Tucker Pillsbury said he started seeing a therapist for the first time the week before a mid-July interview about Chuck Timely & the Hourglass, his third studio album. The singer known as Role Model said the record pushed him to look inward while he was finishing work on songs shaped by dating, self-discovery and moving on from heartbreak.
“It’s going well. I don’t know if once a week is enough for me,” he said. “I feel like since I’ve got 30 years of sh*t I’ve got to start dealing with, I need more therapy.” He was 29-year-old and speaking from his home in Los Feliz, Los Angeles, with the album set for Aug. 7.
Chuck Timely & the Hourglass
Pillsbury said making the album and writing the songs led him to self-discovery. “There’s a lot of self-discovery through mindlessly dating or intentionally dating,” he said, adding that the project made him question how much he actually has it all figured out. “The album did something very good for me in the way that it made me look at myself a little bit deeper and question how much I actually have it all figured out.”
That is the practical shift in this story: the therapy began before the album reached listeners, and the record’s subject matter was already pushing him toward a more active read on his own life. For a reader following Role Model as a performer who has often turned romance into material, the new detail is not just that he wrote about change but that he started responding to it in real time.
Sally, When the Wine Runs Out
He also said he did not feel pressure to follow up the viral success of “Sally, When the Wine Runs Out.” “I weirdly did not feel pressure,” he said, though he added, “I love ‘Sally,’ and I’ll be performing that till I’m in a wheelchair.” He described the song as simple on the page, saying it “could have been written by a 5-year-old, especially the bridge, which is the most famous part.”
That mix of self-awareness and detachment helps explain the album cycle around him. The song brought onstage cameos from Hilary Duff, Olivia Rodrigo, Kate Hudson and Robert Irwin, but Pillsbury’s comments suggest the next phase is less about chasing that moment than about the work that got him into therapy in the first place. The remaining question is what specific experiences from dating and self-discovery ended up on Chuck Timely & the Hourglass when it arrives on Aug. 7.
