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Last summer Tucker Pillsbury,<\/strong> 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.<\/em> He was the most homesick he\u2019d ever been in his life, he tells me while tugging on a gold chain around his neck that reads \u201cMom.\u201d Three and a half years into a very public relationship (and his first relationship ever)\u2014one that was hard launched<\/a> in GQ<\/em>\u2014with arguably the most influential woman on the internet<\/a>, Emma Chamberlain,<\/strong> he found himself frequently visiting home, seeking some semblance of normalcy. \u201cI was just instantly happier,\u201d Pillsbury tells Vanity Fair.<\/em> \u201cThen I\u2019d go back to LA and just sit there and go back to my sad little life\u2026It\u2019s 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?\u201d<\/p>\n 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 \u201cmay women rule the world,\u201d 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,<\/em> which is out Friday. \u201cI seriously was considering, What am I doing in my life?\u201d he says. \u201cVery much having a crisis.\u201d The album\u2019s title is a nod to the film The<\/em> Wizard of Oz.<\/em> (\u201cI\u2019ve seen it once and I don\u2019t 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,\u201d he says.) Pillsbury was searching for a way home, a way back to himself.<\/p>\n It wasn\u2019t 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.<\/p>\n 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\u2019s Instagram DMs after seeing her on TikTok to tell her that her \u2019fits were fire. Pillsbury\u2019s first album, Rx,<\/em> 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 \u201cDie for My Bitch\u201d and \u201cMasturbation Song.\u201d He found himself completely consumed by the relationship. \u201cYou just sort of disappear off the face of the earth\u2026and you make that person the center of your universe, which is romantic,\u201d he says. \u201cBut it puts these blinders on you.\u201d<\/p>\n Of course, when he was writing Kansas Anymore<\/em> last year, he didn\u2019t 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. \u201cI just wasn\u2019t present [anymore],\u201d he admits. Suddenly at a crossroads, he could feel his relationship slipping out from under him, but he kept writing. \u201cWe\u2019re hanging on by threads \/ And I can\u2019t hold it any harder on my end,\u201d he confesses on \u201cOh, Gemini,\u201d a song not-so-subtly named for Chamberlain\u2019s 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\u2019s father taught him. From the brazen breakup anthem \u201cDeeply Still in Love\u201d to the earnest, somberly nostalgic \u201cFrances\u201d (which is Chamberlain\u2019s middle name), the album chronicles the full spectrum of heartbreak.<\/p>\n With the record\u2019s obvious nods to his famed ex, Pillsbury knows that the internet will try to extract intimate details about his relationship from his music, but he tries not to think about that. He\u2019s ready to move on from his role as a famous person\u2019s boyfriend, something he was once insecure about. \u201cI will say this: Once we started putting out these singles, I fully started feeling like my own entity again, which is all I wanted,\u201d he says. \u201cThat was the biggest weight off my shoulders.\u201d<\/p>\n Beginning in September, Pillsbury will join forces with sad-girl-pop powerhouse Gracie Abrams,<\/strong> with the two going on tour and playing venues such as Radio City Music Hall. \u201cI very much thought I was done opening for people for the rest of my life\u2026but then this was just too perfect. I’m a massive fan of hers. I always have been,\u201d says Pillsbury. \u201cIt\u2019s one step closer to Miss [Taylor] Swift,<\/strong>\u201d he adds jokingly, referring to Abrams\u2019s stint as an opener for Swift\u2019s Eras Tour. \u201cI\u2019m doing the tour so that I can get free tickets.\u201d<\/p>\n In the past he\u2019s expressed his disdain for artists pedaling their music on TikTok to please their labels. For this album cycle, though, he\u2019s manufactured a digital evil twin on TikTok, Saint Laurent Cowboy, who does the posting for him. It\u2019s a satirical account, but nonetheless it\u2019s difficult to tell where the joke begins and ends. \u201cI don\u2019t know that man. I don\u2019t support him. He\u2019s trying to be me,\u201d says Pillsbury, deadpan. \u201cHe\u2019s pretending to be me, and I think it\u2019s disgusting and I\u2019ve tried to report it, but it won\u2019t work. I just say, don\u2019t follow him or engage with him.\u201d All jokes aside, he says he will oblige and post what he needs to post on the eve of his album\u2019s release before chucking his phone. But he quickly catches himself and backtracks. \u201cI\u2019ll be on my phone. Yeah, I\u2019ll be on my phone,\u201d he says, shaking his shaggy brown hair. \u201cI\u2019m very curious what people are going to think.\u201d<\/p>\n But it\u2019s not until now that he starts to consider what Chamberlain might think of the album, sinking into his seat as that reality sets in. \u201cI don\u2019t have an ounce of anger in me\u2026. I think it shows in the album; it\u2019s pretty much [me] just beating myself up,\u201d he says, as evidenced by self-deprecating songs like \u201cScumbag.\u201d \u201cI don\u2019t think it would be any news to her. I would never want to hurt someone\u2019s feelings with my music. I don\u2019t have that in my brain or heart.\u201d<\/p>\n<\/div>\n