Last year saw Role Model, one of pop’s great over-sharers, finish up shooting the new Lena Dunham movie, Good Sex. The filmmaker is, of course, no stranger to spilling the beans herself. Just imagine the small talk they made on set.
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It remains to be seen how the 29-year-old singer-songwriter – aka Tucker Pillsbury – fares in his first-ever acting gig, but the whole make-believe thing seems to have rubbed off on him. Where the Maine-born and LA-based musician’s previous two albums found him baring his soul, as he charted the boom and bust of his highly publicised relationship with internet sensation Emma Chamberlain, ‘Chuck Timely & the Hourglass’ is apparently named after a time traveller who’s knocked about with both Michael Jackson and Olivia Rodrigo.
Pillsbury has emphasised that this is no concept album. “I wrote all the songs and then came up with this Chuck thing to just represent it,” he told Rolling Stone. However he got here, at least he’s managed to step outside of himself a little. His 2022 debut, ‘Rx’, was an obnoxious alt-pop affair inspired by his romance with Chamberlain. That gave way to 2024’s ‘Kansas Anymore’, a countrified self-pity party staged in the wake of their break-up. Both records seemed to be way more about Pillsbury than their ostensible subject.
Thankfully, ‘Chuck Timely & the Hourglass’ explores singledom in a less claustrophobic manner, even if the Americana style is dialled up to the point of pastiche. Slickly produced lead single ‘High Hopes 3000’ sets the protagonist up as a wannabe optimist who’s “out on the town” and looking for love “over and over and over and over again”. The quest continues on ‘Service Receipt’, an MOR adventure in which he visits a diner and tries to pick up more than the bill.
Even when Pillsbury slips back into solipsism, as on ‘Stain’, he cleverly offsets ugly lyrics about heartache as “a stain that I never get out” with ultra-smooth muzak. With similar wiliness, he gets a little self-reflexive on ‘Song Is All You Get’, a slice of country radio bait that suggests heartache is worth it for the tunes. ‘Chuck Timely’ still has shades of self-pity (see the laconic ‘Love I You’) but Pillsbury is much better at depicting the freewheeling single life than plumbing the depths of emotion.
The result is his most likeable album yet. As country queen Sheryl Crow didn’t quite sing: a change can do you good.
Details
Record label: Polydor
Release date: August 7, 2026
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