Willi Carlisle has always been one for grand lyrical gestures. Over his nine-year recording career, the folk singer-songwriter has addressed the Big Things in life—love, loss, sexuality, labor—with one-liners that would feel as at home in an inspirational quote calendar as his quirky, open-hearted compositions. “The heart’s a big tent / You gotta let everybody in!” goes the full-blooded refrain of the opening track of his breakthrough album, 2022’s Peculiar, Missouri. That’s arguably the definitive line of Carlisle’s discography (he even alludes to it in his Instagram bio), as his songs are warm embraces from a pair of arms with whose wingspan knows no limits. If you identify with a chronically misunderstood magician, two-headed lamb, or any outcast who, as Carlisle meditates on the title track of his aforementioned sophomore album, “may be too much for this world,” there is room for you in his generous, lived-in gospel.
Over the three years since Peculiar, Missouri, Carlisle has remained dedicated to practicing such unconditional empathy in his music. In fact, he’s only grown more ferocious in articulating his mission statement, stripping it of unpretentious metaphorical drapery and whittling it down to its most pointed form on the title track of his newest album, Winged Victory: “I believe in the impossible / That no one is expendable!” Isolated, the beamingly idealistic couplet might warrant an eye-roll, but Carlisle doesn’t treat it as the fluffy stock phrase lesser songwriters might. In the song, it sounds like a genuine lightbulb moment, sparked by a distinctly Carliselian plot development.
Traversing the open roads one night, chewing on meaty concepts such as love’s ephemerality, the mystery of songcraft, and the false promise of linear social progress, the troubadour narrator stops in Arkansas—Carlisle’s longtime home base—where he encounters a donkey named Winged Victory. The dissonance between the animal’s ungainliness and grandiose, aerial-coded moniker is undeniably comic and rich with symbolic potential. Carlisle’s recollection of the creature certainly sells that possibility: His cartoonish, chest-on-fire bellow conveys the sense of wonder generally reserved for sightings of equines who have literally sprouted cherubic wings from their bristly backs. Without saying so explicitly, he urges: Come! Look! The unlikeliest things, he emphasizes, can catalyze profound revelations.
That donkey is an evocative-enough figure to inspire the title of Carlisle’s fourth studio album, his first self-produced effort, and appear (sans wings) in the center frame of its intricate cover design. But there’s much more to see throughout the tracklist: a worm spits gold, divine intervention occurs in a public restroom, sugar is pumped “from the udders of the angels.” There’s also a polka instrumental interlude, and the woefully underutilized root word “lollygag” surfaces twice. In one of several playfully erudite, self-written reflections included in press materials accompanying the album, Carlisle brands himself a believer in nonsense, and, indeed, there’s a lot of that over the record’s 35-minute runtime.
Importantly, “nonsense” is not synonymous with vacuity. The absurdities of Winged Victory seem to rub off their magic onto the minor miracles of everyday life, prompting us to see things we’d ordinarily glance over—forget-me-nots flowering in a parking lot, berries bursting at the bottom of the waffle served at a shitty bed-and-breakfast, a peace sign graffitied in a dingy alleyway—under heavenly lighting. While generally focusing on the collective, Carlisle zooms in on little things and lives across Winged Victory, swirling the surreal and the banal into compelling images that compose a loose narrative provoking reflection on what it means and takes to be “free” in a nation with one foot shuffling farther back into the muck of the past more hastily than it may care to admit. Wisely, he doesn’t attempt to offer simple answers to these lofty questions, allowing for a necessarily nuanced composite. But if he offers any crucial takeaway, it’s that amid the daily slog of mind-numbing TV shows and frozen dinners, there is something triumphant about consciously celebrating and remembering the good.
The album’s lead single and centerpiece, “Work is Work,” best spotlights Carlisle’s aptitude for crafting keep-your-head-up anthems that are rousing, rather than patronizing, sunshiney fodder. He surveys capitalism’s exploitation of the working class and environment with an unflinching eye, sketching a “dope sick” sun looming over a town slumped towards the sea that heralds another hard day’s work for the locals while “all the rich folks come vacationing.” Instead of inciting a rabble-rousing revolution in response to this injustice, the chorus offers a simple proposition: That we remember the value of our labor and love despite despair. It isn’t a cure-all solution, but it is a step we can all realistically take to make the most we can of a system as deeply flawed as it is ingrained. The hope it inspires is sustainable, like a meal that isn’t as fantasy-inspiring as a sumptuous dessert, but is affordable and energy-sustaining. The bluegrass musical arrangement beautifully parallels Carlisle’s forward-facing message in its frisky, rough-and-tumble romp towards an everybody-sing-along finale, while fiddler Beth Crisman and singer-songwriter Brennen Leigh’s bright harmonies capture the community spirit at the heart of the song: the joy that crackles in the choir of their voices like sparks flying from a hearth makes you itch to join in.
