Role Model released his third album, Chuck Timely & The Hourglass, at midnight on August 7, 2026, hours after sitting down with Jimmy Fallon on The Tonight Show for his first televised interview — and promptly removing the host from a phone-based enemies list he has been keeping for reasons he has not entirely explained. Billboard

The 29-year-old singer, born Tucker Pillsbury and raised in Maine, told Fallon that Fallon was the most recent name added to the list — for laughing at the name "Tucker Pillsbury." The list, kept in the Notes app on his phone, has also included People magazine, MTV, and, at one point, Charli XCX. Charli XCX has since been removed and, in Role Model's words, is now in his good books. Fallon got the same treatment during the visit to NBC's studios, which aired late Thursday, August 6. Billboard

The album is a follow-up to 2024's Kansas Anymore, which was later expanded into a longer edition called Longest Goodbye. Role Model told Billboard that Chuck Timely & The Hourglass is essentially a concept album: he wanted a character to represent themes about time and the feeling of it slipping past. The record reflects a two-year stretch in which he was single while his friends were getting married. Billboard

The album includes the previously released single "High Hopes 3000," which reached No. 94 on the Billboard Hot 100 — the chart that ranks the most-consumed songs in the United States each week across sales and streams. Another track from the Kansas Anymore era, "Sally, When the Wine Runs Out," entered Billboard's Alternative Adult Airplay chart in 2025, which tracks radio play on adult-alternative stations. The new album's closing track, "Harmony," got its television debut on the Tonight Show, with Role Model backed by a chorus of vocalists in chambray shirts and blue jeans. Billboard

He also brought his mother on stage during a performance of "Sally, When the Wine Runs Out" (YouTube), and released an official lyric video for a track called "Chuck's Mantra" on his YouTube channel the same day (YouTube).

Before his own headlining run, Role Model opened for Gracie Abrams on her The Secret of Us North America tour during fall 2024 and select 2025 dates. He told Billboard the supporting slot changed the trajectory of his career. "We love Gracie," he added. Billboard

The Chuck On Tour world trek, announced in June, begins its North American leg on September 9, 2026, in Bend, Oregon, with Samia opening (Pollstar; Universal Music Canada). The tour runs into 2027.

Role Model is also set to appear on screen next year, starring alongside Natalie Portman and Mark Ruffalo in the theatrical film Good Sex. Billboard

For a singer who keeps an enemies list on his phone, the release week has been mostly about making peace — with a late-night host, at least, and with a pop star who once made the cut. The album, the tour, and the film role add up to the busiest stretch of his career so far.