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Genre:

Pop/R&B

Label:

Interscope

Tucker Pillsbury says he’s playing a character called Chuck Timely on his new album, and it’s not the first time he’s had an alter ego. To promote 2024’s Kansas Anymore, the singer usually known as Role Model maintained a second social media presence, a crass imposter named Saint Laurent Cowboy who described his record as “a dude who just blew your fucking back out” and said things like “if you see a guy wearing a wool sweater on this app singing Gracie Abrams, just know he’s manipulating you, and he’ll probably give you some sort of a UTI.” This caricature of a TikTok douchebag seemed to come easy to Pillsbury, whose profile has risen over the past couple of years through a combination of inoffensive music and chronically online energy that splits the difference between bravado and nonchalance. With arms covered in patchwork tattoos and a choppy haircut that would look ridiculous on someone even five percent less handsome, Pillsbury is a perfect modern softboy, as comfortable perching on the couch of the excitable podcast host Jake Shane as he is gently swiveling his hips onstage.

His breakout moment last year was “Sally, When the Wine Runs Out,” a mild hoedown about falling in love with a drunk girl at a dive bar that got its viral juice from celebrity cameos at live shows. That pushed Role Model into the “Wait, Who’s That White Boy?” Class of 2025 alongside Alex Warren and Sombr, and it validated his turn from lo-fi hip-hop and e-boy bedroom pop toward the crunchier realms of folk and country. Now with his third studio album, he’s channeling a fictional time-traveling session musician he described as “pathetic in a charming way.” On the moodboard: names like Bruce Hornsby and Don Henley, album-oriented artists that mark a considerable change from earlier influences like Mac Miller and Kacey Musgraves.

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Pillsbury tapped two session musicians to lead production on Chuck Timely & The Hourglass: guitarist Mason Stoops and keyboard player Taylor Mackall, both longtime collaborators of the indie-folk artist Lizzy McAlpine (who appeared on the last Role Model record). The sound brings to mind an antique honky tonk full of patrons with prominent belt buckles and a jukebox that doesn’t play anything recorded after 1990—or, more accurately, the kind of place that opened three months ago but aims to look like that. Amid boot-scooting rhythms and saloon piano, Pillsbury sounds relaxed and pleasant, playing the part of a hapless but hopeful barfly who is happy to dust himself off and try again after a series of romantic entanglements that all end a little too soon.

His dalliances are often fueled by alcohol and tend to slip through his fingers. On the clearest Hornsby nod, “Song Is All You Get,” he gets misty about a gal who makes a big impression at a bar then skedaddles; on “Love I You,” which sounds, not unpleasantly, like a Jason Mraz deep cut from 2002, he begs his lover (played on a cutesy spoken bridge by his current girlfriend, Dakota Johnson) to stick around for last call; on the dreamy “Chasing Midnight,” he gets an invite to grab a glass with an old one-night stand who probably will make herself scarce soon: “Won’t be the first but it might be the last/I’ve been trying to make peace with that.” The great success of “Sally” has perhaps trapped Pillsbury in a dive bar of the mind—having connected to a wider audience through a story-song about a boozy hookup, he’s committed to pounding his beers and wiping his tears, running through fickle divas like it’s his job.

Sometimes it feels like the “rock journeyman with bandanna in back pocket” thing that Pillsbury is trying to do requires a little more grit than he can muster. He lays on the charm on lead single “High Hopes 3000,” a rollicking country singalong about optimistically hitting the town, but similar track ”Joy” is missing the kind of exuberant je ne sais quoi that made the classic rock he’s pantomiming classic to begin with. How is it possible to sound like you’re still playing it safe on a song with talkbox on it? Come on, Tucker! Songs like “Honeydew” and “Stain” start to drag the album down—the former is a stodgy piano ballad, the latter has an intriguing Margaritaville quality that doesn’t match the aimless lyrics. “Service Receipt,” on the other hand, is perfect, with Pillsbury mumbling sheepishly about being a “desperate motherfucker,” making corny puns about his romantic foibles (“Hell, I bought somebody flowers for a tulip kiss”—nice one), and even letting his usual laid-back vocals rip a little bit on the last chorus.

Pillsbury’s songwriting has come a long way in a short period of time—compare the “Nice Gal Works the Pole” clichés of 2022’s “stripclub music” to the thoughtful scene-setting of “The Wedding,” which has him fantasizing about committing to someone for life at a black-tie affair. And even though the roadhouse schtick feels cartoonish at times, he sounds like he’s having fun, which means Chuck Timely is pretty fun to listen to. Did he need to cloak these amiable tunes in the time-traveling alter ego? He seems to be using that character as a way to explain the multiple genre influences on the album (as well as its vague theme of “time”) but plenty of artists tap into sounds from multiple eras without needing to invent a whole new guy to justify them. Firing up a big neon sign that says “THIS ALBUM IS A RETRO THROWBACK” smacks of self-consciousness, and Pillsbury, who calls potential love interests “honey” as smoothly as a veteran diner waitress, who hypes up his backing band with frequent happy “woo!”s in the studio, doesn’t seem like a self-conscious man. “This is my comearound/Letting these walls come down,” he sings on the pretty closing track, “Harmony.” Maybe next time, Role Model won’t feel like he needs to play a role at all.

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