Who Is Chuck Timely? Role Model Explains—Sort Of
With the release of his new single and video “High Hopes 3000,” the artist starts a new chapter with a new alter ego.
Role Model’s new era is taking things back in time. The retro-tinged new music video for “High Hopes 3000,” the first single off his forthcoming third studio album, Chuck Timely and the Hourglass, arriving August 7, sees the singer leaning into the titular character—a jean-jacket-wearing slacker mechanic who’d rather be rollerskating around town than dealing with his curmudgeonly boss.
So who is Chuck Timely, exactly? It’s a question fans have been asking since Role Model, aka 29-year-old musician Tucker Pillsbury, launched a mysterious Instagram account this spring featuring shots of himself as the character popping up in the background of important moments in pop music history. In one black-and-white picture, he’s hanging with Paul McCartney and John Lennon during the Abbey Road recording sessions. In another, he’s mugging with Britney Spears and an old Mac computer in the ’90s.
When asked to explain Chuck’s identity, Role Model plays it coy. “Oh, he’s a legend,” he tells W of the character. “From the stories I’ve heard, he’s been around through all the eras and seems to grab little pieces from each along the way. He’s been around forever. He’s in the ‘High Hopes 3000’ video, and he’ll be on stage every night.”
Role Model on the set of the “High Hopes 3000” video.
The “High Hopes” video, shot in the quaint Hudson Valley town of Piermont, New York, is the first introduction to Role Model’s next chapter. His sophomore album, 2024’s Kansas Anymore, included the career-defining track “Sally, When the Wine Runs Out,” which quickly became both a fan favorite and a cultural juggernaut. An A-list array of “Sallys,” including Natalie Portman, Olivia Rodrigo, Kate Hudson—and, during his October 2025 SNL performance, Charli xcx—have jumped onstage during his sold-out tour stops to play the titular character.
“‘Sally’ taught me a lot,” Role Model says of that song. “The whole album did, but with ‘Sally’ I felt like I found a really great world for my voice. I pulled inspiration from a lot of my favorites for that song, and it’s cool that it resonated in such a pop way. Made me really excited to go and do it with some more knowledge and style.”
A similar feel-good, sing-along, all-American rock vibe permeates “High Hopes,” which Role Model performs in the video with a charming, devilish grin, cigarette dangling in hand. The video moodboard included “a weird mix of Footloose and Punch-Drunk Love,” he says. “With some grease on it. For the song itself, it was a little bit of everything. I wanted the keys from some of my favorite Hall & Oates and Doobie Brothers songs blended with some Georgia Satellites. Basically, if you put a cowboy on a yacht, but float it down a dirty little river in Pennsylvania.”
While the Chuck Timely Instagram is filled with images of old cassette tapes, Role Model clarifies: “I’m not old enough to be a cassette kid. My mom put me on to great music at a young age, but I was stealing music on my iPod.”
It’s possible Chuck Timely will travel beyond the analog era anyway. “The common thread throughout was this idea of time and my relationship with it,” he says. “I felt the pressure of it in a lot of ways, but I won’t get too specific yet.”
Until then, audiences can sit with “High Hopes 3000,” whose lyrics capture the specific, good-natured flavor of yearning Pillsbury has been known for since he first adopted the cheeky Role Model moniker in early 2017. He’s enjoying the opportunity to play a whole new character with Chuck.
“It makes it really fun for me to separate myself from it,” he says of performing under different names. “Like, I write the music and open myself up to the world and spend so much time hyper-focused on myself and how I feel, or how I see the world. So it's nice to be able to hide behind something afterward and have fun.”
