Role Model Took His Heartbreak & Made Kansas Anymore

When I meet Role Model on a Friday afternoon, he seems calm for someone who just released a second album and a music video earlier that day. But in the last 12 hours, the 27-year-old singer-songwriter, né Tucker Pillsbury, has fielded congratulatory calls and texts from friends and family, including one from his mom that made him cry. (It was a photo of the dog on their porch in Maine listening to the record.) He also cried watching the live chat for “Scumbag,” in which fans complimented him on everything from entering his farmer era to the A24-level cinematography.

In person, Pillsbury is tall and lanky with black Saint Laurent sunglasses hiding his eyes and a maroon army cap over his dark hair. The patrons at Campbell & Co. — the coffee shop in East Williamsburg he frequented while recording Kansas at a nearby studio — don’t seem to recognize him as anything other than a hot, tattooed Brooklyn guy getting an iced coffee. But with this new, deeply personal “heartbreak album,” as he tells NYLON, and a national tour with Gracie Abrams beginning in September, that might soon change.

“This is the first album where people are like, ‘It’s the most I’ve learned about you,’” he says of Kansas Anymore as we walk around the neighborhood. Previously, there was the sunshine-y single “Blind,” which boasts more than 121 million streams on Spotify, and Pillsbury’s self-released 2017 EP Arizona in the Summer, after which the late Mac Miller flew him out to Los Angeles to work together. (“He [was] a one-of-a-kind human being,” Pillsbury says. “The advice he gave me in the short window I knew him, I still carry with me and think about it all the time.”) In 2022, he put out Rx, a poppy, upbeat album about falling in love; coincidentally, Pillsbury was falling in love. His relationship with Emma Chamberlain was soft-launched in the music video for “Neverletyougo,” in which Chamberlain’s face is never fully seen. They hard-launched at the Vanity Fair Oscars party. And then they hard hard-launched in a GQ cover story and photo shoot as a couple. In October 2023, reports swirled that the pair had split up.

As Pillsbury examines a lanternfly on the sidewalk, he says he knows that listeners will likely mine the lyrics of songs like “Scumbag” and “Oh, Gemini” to learn about his breakup with Chamberlain. “I have no regrets, and it’s a beautiful time in my life that I’m proud of,” he says. “I honestly never thought I would be in a relationship for three and a half years, and the fact that I was and that it was beautiful pretty much the entire time — I’m just very thankful. At the end of the day, I think the best thing I took away from it is knowing that I can do that and knowing that I can do that again at some point when I want to or when I’m ready.” (He’s dating but single.) Simultaneously, Pillsbury says Kansas Anymore explores other kinds of heartbreak. “The Dinner,” for example, represents Pillsbury’s homesickness for his Maine hometown and the East Coast, written after a series of unfulfilling interactions in L.A. “where I was just like, ‘What am I doing with my life?’ I miss my friends. I miss normal conversations,” he says.

Those realizations multiplied as Pillsbury was working on Kansas, he says, rolling another cigarette. After primarily working with men on his earlier music — which was a “cold” and “honestly miserable” experience, he says — he assembled a team of mostly women, including Lizzy McAlpine, who’s featured on the melancholy track “So Far Gone.” “Growing up, I would always go to my mom and my sister for anything, whether it was talking about a girl or crying to them,” he says. “I try to surround myself with people that feel like that, and I’m just comfortable with them. No one’s talking about football and who Jake Paul is fighting.”

Somebody with a sizable amount of laundry begins to exit the house where we’ve been sitting on the stoop, so we head back to Campbell & Co. Pillsbury has been rehearsing for Abrams’ tour for a few weeks, and we joke that he’ll be one degree of separation away from Taylor Swift. “I might just get to shake her hand. What happens when you touch Taylor Swift?” he laughs. But first, his next and last spot for the day is going to see his Times Square Spotify billboard. While he says he doesn’t think he could handle Taylor Swift-level fame, something big is on the horizon.