Like Carlisle’s esteemed live performances, Winged Victory plays through like a vaudeville show, situating itself in an acapella hymnal, invigorated covers of dusted-over folk standards, and a neighborhood of raunchy musical comedies. Each act positions Carlisle’s voice as the center of gravity, showcasing his versatile showmanship—his presence is as magnetic when he belts against blindingly fast-paced latticeworks of banjo and blaring horns as when he whispers in a heart-in-throat warble over strings that drift in like the semi-lucid closing credits of a dream. Flashes of his trademark sense of humor—which almost always serves as an effective gateway into potentially difficult conversations—are particularly welcome, considering the heavy-heartedness of his last album, 2024’s Critterland. (The funniest bit on there was about a friend’s suicide letter being too wordy for cops to parse.)
Unfortunately, the expense of Carlisle’s indulgence in his extensive musical interests is a composite that lacks cohesion. I wonder if it may have benefited from some conceptual framework—perhaps interstitial spoken-word interludes to simulate a live experience—as occasionally stilted sequencing disservices some songs. The philosophical, finger-picked lullaby “The Cottonwood Tree” is as fragile and pretty as a porcelain figurine from childhood, but it lacks the bubble wrap it warrants, shoved between two theatrical, in-your-face numbers. And while the talking-blues tale “Big Butt Billy”—a trucker narrator’s account of falling for a blue-haired, septum-pierced, “callipygian,” non-binary server—will surely be a hoot live, in the context of the album as a whole, its loquaciousness renders it a jarring detour from the gorgeous rendition of English folk singer-songwriter Richard Thompson’s “Beeswing,” a wistful, Gaelic-tinged ballad that waltzes into focus like a far-away memory resurfacing. While Willi Carlisle embodies a misty-eyed grandfather recounting the one that got away on the latter, he starts to sound like an endearing yet socially unaware barfly who traps you in unilateral conversation on the former. (I’m no prude, but I hope to never hear an ass referred to as a “doo-doo house” out in the wild.)
Winged Victory’s clunkiness isn’t egregious, but it’s relatively stark in the shadow of Critterland, whose fully realized vision assured its marrow-deep resonance. Those songs—memoirs set to equally intimate Americana arrangements—register as a series of heart-punches, with the cumulative effect of their succession leaving the powerful impression that you have to hurt to achieve catharsis. Carlisle’s latest release may not be his magnum opus but, still, it’s a substantial entry into the contemporary canon of American folk music. As the ongoing ascent of country music is arguably intertwined with that of conservatism, Carlisle feels like a breath of fresh air for his fashioning of trad-folk arrangements as mediums through which to advocate for the queer community, people of color, and other marginalized groups.
His selected covers on Winged Victory, however—in addition to “Beeswing,” a century-plus-old laborers’-rights anthem (“We Have Fed You All for 1000 Years,” popularized by Utah Phillips on his 1983 album of the same name), a meditation on internalized homophobia (the Patrick Haggerty-fronted, queer country band Lavender County’s hilarious staple “Cryin’ These Cocksucking Tears,” to which Carlisle lends great nuance with a heart-warming new verse), and a tribute to the late, trailblazing Black cowboy and rodeo star Bill Pickett (“Old Bill Pickett,” written by the folk singer Mark Ross and based off of the cowboy poet Zach Miller’s epitaph)—subtly yet strikingly remind that many of the most enduring folk songs have been boundary-pushers, those to counter the ubiquitous “good-old-days” bullshit by honoring the gritty realities and improbable accomplishments of undersung, working-class heroes.
The covers’ evergreen relevancies (underscored by Carlisle’s lively performances and the fact that he sings about the issues they address on his self-written tracks) also raise the question: How much can a song accomplish as a political force? As time passes, it feels increasingly naïve to propose that a song can radically change the world, simple as that! Willi Carlisle doesn’t seem so wide-eyed as to suggest that—he’s certainly a dreamer, but he’s sporting some eye bags, too. Still, it’s difficult not to envision his gaze glimmering when he recalls what might be the most moving event to transpire on Winged Victory: “I sang to the dementia ward, and the bastards all sang back!” he proclaims in a thunderous, awe-inspired baritone. He understands that to keep singing while it all falls apart is no easy feat.
Anna Pichler has written for Paste since 2024, and she interned for the music section in the spring of 2025. When she’s not writing about music, she’s working towards an undergraduate degree in English literature at The Ohio State University. Keep up with her work on X @_Anna_pichler_ and Bluesky @annapichler.bsky.social.
