It’s official: Role Model has updated his enemies list.
Things are moving along nicely for the singer and songwriter. He opened for rising star Gracie Abrams in 2024 and 2025. The 29-year-old is set to star alongside Natalie Portman and Mark Ruffalo in the theatrical version of Good Sex (after the Netflix romcom of the same name), due out in cinemas next year. His new album, Chuck Timely & The Hourglass, dropped at midnight. And, to promote it, he stopped by The Tonight Show Starring Jimmy Kimmel for a live performance from Chuck Timely, and his first interview with the late-night show’s host.
With fame, comes haters. For some years, Role Model has kept a list of enemies close to his heart – or at least, in his pocket, on his Notes app.
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It started with People magazine, he told Fallon. MTV has graced its pages. So has Charli XCX (for a curious reason. She’s now in his good books). Fallon was on the list. He was the last person added to it, punishment for laughing at Role Model’s real name — Tucker Pillsbury.
With his visit to NBC’s studios, which aired late Thursday, Aug. 6, Role Model has cleared Fallon’s name. Phew.
The introspective Chuck Timely & The Hourglass includes the previously released single “High Hopes 3000,” which hit No. 94 on the Billboard Hot 100, and serves as the followup to 2024’s Kansas Anymore (Role Model is from Maine, by the way). An extended, “Longest Goodbye” version of Kansas Anymore carried “Sally, When the Wine Runs Out,” which entered Billboard‘s Alternative Adult Airplay chart back in 2025 and remains one of Role Model’s biggest songs to date.
Chuck Timely is, essentially, a concept album. “I wanted to have this character to represent the themes on the album,” he tells Fallon. “A lot of it is about time and time passing. And I was in this two-year period of being single and my friends were getting married…” And, well, here we are.
During his debut stint on the couch, Role Model recounted how he got the call to support Gracie Abrams on her The Secret of Us North America tour during the fall of 2024 and with select dates the following year. It was an instant “yes,” and the experience “went on to, like, change the trajectory of my career,” he recounts. “We love Gracie.”
Role Model also stuck around for the TV debut of “Harmony,” the closing track on his new LP, with support from a chorus of backing vocalist, all dressed in chambray shirts and blue jeans.
Watch the performance of “Harmony” below. And stream Chuck Timely & The Hourglass in full.
