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Role Model embraces singledom on Chuck Timely & The Hourglass

The singer’s third studio album sees him adopt a new alias and, with it, a fresh outlook on love.

Role Model embraces singledom on Chuck Timely & The Hourglass

The singer’s third studio album sees him adopt a new alias and, with it, a fresh outlook on love.

Tucker Pillsbury, Role Model and now Chuck Timely. The 29-year old singer from Maine has had a lot of aliases. First emerging into the spotlight as Role Model, Pillsbury’s debut album Rx mapped his infamous relationship with Emma Chamberlain, but it was Kansas Anymore — which documented the equally infamous fallout of said relationship — which propelled him into the spotlight. Full of breakup bangers, it was the on-stage cameos from celebs such as Troye Sivan and Olivia Rodrigo during Sally, When the Wine Runs Out that gave the singer his virality. 

Now, Pillsbury is back, this time adopting the Chuck Timely moniker. Healed from the breakup, Chuck Timely & The Hourglass is an ode to singledom in its rawest form (aside from the feature from Pillsbury’s girlfriend Dakota Johnson on ‘Love I You’, that is). Not quite a concept album, Timely is reportedly a time traveller who’s worked alongside both The Beatles and Britney Spears during his fabled career (take a look at his Instagram page), but the character came after the songs had been made according to Rolling Stone. Really, he’s just Pillsbury in a blazer.

Looking at singledom from a different angle to how he does on ‘Slut Era Interlude’ from Kansas Anymore, songs like lead single ‘High Hopes 3000’ catalog Pillsbury's wistful longing for a new relationship. Sonically, the album leans more heavily into the country influences that punctured Kansas Anymore. It’s nostalgic Americana, tinged with optimism and even a hint of Gospel on ‘Chuck’s Mantra’ — the album’s somewhat self-pitying opening affirmation. Overall, though, the album is upbeat and buoyant, aside from the recurring motif that time is, as the record's title would suggest, running out.

While ‘Service Receipt’ has a piano track somewhat reminiscent of late ’70s Billy Joel, as with all of Pillsbury’s previous discography, Chuck Timely & The Hour Glass is totally singular. From his rugged vocals, to the effortless blend of folk and indie sounds, the album proves what we all knew to be true: no one is doing it quite like Role Model. Move over, hot girl summer, it’s Chuck Timely’s world and we’re all just living in it.

Stream Chuck Timely & The Hourglass here.

Writer Lucy Wragg

7 August 2026