Last summer Tucker Pillsbury, The 27-year-old singer-songwriter, known professionally as Role Model, is going through what he describes as a mid-life crisis. Originally from Portland, Maine, he lives in Los Angeles, trying to write a follow-up to his debut album, Prescription He missed home the most in his life, he told me, tugging at a gold chain around his neck that read “Mom.” Three and a half years in a very public relationship (and his first)—a relationship difficult launch IN GQ Magazine-can discuss most influential woman on the internet, Emma Chamberlain, He found himself visiting home often, looking for some semblance of normalcy. “I just felt happier right away,” Pillsbury recalled. Vanity Fair. “Then I would go back to LA and just sit there and go back to my boring life… Like, What am I doing with my life? Am I pursuing music and trying to achieve any goals? Do I have enough reasons to waste my 20s in LA?”
Tucked away in a corner of the Hotel Ludlow on the Lower East Side, amid a heat wave, Pillsbury wears a white tank top that reveals an array of tattoos that read “may women rule the world” and army-green cargo pants. As he sips a bright spritz, he poses questions that lead him to his introspective sophomore album, Kansas too, will be released on Friday. “I was really pondering, What am I doing with my life?” he said. “A lot of crisis.” The album’s title is a tribute to the film The Wizard of Oz. (“I saw it once, and I don’t even think I was fully conscious at that age, so the only thing I remember is the flying monkeys, and they scared the hell out of me,” he says.) Pillsbury was searching for a way home, a way back to himself.
Not long ago, all of this seemed like 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 to LA, where Pillsbury later signed with Interscope Records.
As fate would have it, that was also the year Chamberlain moved to LA to pursue YouTube full-time, after dropping out of high school. In 2020, the stars aligned, and in the way every great Gen Z love story begins, Pillsbury slid into Chamberlain’s Instagram DMs after seeing her on TikTok to tell her that her ‘rage was like fire.’ Pillsbury’s first album, Prescription, coincided with the singer’s first brush with romance, celebrating the honeymoon phase of their modern romance with starry, if not childish, songs like “Die for My Bitch” and “Masturbation Song.” He found himself completely absorbed in the relationship. “You just kind of disappear off the face of the earth… and you make that person the center of your universe, and it’s romantic,” he says. “But it blinds you.”
Of course, when he was writing Kansas too last year, he didn’t necessarily know it would be a farewell album, but by then Pillsbury had become increasingly disillusioned with L.A. and the industry in general. “I just wasn’t there [anymore],” he admits. Suddenly at a crossroads, he could feel his relationship slipping away, but he kept writing. “We’re hanging by a thread / And I can’t hold on any tighter to myself,” he confesses on “Oh, Gemini,” a song not-so-subtly named after Chamberlain’s zodiac sign. When the couple officially called it quits, much of what he thought would be his sophomore album was cut, but not all of it. Over 13 tracks, Pillsbury wishes things had turned out differently but comes to understand why it had to end, demonstrating both personal and musical maturity. The record is sonically softer and more mature for Pillsbury, inspired by the warm Americana sounds of his homeland and built on his newfound guitar skills, which Chamberlain’s father taught him. From the cheeky breakup anthem “Deeply Still in Love” to the heartfelt, dark, and nostalgic “Frances” (Chamberlain’s middle name), this album captures the entire spectrum of heartbreak.
Given the record’s explicit references to his famous ex, Pillsbury knows the internet will try to extract intimate details about his relationship from his music, but he tries not to think about it. He’s ready to move past being a celebrity boyfriend, something he once felt insecure about. “I’ll say this: When we started releasing these singles, I definitely started feeling like myself again, which is all I ever wanted,” he says. “It was the biggest weight off my shoulders.”
Starting in September, Pillsbury will collaborate with sad pop group Gracie Abrams, with the two touring and playing venues like Radio City Music Hall. “I thought I wasn’t going to open for people for the rest of my life… but this is perfect. I’m a huge fan of hers. I always have been,” Pillsbury said. “It’s one step closer to being Miss [Taylor] Fast,” he added jokingly, referring to Abrams’ role as the opening act for Swift’s Eras Tour. “I did the tour so I could get free tickets.”
He’s previously expressed his disdain for artists who release their music on TikTok to please their labels. For this album cycle, however, he’s created a sinister digital doppelganger on TikTok, Saint Laurent Cowboy, who posts on his behalf. It’s a satirical account, but it’s hard to tell where the joke begins and ends, anyway. “I don’t know that man. I don’t support him. He’s trying to be me,” Pillsbury says, deadpan. “He’s pretending to be me, and I think it’s disgusting, and I tried to report him, but it didn’t work. I just said, don’t follow him or interact with him.” All joking aside, he says he’ll comply and post what he needs to post the night before the album’s release before throwing his phone. But he quickly realizes and backtracks. “I’ll use the phone. Yeah, I’ll use the phone,” he said, shaking his shaggy brown hair. “I’m curious what people will think.”
But it wasn’t until now that he began to consider what Chamberlain might have thought of the album, sinking into his seat as that reality set in. “I don’t have any anger in me…. I think that shows on the album; it’s pretty much [me] “I just beat myself up,” he said, citing self-deprecating songs like “Scumbag.” “I don’t think she’ll ever know that. I never want to hurt anyone’s feelings with my music. I don’t have that in my brain or in my heart.”
