Tucker Pillsbury has gone by many names: Dillis, Saint Laurent Cowboy, and most famously, Role Model. Now, the tour for his new concept album, “Chuck Timely & the Hourglass,” introduces audiences to the artist’s latest persona: Chuck Timely.

Role Model has described Chuck as a “time traveler,” one who has appeared at studio sessions and in the background of photos of famous artists for decades.

In an interview with W Magazine, Role Model said, “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.”

On Sept. 27, Chuck’s travels brought him to the stage at Leader Bank Pavilion, where he serenaded listeners, embraced the turbulent weather, and celebrated his homecoming to New England.

True to Chuck’s backstory, the night felt like a trip through Role Model’s personal history. In many ways, the performance was a return: to New England — where the artist grew up — and to the tour stop he’s historically considered his hometown show.

“I know we’re close to Maine because that girl’s holding a picture of my senior photo,” he said at one point. The jumbotrons immediately spotlighted an audience member in the pit holding up a fuzzy iPhone photo of a young, grinning Tucker.

Role Model’s love for Boston saturated every aspect of the show, from his Red Sox baseball cap to the lyric changes he incorporated throughout the performance. When he sang “The Dinner,” the lyrics “New England-born and raised” garnered rapturous cheers from the crowd.

“We’re really home now, baby!” he shouted in response.

The concert was also a journey into Role Model’s older discography, with numerous features from his 2024 album “Kansas Anymore” including “Superglue,” “Writing’s On The Wall,” and “Slipfast,” as well as selections from the 2025 deluxe version — “Old Recliners,” “Sally, When the Wine Runs Out,” and “The Longest Goodbye.” The audience reached a feverish pitch during the bridge of “Some Protector,” which Role Model declared was his favorite song to perform.

Even Role Model’s crowd work reflected what he’s learned from promoting past albums: The call and response in “Love I You” evoked his viral “Sally” routine, which incorporated audience members into the performance and became a beloved part of the two-year “No Place Like Tour” show run in support of his sophomore album.

But Chuck’s time travel didn’t simply lead him into his past. It also pointed him — and the audience — toward a more hopeful future.

The show opened with “Chuck’s Mantra,” an ethereal song that channels gospel choir vocals and repeats the affirmations: “I am deserving of something real / Something true, someday soon.”

The audience erupted into cheers as Role Model strolled out, silhouetted by the brilliant golden lights flooding the stage.

“I came to dance, Boston,” he declared before launching into “High Hopes 3000,” the lead single off his new album. From there, he segued into “Song Is All You Get,” an easy-listening, smooth anthem about appreciating the moment.

After “Song Is All You Get,” he told the audience, “That’s all, Boston, goodnight!”

The lights dropped, and the artist walked offstage.

But Role Model was far from finished. He reappeared moments later, laughing, and the audience erupted. From there, he highlighted favorites off his new album: he slowed down to savor a fresh chance at love and vulnerability on “Good Thing,” handed the mic off to listeners during “Love I You,” and got the last laugh on “Stain.” The artist reflected on a friend’s marriage and the newfound hope it gave him in “The Wedding,” and had the entire crowd on their feet and chanting during “Joy.”

Finally, he closed the show with “Harmony,” which tied every era Chuck has traveled through together and revealed the new perspective he’s gained: “It took forever, but now I see / It’s harmony.”

The stage set itself was noticeably minimalistic, pinning the audience’s full attention on Role Model and his five-person band. Fortunately, Role Model is a man who thrives in the spotlight. From ribbing fans about their “harsh” Boston accents to running over to the Jack Daniels logo in pursuit of a whiskey mid-concert, he kept fans entertained with his antics as well as his music.

At one point, he even hopped off the stage to join a dance circle in the crowd. “I had FOMO,” he admitted sheepishly before climbing back on stage.

Not even the howling wind or incessant rain could dampen his energy. It turns out that when he wrote “The rain don’t stop for anyone,” Role Model meant that even in the middle of a nor’easter, at an open air venue on the edge of the choppy sea, the show must go on. He joked that he’d been afraid the weather would deter audience members, but they proved him wrong.

“I almost forgot, New England’s f— tough as s—,” he said, and earned a huge cheer in response.

Fortunately, Role Model made it well worth weathering the elements. For just a few hours, Chuck Timely paused his travels through time to remind listeners that although life changes and sand is always running through the hourglass, no loneliness lasts forever.

—Staff writer Makenna J. Walko can be reached at [email protected].