Role Model has spent much of his career turning emotional awkwardness into an art form. On Chuck Timely & The Hourglass, his third studio album, Tucker Pillsbury takes that instinct somewhere considerably stranger: into the past, through the mechanics of time travel and, apparently, straight into the life of a charmingly pathetic grease monkey named Chuck Timely, whose particular superpower seems to be making questionable decisions across multiple eras. It’s a suitably absurd vehicle for an artist whose best songs have always found humor and vulnerability in the uncomfortable spaces between romantic idealism and real-world disappointment.

Chuck Timely & The Hourglass is built around an elaborate retro aesthetic, with Pillsbury treating the album rollout like an artifact recovered from some alternate timeline. He sent vintage-style “acquaintance cards” to fans and created a dedicated Instagram account for Chuck, taking the character beyond a marketing gimmick. It all gives the album a world of its own, one where the past isn’t simply a visual style but a central obsession.

Musically, Pillsbury is moving forward by going back. His familiar plainspoken songwriting and emotional candor remain intact, but they’re buoyed by folk-pop and alt-pop arrangements that give the songs a looser, more adventurous personality. The album’s themes are appropriately timeless: aging, regret, nostalgia and the fantasy that one could simply rewind the clock and make a different choice. But rather than treating those ideas with solemnity, Pillsbury filters them through Chuck’s oddball mythology, finding something funny in our universal desire to bargain with the past.

That idea is what makes Chuck Timely & The Hourglass more than a clever concept record. Beneath the vintage props and time-travel mechanics is a very contemporary question: If you could go back and fix everything that went wrong, would you really want to? Role Model doesn’t need a time machine to answer it, he’s using the album instead. Chuck Timely may be stuck somewhere in the past, but Chuck Timely & The Hourglass sounds like Role Model figuring out where he wants to go next.