December 10: A New Beginning
For Pillsbury and PEOPLE, Dec. 10 marked a new beginning. This year, with his heartfelt second album Kansas Anymore, he won over a legion of new fans. He says with his signature deadpan humor, "I think we squashed the beef. I’ll take you off my enemies list." He insists his ardent campaigning was not just a schtick. "That was not a bit. That was my entire life."Music as a Journey
Such dedication, whether to a joke, a cause, or his music, is typical of Pillsbury, who is 27. Kansas Anymore, released in July, marked a more mature sound for the star. He ditched the electronic synths of his earlier releases and embraced '70s-inspired guitars and banjo. The softer direction was accompanied by equally earnest lyrics, mostly about struggling to make sense of his breakup with social media star Emma Chamberlain after three years of dating.He recalls, "Music was brand new when I first put out a song, and people got to watch me slowly figure it out. Kansas Anymore was the turning point where I finally figured everything out. It was the first album I'm truly proud of and listen to all the time."
Although he had "no expectations" upon releasing the album following his 2022 debut Rx, he was "truly blown away" by the positive reaction. He was relieved that the music remained the focus as he knew his vulnerable lyrics would be closely examined by fans searching for clues about his personal life after the public breakup.
Discovering a Passion for Music
Discovering a passion for music came later in Pillsbury's life. 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 significant part of his childhood. His first concert was with his mom to see the Jonas Brothers, as 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 a dorm mate introduced him to songwriting and production, he quickly became passionate. "I skipped class for a week and was hyper-focused on this. I always loved writing and poetry, and it led me to a new type of writing. I realized, 'Oh, this is amazing. I have things to say.'"
Pillsbury started making his own songs and cold-called local venues in Pittsburgh asking to open for shows. Soon, his 2017 song "Stolen Car" caught the attention of Pittsburgh native Mac Miller, who had his manager reach out.
Stage Name and Public Recognition
Regarding his stage name, he now jokes that he's "kind of mad" about it as it started as an ironic joke about his behavior. He quips, "I urge any rising artist to think carefully about the name they choose. If something works, you're stuck with it for a while. It was funny at one point, and now it's my name, and people call me Role, which is the weirdest thing ever."Being recognized in public may still be strange to him, considering his social media presence with deadpan jokes and booty-shaking. His TikTok videos have an off-the-cuff feel that makes fans feel like they're part of 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. It's my way of dealing with things and staying grounded. I don't know. I'm not a very serious person, but maybe it's a coping mechanism. Who knows? I love the way my brain works."
Pillsbury is just ending a European tour, his first headlining show in two years. Last fall, he opened for Gracie Abrams, an experience he calls a "full-circle moment" as he's a longtime fan. In February, he'll start the North American leg of the tour. He jokes that previous tours were just him "holding a microphone and running around the stage." Now, he plays guitar on most songs and banters with the crowd.
"I'm just excited to hear all the girlies screaming the songs. I'm in a much better headspace in my life, so I'm able to be more myself online and around the music. I finally have an album I'm very proud of and love. I'm glad it took this long. I think I'm finally starting to figure it out."