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The Joy, Panic, and Pathetic Charm of Modern Dating: Role Model’s Chuck Timely & The Hourglass Reviewed

5-star triumph, balancing gospel builds, country-rock pivots, and standout track "love I you" to explore the frantic chaos of modern singlehood.

Tucker Pillsbury has built a career out of wearing his neuroses on his sleeve, but on his third studio album, Chuck Timely & The Hourglass (out via Interscope Records), the American artist reaches an entirely new level of artistic clarity. Anchored by the conceptual alter-ego “Chuck Timely”, a persona Pillsbury recently described in Rolling Stone as “a little bit pathetic in a charming way”, the 13-track record explores the chaotic spectrum of being single in your late twenties: the freedom, the frantic dating, the wedding-invitation anxiety, and the existential panic of wondering if love will ever actually fix what’s broken inside.

The album opens like a solemn gospel service with “Chucks Mantra,” setting the stage with an almost magical, festive build-up. Swelling keys and choral harmonies lead the charge before delivering the haunting centerpiece line: “Time is no friend of mine.”

That tension immediately explodes into danceable desperation on “High Hopes 3000.” Driven by an upbeat, driving rhythm, the track creates a brilliant contrast between its infectious beat and its lonely lyrics (“brand new shirt, it’s a little expensive… I go out on the town trying to change my night”). It is the ultimate anthem for line-dancing through a breakdown in a packed bar.

The undisputed jewel in the crown, however, is “love I you.” Serving as the album’s emotional high-water mark, the track perfectly captures the awkward, tongue-tied sensation of falling head over heels. It balances raw vulnerability with sharp songwriting, capturing that rare sweet spot where romantic fear turns into pure, dizzying magic.

Throughout the project, Pillsbury wrestles with the rollercoaster of adult singlehood, from the warm, desert-hued single “Joy” to the mellow, country-swing sway of “Chasing Midnight” and the acoustic heartbreak on “song is all you get”(“sometimes a song is all you get”).

Ultimately, Chuck Timely & The Hourglass works so brilliantly because it never pretends to have all the answers. It is an album that captures the dual thrill and horror of watching everyone around you get married while you wonder if your turn will ever come, or if being single is just your forever normal. As Pillsbury prepares to take these songs across North America and Europe on his CHUCK ON TOUR, one thing is certain: Chuck Timely might be a little pathetic, but Role Model has never sounded more triumphant.

4/5
★★★★☆
Highly Recommended

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