Role Model, whose real name is Tucker Pillsbury, has released his third album following the viral success of “Sally, When the Wine Runs Out.” Despite his love for the song, he recognized the need to move beyond it. During live performances, Pillsbury would engage the crowd by asking, “Where’s my Sally tonight?”
This tradition involved bringing a guest to sing the bridge, starting with fans and eventually featuring celebrities like Charli XCX, Natalie Portman, and Bowen Yang.
The lively performances helped turn the song into a viral success and influence the direction of his new project. Pillsbury mentions, “I learned about what a bridge can be,” speaking about the catchy, country-leaning single.
His third studio album, Chuck Timely & The Hourglass, was developed with a clear rule: no synths or programmed drums. Pillsbury drew inspiration from ’80s synth pop without using obvious sounds. The album features piano-and-guitar-driven melodies reminiscent of a dive bar jukebox. “High Hopes 3000,” the lead single, reflects this style, blending rowdy and downtrodden tones.
The character Chuck Timely emerged halfway through the writing process, inspired by themes of time and nostalgia. Pillsbury created a vision board for Chuck, incorporating influences from artists like Jackson Browne, Bruce Springsteen, and Bruce Hornsby. These references ground the album in blue-collar grit, yet it’s contemporary enough to create social media hits. “I love Americana,” Pillsbury says, “and there are many ways to bring it into pop music.”
Pillsbury’s journey began in Maine, where he attended film school in Pittsburgh. He gravitated towards music while capturing videos for local artists. A chance opportunity to record and upload songs to Soundcloud led him to pursue a music career. His debut EP, Arizona in the Summer, caught the attention of Mac Miller’s manager, leading to a significant collaboration, although unofficial.
Role Model’s music journey evolved through genres, eventually landing him a deal with Interscope in 2018. His second album, Kansas Anymore, featured rock and folk elements, aligning with the emotional narrative following a high-profile breakup. This shift better suited his vocal and songwriting skills. The song “Sally,” included as a bonus on the album’s deluxe version, became his biggest hit, catching mainstream attention.
While working on Chuck Timely, he paused for a role in Lena Dunham’s film, Good Sex, before returning to music. Pillsbury felt confident about his musical direction. “There is no pressure,” he states, referencing the simplicity of “Sally’s” lyrics. The album elevates the barroom sound of “Sally” with intricate arrangements and emotive performances. He continues to carve his niche as a male pop star, using real instruments to tell stories.
The album Chuck Timely & The Hourglass resists predictable trends by experimenting with different musical elements. In “Stain,” Pillsbury addresses a painful phone call from an ex over breezy melodies. His collaboration with producers and session musicians adds a unique flavor, opting for a flute solo where a fiddle might naturally fit.
Role Model is set to celebrate the album’s release with a homecoming concert in Portland, Maine, followed by a significant headlining tour. His band has expanded for this project, showcasing his commitment to delivering a memorable and timeless experience. No longer relying on “Sally’s” viral success, Role Model is poised to establish his sound for the long haul.

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