Sally, When The Wine Runs Out has shifted the direction of Role Model’s career by an astonishing amount. Not only has it become the biggest thing to sport Tucker Pillsbury’s sobriquet by a huge distance, it’s defined who he is as an artist. In his musical journey from hip-hop to bedroom-pop to the featherweight wisps of country, nothing has stuck like this one song—a little poppy, a little classic, and ripe for turning into something greater. The fact that it’s become the trigger for Pillsbury to bring out another celebrity friend at his live shows for over a year seals that firmly.
Even on a whole successive album, Sally…’s creative wine is evidently still yet to run out. After listening to Chuck Timely & The Hourglass, it feels like the linchpin representation of who Pillsbury is as an artist. Here, relayed through the eyes of his titular, time-travelling alter ego, Pillsbury embraces the gamut of what Sally… laid down wholesale. He’s small; he’s pitiable; he overshares like no one’s business; and he’s more than a little desperate. Naturally for an album about careening through single life and falling at almost every hurdle, it can make for some of the most recognisable Role Model music to date.
A big part of that comes from how much Pillsbury can bring both in and out of character. In it, he’s Chuck Timely, cool-guy barroom lothario and patron of the honkytonk and soft-rock that’s worked its way into this album’s makeup. It’s also nakedly (and deliberately) see-through. High Hopes 3000 is like if Achy Breaky Heart had not a drop of bravado to it. Later, Dakota Johnson is totally game for the flirt on Love You I, while Pillsbury sounds like this is his first time interacting with a woman. It’s almost comedic how the faceplants play out, again, with deliberate energy. It’s all in service of the final pair, The Wedding and Harmony, sticking the landing, with the realisation that happiness and love can come in their own time, at their own pace.
Of course, for as much peritextual fleshing-out that’s been dedicated to Timely as a character (he’s worked with both Michael Jackson and Olivia Rodrigo, apparently), his isn’t a voice that takes over Pillsbury’s too much. You can tell when it does, in cornball shuffles like High Hopes 3000 and Joy, or the “aww, shucks” commiseration of Song Is All You Get. At the same time, considering how reserved and boyish Pillsbury’s voice is, you’d think it would get taken over more often. As it stands, there’s something of a toothlessness to how the album is presented. The furthest extent of both broadness and introspection is quite fragmented, and the album can sag a little for it.
The production, too, sometimes doesn’t do that any favours. On one hand, you feel the spirit of Timely’s chintzy yacht-rock collection on Love I You and Service Receipt; on the other, they’re still a casualty of bedroom-pop anti-scale being applied even where it shouldn’t be. Good Thing and The Wedding might be prim and improbably clean, but their embossed strings have room to breathe and sound genuinely lovely for it. As for the flavour-drained Chasing Midnight or the gated, colicky Stain, there’s a tepidity to go along with their lack of eminence that just doesn’t impress very much. For as cheap and clanky as High Hopes 3000’s approximation of a country stomper is, at least it’s a bit fun.
Overall, though, there’s a vision to Chuck Timely & The Hourglass that you can’t say isn’t met. That’s been true of every Role Model album, really, though the extra bit of effort sunk into this one does give it flecks of its own personality that prove really valuable. Among the overall catalogue, its predecessor Kansas Anymore still ranks higher for being Pillsbury’s most successful reinvention, but the pieces of something more are beginning to fall into place here. If nothing else, there’s enough indication to believe Pillsbury’s hitmaking career hasn’t begun and ended with Sally…; there’s still plenty of room on that foundation to keep building.
For fans of: Harry Styles, Bleachers, Del Water Gap
‘Chuck Timely & The Hourglass’ by Role Model is out now on Interscope Records.
Words by Luke Nuttall
