Role Model talks ‘Kansas Anymore’ deluxe, Maine and saying goodbye

Role Model answered the phone while pacing around a Holiday Inn Express gym. The 27-year-old singer explained that he was trying to get a workout in before his Tampa, Fla., show later that night. Born Tucker Pillsbury, the in-demand musician was about two-thirds of the way through his tour’s North American leg. While talking about his sophomore album, “Kansas Anymore,” Pillsbury suddenly lost his train of thought and, through his phone’s camera, a panicked smile takes over his typically sarcastic composure.

“Oh my God. There are fans outside the window,” said the singer, who had a hoodie draped over his shoulders, barely covering his torso of patchwork tattoos. “This is the worst place I’d ever want to be seen.”

For the remainder of the Zoom call, he avoids the gym’s windows and steers clear of the fans prowling the hotel’s perimeter. Since the release of his album last summer, the Maine-raised singer has settled into a new pocket of fame — with TikTok virality and obsessed fans around each corner. Almost every night, fans line up for hours to see Pillsbury strum his guitar, sing his breakup songs and hope to be that night’s “Sally,” a tradition where he brings a fan (or famous friend) onstage to dance with him during “Sally, When the Wine Runs Out.”

The No Place Like tour kicked off in November and it’s now nearing its tail end, with only a handful of American dates left. But before closing the curtain, he is bringing his brokenhearted acoustics and cowboy hat to L.A.’s Wiltern for two sold-out shows on Tuesday and Wednesday.

In an effort to keep the tour “exciting,” Pillsbury released “Kansas Anymore (The Longest Goodbye),” last month. It’s an extended version of his folk-driven album with four brand-new tracks. He continues to mourn a previous relationship (with internet tastemaker Emma Chamberlain), yearns for his East Coast hometown and guides listeners through his stages of grief.

Originally, he thought he struck the right ending with the bittersweet ballad “Something, Somehow, Someday,” on the record’s standard release. But with the opportunity to make a deluxe and heighten his newfound country flair, the singer realized he had a slightly more final farewell in him. He landed on “The Longest Goodbye,” the revised final track, where Pillsbury still leaves the heartbreak album open-ended — singing, “I don’t think I love you anymore / But I don’t think I’ll ever be so sure,” as his last words.

“If I were to go therapy mode on myself, I think I just don’t like firm endings in life, like hard nos or hard yeses. I don’t like the black and white of certain things. Goodbyes are very hard for me and I think happy endings aren’t always realistic. It’s better to leave things open-ended,” said Pillsbury. “I don’t know, I’m weird. I like movies where they all die at the end.”

After finishing his headlining tour in April, Role Model is heading back out to join Gracie Abrams on the Secret of Us Deluxe tour this summer.

(Neema Sadeghi)

He begins to detail his tour regimen and mourns the lack of outside time on show days — being outdoors reminds him most of home. Heard in the warm, Americana twangs that complete “Kansas Anymore,” these sounds are an ode to his upbringing in Cape Elizabeth, Maine. He longs for its cobblestone streets, the town’s red brick buildings and its surrounding pockets of nature.

“I will say I miss Maine every single day. I mean, especially being in Tampa,“ says Pillsbury, as he looks out the window, describing a grim, rainy day in Florida. “Maine is just like one of those places that has a sound. When you look at it, it’s an easy place to score as if it’s like a movie.”

When Pillsbury first started working on his second album, following his 2022 full-length debut “Rx,” he wasn’t sure which sonic direction he’d head in. “Rx” was a pop-ridden menagerie of sensationalized sexual lyrics and lovestruck melodies. His previous EPs (“Arizona in the Summer,” “oh, how perfect” and “our little angel”) teeter the line of melancholic bedroom pop and moody rap. So, for his second album, he continued to test the waters with different influences like ‘80s synth-pop and electronic music. But nothing was sticking.

“It’s hard to write to weird electronic s—. I can’t do it. I tried and when listening you didn’t believe any of it,” said Pillsbury. “Then I just started playing acoustic guitar in my living room and trying to write songs like I used to, back in the day. It felt a lot more comfortable, believable and raw.”

As he sat on his couch, strumming a newly learned instrument and figuring out what he wanted to say, he was transported to being a college student at Pittsburgh’s Point Park University. In 2017, Pillsbury released his first EP, “Arizona in the Summer,” a four-track project he recorded on the floor of his bedroom closet. “Stolen Car,” a dejected pop track off that EP, is originally what caught the attention of late rapper Mac Miller, who first aided Pillsbury in landing a record deal and jump-starting his career.

Role Model says his shows now “feel like an actual concert,” as he plays guitar for 75% of the performance.

(Neema Sadeghi)

“It’s a full circle moment for me. I didn’t fully know what I was doing [on ‘Arizona in the Summer,’] and I think some of the best music can come from that,” said Pillsbury. “With ‘Kansas Anymore,’ I was able to start these songs in my living room on a guitar, not fully understanding how to play guitar very well. I just was like, let me try and do the bare minimum in my living room and get ideas out — that worked better.”

When he first got signed to Interscope in 2018, the singer was thrown into several recording sessions where songwriters would ask him, “What’s on your mind?” or “How are you doing?” as a way to open up. He says it takes him a lot of time to warm up to people and being vulnerable like this in the studio was a challenge for his first few projects. Nonetheless, he created earworms like the horn-powered “hello!” and the hypnotic “forever&more,” which individually have around 50 million Spotify streams.

“I just remember walking out of the room and crying in the bathroom. It just f—ed with my head a lot. It just made me question why I couldn’t be [writing music] by myself,” said Pillsbury. “Why was I being set up with songwriters in the first place, especially when I got signed off of songs that I wrote myself? It’s a confusing thing that happens and it can definitely f— with your head. I think it does for a lot of artists, which is why I just wanted to go secret mode on this album.”

By going “secret mode,” he says that he was able to create one of his most sincere and mature records to date. He’s done making tunes like “Masturbation Song” off “Rx” — what he describes as a track “about pleasuring myself and trying to make it into a cute love ballad.” He’s moved onto a more sobering look into how he deals with heartbreak and homesickness.

From the soft guitar strum of “Frances,” a track where he tries to figure out where he went wrong, to the self-deprecating upbeat “Scumbag” and “Something, Somehow, Someday” where he croons about still believing they’re “meant to be,” a majority of this album paints a painstakingly clear picture of a breakup. But Pillsbury promises the feeling doesn’t translate to his live shows. He says he’s good at separating the trauma of what he was going through when writing the song from his stage performance — where all he can think about is trying not to forget his lyrics.

“When I’m looking at people in the crowd, I’m not thinking about my past. I’m not trying to relive that on stage in front of people. I just don’t want to see a bunch of people crying. I’d rather lift people up,” said Pillsbury. “So I try to do things with a smile to kind of lighten the mood. It’s probably why I’m joking in between every song. Comedic relief.”