Up to this point, Role Model’s career has been dominated by a single question: “Where’s my Sally tonight?”
All of last year, during live performances of his breakthrough song, “Sally, When the Wine Runs Out,” the singer would shout out those words before bringing out a special guest to sing (or really, chant) the bridge with him. The nightly Sally started out as a lucky fan, plucked from the crowd, and later (as is the custom of the times) graduated to celebrity cameos including Charli xcx, Natalie Portman and Bowen Yang. The live bit helped turn the catchy, country-leaning single about a one-night stand into a viral sensation.
But beyond the benefits brought by the success of the song, the silly, sun-drenched melody of “Sally” also helped the 29-year-old, whose music had already gone through multiple evolutions, figure out the musical direction of his next project.
“I learned about what a bridge can be,” Role Model, whose real name is Tucker Pillsbury, tells NPR. “I just wanted to take what I learned from that production and what could be considered a pop radio song and then go do much better versions of that.”
So he built his third studio album, Chuck Timely & The Hourglass (out Aug. 7 via Interscope), around one cardinal rule: no synths and no programmed drums. Pillsbury says he listened to a lot of Madonna and yacht rock while conceptualizing the record, but he forced himself to think about how to emulate the feeling of the music without reaching for the obvious sounds.
“I liked having a rule,” Pillsbury says. “It’s like, how do we get the danciness of these ’80s synth pop records within our palette?”
The result is a collection of jangly piano-and guitar-driven melodies fit for a dive bar jukebox. Often rowdy and loose — like the Georgia Satellites-infused lead single, “High Hopes 3000” — and at other times lovelorn and downtrodden, Chuck Timely sounds like a 21st-century approach to heartland pop: an amalgamation of roots and Americana references with the modern sensibility of a songwriter who knows how to craft a social media hit.
Pillsbury says the title character of the album came to him about halfway through the writing process.
“A lot of the songs are about time in a very general sense, but the passing of time, maximum nostalgia — wanting to go back in time and change things about myself or relationships,” he explains. “I’m now at this place in my life where friends are getting married or having kids, moving away, moving on with their lives. I was single for two years and just feeling very stagnant, so I wanted [Chuck] to represent that feeling.”
He created a vision board for the time-traveling Chuck, which included Paul Newman aviators, Repetto shoes and “kind of pathetic, drunk, but also charming male loneliness.” Sonically, he tapped into an adult contemporary sound that plucks inspiration from artists including Jackson Browne, Bruce Springsteen and Bruce Hornsby, grounding the album in blue-collar grit with enough bouncy bridges to create TikTok earworms.
“I love Americana, and I think there’s so many cool ways you can bring it into pop music,” he says. “I love that challenge.”
Originally from Maine, Pillsbury attended film school in Pittsburgh and quickly found himself more invested in the music scene than in his classes, shooting and directing videos for local artists. Eventually, someone lent him recording equipment and he started uploading songs to Soundcloud. He was immediately hooked, but couldn’t convince his parents to let him drop out to pursue music. He released his debut EP, Arizona in the Summer, in 2017, a collection of brooding, understated songs produced in his bedroom. Soon after, Pillsbury got a message from the manager of rapper Mac Miller: The Pittsburgh native — who had started out making goofier songs in high school, but by that time had grown into moodier, more ambitious compositions — was a fan of the lo-fi track “stolen car” and wanted to get in the studio together.
“I’m not a religious man, but that was like a moment of God at the perfect time. They flew me out, I got to meet Malcolm and work with him,” Pillsbury says, referring to Miller by his given name.
Their collaboration never officially saw the light of day, but it helped put Pillsbury on the path that led to signing with Interscope in 2018. As Role Model, he continued down a spiky, alt-pop route until his second full-length album, 2024’s Kansas Anymore, pivoted into rock and folk textures. The softer sound mirrored the lyrics, which chronicled the end of his high-profile relationship with influencer Emma Chamberlain. Making that change, Role Model says, better suited his voice and his ability to write music — and it kicked his career into high gear.
In February of 2025, Role Model released the deluxe version of Kansas Anymore, which included “Sally” as a bonus single. The song quickly became his biggest hit to date. GQ writer Chris Black anointed him the male equivalent to some of today’s main pop girls: Sabrina Carpenter, Chappell Roan and Gracie Abrams. (Role Model supported Abrams on tour last year; her breakout single, “That’s So True,” was also a bonus track on the deluxe version of her 2024 album. Essentially, “Sally” flew the same path a matter of months later.)
As the “Sally” phenomenon was taking off, Pillsbury was already working on what would become Chuck Timely. He put the album aside to star in the upcoming rom-com Good Sex, written and directed by Lena Dunham, before returning to the studio. Pillsbury says he knew by then that he’d cracked the code to his sound, so he wasn’t worried about delivering on his follow-up to his hit song.
“There is no pressure. Because as much as I love ‘Sally,’ that bridge could have been written by a five-year-old,” he laughs. “Like, those lyrics are not good. ‘Cold like Minnesota, hotter than a fever’ — it’s ridiculous. I’m glad it worked, and I love that song for what it is, but I also knew myself and knew that I had grown even just by the time that song came out.”
He sparked online hype and ran with it, but he was already thinking about where to go next. On Chuck Timely & The Hourglass, Role Model takes the barroom sound that worked so well on “Sally” a step further. The arrangements here are more intricate, swooping across late-night confessions and endearingly sloppy pick-up lines. Pillsbury’s voice shines brightest when he hollers or lingers on a note until it sounds like it might crack. To Chris Black’s point, he has carved out a lane for himself as one of today’s most visible male pop stars. Not quite Harry Styles and not quite Noah Kahan, Role Model sits somewhere in between: a tattoo-covered, acoustic guitar-slinging frontman who relies on real instruments to write songs about his situationships. (His rumored girlfriend, the actress Dakota Johnson, makes a flirty appearance on the bridge to the bluesy “Love I You.”)
At a moment when country music is ruling the charts, it would be easy to fully hop on the trend, go all-in on pedal steel and heartbreak. Role Model’s musings on modern dating manage to subvert musical expectations, swerving into new terrain when things start feeling too predictable. On the smooth sailing “Stain,” he details a gutting phone call from an ex that stirs up old wounds. His voice floating through breezy keys and flute harmonies, he lets the sting roll right off his shoulders. Pillsbury credits his producers, session musicians Mason Stoops and Taylor Mackall, for steering him in the right direction, as on the song “Chasing Midnights,” when they made intentional choices to keep it from crossing too far into folk or country territory, even though the song itself seemed a natural fit for the genres.
“It really screamed for banjo and screamed for a fiddle solo in the bridge,” Pillsbury says. “We were just like, what’s the opposite of those things to bring it in? And so we did a flute solo where a fiddle probably should have been, and we did a sitar instead of a banjo.”
Pillsbury will celebrate the release of the album with a special homecoming concert in Portland, Maine, before hitting the road this fall on his biggest headlining tour yet.
“We grew the band for this, which I’ve wanted to do forever, but that costs a little extra money,” Pillsbury says, smiling as he rubs his thumb against his fingers.
The “Sally” bit has come to an end — no more special guests, no more nightly anticipation over who gets pulled onstage. Role Model proved he can create a viral moment and milk it, but now he wants to show he can deliver a timeless experience.
Copyright 2026 NPR
