THE LEGEND
In the shadowy holler of Crooked Hollow, nestled deep in the Appalachian mountains, life has a way of shaping people into storytellers. It’s a place where the hills carry secrets and the rivers remember every heartbreak. It was there, surrounded by little more than hard work and hand-me-down dreams, that Waylon Crybaby and the Squeaky Wheels found their voices.The band’s story isn’t full of glamorous beginnings. It’s about grit, survival, and a love for music so strong that it pulled them through times that might have broken others.
Waylon Crybaby grew up the youngest of five kids in a one-room house that leaned hard to one side, “like it was tired of standing.” His daddy worked the coal mines, and his mama sang hymns to make the days feel shorter. Waylon always had a guitar in his hands, even when it was held together with binders twine. He earned the nickname “Crybaby” not because he cried often, but because his voice—raw and aching—sounded like a man bearing the weight of the world.
The Squeaky Wheels came together in pieces. Buckshot Billy, the guitar player, was Waylon’s childhood friend, known around town for his quick wit and even quicker fingers on the fretboard. Rusty Perkins, the pedal steel player, was a drifter who showed up in the holler one summer and stayed after playing a single tune at a backyard fish fry. Slim McCoy, the drummer, was the loud one, both in personality and percussion, and had spent years banging on everything from pots to bar tables before someone suggested he try an actual drum kit. Beau “Boomstick” Jenkins brought his upright bass into the mix, a steady presence in both sound and temperament. And finally, Daisy Mae Johnson, whose fiddle could break hearts as easily as it could light up a room, completed the group.The band started small: playing church socials, front porches, and the occasional honky-tonk that was willing to overlook their rough edges. Their early shows were unpredictable—sometimes magic, sometimes a mess—but there was something unmistakable about their sound. It was raw and honest, traditional country music with a hint of something deeper.
Word spread beyond the holler, and soon they were traveling farther, performing at small festivals and dive bars where the crowd always seemed to include someone who knew someone. Their big break came when they recorded their debut album, Coal Dust and Moonshine, in a makeshift studio built out of a converted chicken coop.
The album’s lead single, Rust, Dust, and Bad Decisions, struck a chord with listeners who recognized themselves in the band’s songs. Suddenly, Waylon Crybaby and the Squeaky Wheels weren’t just a local act—they were a rising name in country music. Fame wasn’t easy, though. The road wore them down, as it does for so many artists. Waylon struggled with the pressure of the spotlight, and his reclusive nature clashed with the demands of the industry. Rusty disappeared for a stretch, resurfacing months later with little explanation beyond, “I needed some air.” And Daisy Mae had to fend off critics who dismissed her fierce fiddling as “too bold” for traditional country, a claim she countered by playing even bolder.
Waylon Crybaby and the Squeaky Wheels aren’t chasing fame or fortune—they’re chasing the perfect song. And though they’ve come far from Crooked Hollow, their music still carries the echoes of the place they call home. Their story might not be flashy, but it’s real, and so are the songs that keep audiences coming back, wondering what parts of their story are true and which are just part of the mystique. The Squeaky Wheels will never tell.
