Role Model (Tucker Pillsbury) resisted his label’s push to collaborate with established producers for his new album Chuck Timely & The Hourglass, choosing instead to work with Mason Stoops and Taylor Mackall, who previously contributed as session musicians on his 2024 album Kansas Anymore.
After the breakout success of his single “Sally, When the Wine Runs Out,” which reached No. 1 on the Billboard Hot 100, the label encouraged Pillsbury to capitalize on the viral moment by pairing with major producers. “My label was like, ‘You want the big dogs. This is your chance to have those huge producers in the room,'” Pillsbury told Apple Music’s Zane Lowe. He said he had to “fight it for a little bit” before convincing them to proceed with Stoops and Mackall, whom he believed had untapped talent for producing pop music.
Pillsbury described the album’s songwriting process as largely improvisational, with many sessions beginning without fully formed songs. The standout track “Good Thing” came together in roughly an hour after the musicians began jamming without a plan. “They literally just started playing, and then we were like, ‘Wait, this has kind of got like a Willie [Nelson] vibe to it,'” Pillsbury said.
Chuck Timely & The Hourglass is set to be released on August 7, 2026, and includes the previously released single “High Hopes 3000,” which debuted at No. 94 on the Billboard Hot 100.
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- Aug 7, 2026 — Thompson’s Point, Portland, Maine · Get tickets
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Source: Billboard







