Role Model Enters a New Era with Chuck Timely & The Hourglass

ROLE MODEL announced his third studio album, Chuck Timely & The Hourglass, on May 28, 2026, alongside the release of its lead single, “High Hopes 3000,” which arrived on all platforms on June 3, 2026. 

Following the success of Kansas Anymore (The Longest Goodbye), an era that helped define ROLE MODEL’s sound, Chuck Timely & The Hourglass feels like a natural next step for the singer-songwriter. In an interview with Rolling Stone, Pillsbury shared that he doesn’t want to limit himself to pop or country, instead enjoying the freedom to blend the two genres. That balance remains at the heart of the album, giving Chuck Timely & The Hourglass a sound that feels familiar while still pushing him somewhere new.

The album opens with “Chuck’s Mantra,” a deeply personal, a cappella, gospel-like track that sets the atmosphere for the album, one filled with loneliness, desperation, and the search for something genuine. That feeling continues into “High Hopes 3000,” where Pillsbury reflects on emotional exhaustion and the repetitive cycle of searching for connection through L.A. nightlife. Moving between moments of hope and disappointment, he questions whether love will eventually find him or if he will always be searching for it. 

That search for connection continues through “Song Is All You Get” and “Chasing Midnight.” Both tracks explore fleeting encounters and one-night stands, with their guitar heavy, southern-inspired sound adding another layer to the album’s country-pop sound. While the connections may be temporary, Pillsbury finds something meaningful in the memories they leave behind and sometimes, ‘just a song’.

As the album progresses, however, Pillsbury begins to make room for something more lasting. “Love I You” and “Good Thing” mark some of the album’s most vulnerable moments, capturing what happens when loneliness begins to give way to genuine connection. “Love I You” feels almost unexpected from an artist who has spent much of the record questioning his relationship with love, with Pillsbury admitting that love songs don’t come easily to him. The track also features a playful, flirtatious, almost bar-like conversation with vocals from Pillsbury’s partner, Dakota Johnson, though he jokingly claimed the mysterious voice belonged to DJ Khaled. “Good Thing” follows with a similar vulnerability, exploring the fear of finding something healthy and wondering whether it can actually last. 

The album’s second single, “Joy,” brings a brighter energy to the project. Upbeat and catchy, it carries some of the same infectious energy found on “Sally, When The Wine Runs Out” from Kansas Anymore, offering a lighter moment without losing its emotional core.

“Service Receipt” feels like one of the album’s defining moments, capturing the emotional tension between missing someone and trying to move forward. Its country-pop sound fits effortlessly into the album while its lyrics reflect the uncertainty that surrounds Pillsbury’s relationship with love. Meanwhile, “Stain” looks back at an ex-lover from a place of personal growth, showing that moving forward can also mean refusing to return to what no longer serves you.

That growth becomes even clearer on “The Wedding.” After attending his first wedding, Pillsbury explained to Zane Lowe that the experience changed his perspective on love and made him realize that perhaps he isn’t as hopeless in love as he once thought.

Closing the album is “Harmony,” a fitting final track that sees Pillsbury coming to terms with his own definition of love. It feels less like a definitive answer and more like acceptance, a sign that he is finally becoming comfortable with the uncertainty that comes with opening yourself up to someone. 

Chuck Timely & The Hourglass is a bittersweet and vulnerable look at ROLE MODEL as he confronts loneliness, heartbreak, and his evolving relationship with love. The album leaves listeners with the question posed in “High Hopes 3000”, “Does love come around or does one come around to it?” You can listen to the album here.