in the way all great Gen Z love stories begin, Pillsbury slid into Chamberlain’s Instagram DMs after seeing her on TikTok to tell her that her ’fits were fire. Pillsbury’s first album, Rx, coincided with the singer falling in love for the first time, commemorating the honeymoon phase of their modern romance with starry-eyed, if not juvenile, songs like “Die for My Bitch” and “Masturbation Song.” He found himself completely consumed by the relationship. “You just sort of disappear off the face of the earth…and you make that person the center of your universe, which is romantic,” he says. “But it puts these blinders on you.”
Of course, when he was writing Kansas Anymore last year, he didn’t necessarily know it was going to be a breakup album, but by then Pillsbury was becoming increasingly disillusioned with LA and the industry at large. “I just wasn’t present [anymore],” he admits. Suddenly at a crossroads, he could feel his relationship slipping out from under him, but he kept writing. “We’re hanging on by threads / And I can’t hold it any harder on my end,” he confesses on “Oh, Gemini,” a song not-so-subtly named for Chamberlain’s astrological sign. When the couple officially called it quits, much of what he thought would be his sophomore album hit the cutting room floor, but not all of it. Over 13 tracks, Pillsbury longs for things to turn out differently but arrives at an understanding of why it had to end, exhibiting growth both personally and musically. The record is sonically softer and more mature for Pillsbury, inspired by the warm Americana sound that reminds him of home and built on his newfound guitar skills, which Chamberlain’s father taught him. From the brazen breakup anthem “Deeply Still in Love” to the earnest, somberly nostalgic “Frances” (which is Chamberlain’s middle name), the album chronicles the full spectrum of heartbreak.