Tucker Pillsbury has made a career out of being palatably quirked-up. Since his generic-brand blackbear 2022 debut Rx, Pillsbury has carved out an undeniably endearing persona as Role Model: He has a finsta! He posts photos of himself photoshopped into the Abbey Road sessions! Mac Miller discovered him! Darn it, he loves iced coffee! He wasn’t taken particularly seriously until 2024’s folksy, pouting post-breakup LP, Kansas Anymore, but what really shot him into the mainstream was that record’s deluxe-edition addition “Sally, When the Wine Runs Out,” which Pillsbury admitted in an interview featured his “dumbest lyrics.” The song went viral on TikTok thanks to its kitschy live bit: Pillsbury bringing celebrities onstage to be his nightly “Sally”: Jake Shane, Conan Gray, Olivia Rodrigo, even the Wiggles, for some reason. In the wake of “Sally,” Pillsbury has become something of an industry darling: during a recent Apple Music interview about the upcoming LP, Zane Lowe practically kissed his feet under the table. (In fairness, Lowe does that with almost everyone.) But his third album, Chuck Timely & the Hourglass, finally sees him attempting to establish an identity as a thoughtful artist. Often oscillating between swaggering and simpering, the 12-track LP sees Pillsbury take on an alternate identity as a lonely mechanic stumbling his way through hapless, half-drunk singledom, hoping to ignore the feelings he’s developing for one lucky lady. It’s rollicking, easygoing indie pop with a silly, satisfying twang. Sure, it’s a bit lyrically rote at times—“Who’s that knocking at my door / Better be an angel, four-four-four” isn’t winning any awards—but that’s all well-hidden by bouncy, slickly produced instrumentals and Pillsbury’s winning, Maine-inflected rasp. “Song Is All You Get” is girded by sunny guitar licks and judicious synths; “Joy” is a catchy, electric guitar-forward tune with clear eighties country-rock inspiration. An impressive array of instruments (glockenspiels, banjos, sitars, 12-strings, and violins, among others) helmed by Mason Stoops and Taylor Mackall makes for a uniformly pleasing, full-bodied sound, especially on “High Hopes 3000,” the album’s bluesy, energetic lead single. In that aforementioned Zane Lowe interview, Pillsbury described making a “mood board” for the album as its first step. You can tell: Chuck Timely & the Hourglass is aesthetic-obsessed, sometimes to a fault. Pillsbury’s chosen tropes can come across as crutches. Belying his chosen sobriquet, he seems to spend an inordinate amount of time talking about drinking (he’s even swigging a beer on the album’s cover). Eight of the album’s twelve songs mention drinking, hangovers, and being at the bar. The most dramatic example is “Love I You,” an admittedly charming, jazz-reminiscent ditty about a lonely pass at a coy honey. It also features a spoken word inclusion from current girlfriend Dakota Johnson, if you’re into that. “Chuck, Chuck, Chuck, Chuck!” female voices cry as the song fades out. If you’re not listening hard, they sound like they’re yelling “chug, chug, chug.” Get it? The listener is also hit over the head with the cowboy trope: Pillsbury (as Timely) spends his time hanging with barflies, swinging women ‘round by their beltloops, banging on jukeboxes, and singing “crying cowboy song[s]” over a suspiciously limpid guitar line. He also won’t stop whooping and including claps into his instrumentals—folksy pastiches that could pass as Song Sung Blue knockoffs, the musical equivalent of an airplane movie. But Chuck Timely does bloom around its centerpieces, when Pillsbury drops his yee-haw facade to sell what he does best: blushing loverboy vulnerability. What he lacks in vocal range he makes up for in pathos; you know the love songs are good because they hurt your solar plexus a little bit to listen to. “Chasing Midnight” is an open, acoustic-driven tune about a one-night stand that’s actually quite affecting. A flute dances around Pillsbury as he sings in a gentle head voice, “Dancing ‘round the fact that you’ll be gone in a minute.” “Good Thing” is an intimate, ever-rising number that shimmers with orchestral energy as it details the “falling” part of falling in love. And on “Service Receipt,” deceptively upbeat banjos and guitars carry Pillsbury along, as does some of his most relatable lyrical work over a delicious, dancey drumbeat. “Trying to replace you / Falling pretty short / Leave the light on on my front porch / What’s one more night just south of you,” he sings scratchily as the song bursts open. Pillsbury is so convincingly sincere in his desire for a suspiciously Dakota Johnson-shaped beloved that, by the end of that mid-album run, the singletons among us are wont to be left with a slight back-of-the-throat nausea. Sincerity, after all, can be grating:  “Chuck’s Mantra,” the album’s a cappella opener, reeks of a guy who juuuuust started talk therapy. (And Pillsbury did; he keeps mentioning it in interviews.) Consider it a mercy, then, when Pillsbury offers up the caustic, solipsistic derogation that is “Stain.” It’s an unexpected song in the track order, arriving singularly mean and taunting. “It’s so vain / To be calling the house / It’s a stain / That I can’t get out,” he croons over a sneakily tropical, flute-driven instrumental. But a record like this one wouldn’t finish on such a heart-stabber. Enter “The Wedding”—soft guitars, symphonic pianos, and an idea centered around Timely entering his thirties and discovering that marriage doesn’t sound so bad after all—and “Harmony,” a tickly, stomp-clap piano ballad about things falling into place romantically for our young hero mechanic. And a hero he is: throughout the album, Pillsbury comes off, if nothing else, as not just exceedingly likable, but as the kind of person for whom we ought to root. If he wins, the listener does, too. It shouldn’t surprise anyone that Pillsbury’s Chuck Timely goes through a successful bildungsroman by the album’s end. A project like this isn’t meant to challenge the listener so much as pat them on the back for being attentive enough to follow the storyline toward its comforting conclusion. But Chuck Timely & the Hourglass does that duty with winking panache, enough to forgive its occasional descents into cliché and TikTok bait. It may not be entirely new, but the album is well-crafted, briefly compelling, and full of songs that could easily grab a spot on the pop charts. Go get ‘em, cowboy. [Interscope] Miranda Wollen is a staff writer at Paste and is based in New York City. Follow her @mirandakwollen or email her.