Role Model on Making Music He’s Proud of and Viral Sexiest Man Campaign (Exclusive)

Oct. 29 was a day of defeat for Role Model. The results of PEOPLE’s Sexiest Man Alive 2024 Readers’ Choice Poll were in, and despite the singer-songwriter’s tireless campaign — which included T-shirts, billboards and an assist from Gracie Abrams — he’d lost the title of sexiest musician to Harry Styles.

A TikTok posted to his satirical burner account, Saintlaurentcowboy, conveyed his disappointment; in a video viewed 3.3 million times, the singer (né Tucker Pillsbury) pointedly ripped in half a shirt that featured a Photoshopped Sexiest Man Alive cover with his face on it.

Dec. 10, though, was a new beginning for Pillsbury and PEOPLE, as the singer, who this year won over a legion of new fans with his heartfelt second album Kansas Anymore, was named one of our Ones to Watch.

“I think we squashed the beef. I’ll take you off my enemies list,” he says with his signature deadpan humor, as he insists his ardent campaigning was hardly just a schtick. “[But] that was not a bit. That was my entire life.”

Such dedication — be it to a joke, to a cause or to his music — is par for the course with Pillsbury, 27. Kansas Anymore, which came out in July, marked a more mature sound for the star, who ditched the electronic synths of his earlier releases for ‘70s-inspired guitars and banjo. The softer direction accompanied equally earnest lyrics, most of which found Pillsbury struggling to make sense of his breakup with social media star Emma Chamberlain last fall after three years of dating.

“[Music] was brand new [to me] when I first put out a song, and I think people got to watch me very slowly figure it out,” he says. “I think Kansas Anymore was the turning point, where I just figured all my s— out. It was finally an album that I’m proud of and that I genuinely listen to all the time.”

Though he says he had “no expectations” upon releasing the album, which follows his 2022 debut Rx, Pillsbury was “truly blown away” by the positive reaction. He was also relieved that the music stayed front and center, as he knew his vulnerable lyrics would be heavily scrutinized by fans searching for clues about his personal life in the wake of his very public breakup.

“I will say that was one of my biggest fears, because it happened a lot with my first album, and a lot of it was about [connecting it to my relationship] and almost none of it was about the music,” he says. “And then it felt like a switch with Kansas Anymore, where the music was finally good enough to overshadow the fact that people might link certain lyrics to certain people or whatever. I think it was finally more about the music than the tea of it all.”

Discovering a passion for music came later in life for Pillsbury, who was born and raised in the small coastal town of Cape Elizabeth, Me. His mom loved Jackson Browne and Van Morrison, but his dad mostly listened to A.M. radio, and music wasn’t a huge part of his childhood. His first concert was the Jonas Brothers with his mom, who bought the tickets because Nick Jonas was a Type 1 diabetic, and Pillsbury had recently been diagnosed himself.

He enrolled at Point Park University in Pittsburgh with the goal of becoming a filmmaker. But after someone who lived on his dorm room floor introduced him to songwriting and production, he quickly fell in love.

“I skipped class for a week and was just like, hyper-focused on this,” he recalls. “I always loved writing and poetry, and it got me to do a weird new type of writing. I was like, ‘Oh, this is so amazing. I have things to say.’”

Pillsbury started making songs of his own, cold-calling local venues around Pittsburgh asking if he could open for any upcoming shows. Before long, his 2017 song “Stolen Car” caught the attention of Pittsburgh native Mac Miller, who had his manager reach out.

“I was on the verge of stopping [music] because I was failing school for two years at that point,” he says. “I was just about to really quit. I gave myself a window, and somewhere in that window he hit me up and then flew me out to L.A. to meet Malcolm. That’s when it started.”

And as for the stage name, he jokes now that he’s “kind of mad” about it, as it started as an ironic joke about his not-exactly-admirable behavior.

“I urge any rising artist to just really think about the name you’re going to choose, because if something works, then you’re stuck with that name for a while,” he quips. “It was funny at a certain point, and now it’s my name and people will call me Role and it’s the weirdest thing ever.”

Being recognized in public may still be strange to Pillsbury, but it makes sense considering his social media presence, which often consists of deadpan jokes and booty-shaking. His TikTok videos have an off-the-cuff air that leave fans feeling like they’ve been let in on private posts meant only for his inner circle.

The star admits that his tendency to lean into the bit could have a deeper meaning — but he’s not overthinking it.

“I feel like I turn everything into a bit in my life. I think that’s my way of dealing with things and keeping myself grounded,” he says. “I don’t know. I’m not a very serious person, but maybe if I really wanted to analyze it and go therapy mode, maybe it is some sort of coping mechanism. Who knows? It’s like, what’s the problem? I don’t know. I love the way my brain works.”

Pillsbury is fresh off the end of a European tour, his first headlining show in two years. This past fall, he opened for Gracie Abrams, an experience he calls a “full-circle moment,” as he’s a longtime fan of the singer-songwriter. In February, he’ll kick off the North American leg of the tour.

He jokes that every tour prior was just him “holding a microphone and running around the stage.” He’s more musical now, though, playing guitar on most songs as he banters with the crowd.

“I’m just excited to hear all the girlies screaming the songs,” he says. “I’m in a much better headspace in my life, so I’m able to be more myself online and around the music. I also finally have an album that I’m very proud of and that I love and listen to. I’m glad it took this long. I think I’m finally starting to figure it out.”