About the Song
A song for the soul’s quiet storms—when even the strongest men need a place to lean.
Released in 1974 on the landmark album The Ramblin’ Man, “Cloudy Days” is one of Waylon Jennings’ most tender and vulnerable recordings. Though widely known for his outlaw bravado and rough-edged style, this song offers a rare glimpse behind the legend—a moment of humility, honesty, and emotional clarity.
Written by Waylon’s longtime drummer and close friend Richie Albright, “Cloudy Days” is a tribute to Waylon’s mother, Lorene Jennings, who once told him during a hard season in his life:
“Don’t worry, son. Everybody has cloudy days.”
Those words became a lifeline—and eventually, a song. And when Waylon sings them, you feel it. You feel the weariness, the need for comfort, and the hard-won understanding that no man, no matter how strong, walks through life untouched by sorrow.
Musically, the track is stripped down and heartfelt. Waylon’s voice carries a weight that only life can teach—low, honest, and deeply human. There’s no rebellion here, no fight. Just surrender. Just a moment of asking the world, and maybe God, for a little light through the clouds.
In the context of the “Outlaw Country” movement that Waylon helped pioneer, “Cloudy Days” stands out as a deeply personal confession. It reminds listeners that even legends had mothers who loved them, words they held onto, and storms they had to weather.
For longtime fans, it’s a song of healing. For newcomers, it’s an invitation to see Waylon Jennings not just as a rebel, but as a man—one who could stare down the darkness, and still sing softly about the grace of cloudy days.
Because sometimes, the strongest thing a man can do… is admit that he’s hurting.