About the Song

Released in 1981 on their duet album Leather and Lace, “Wild Side of Life” brought together Waylon Jennings and Jessi Colter in a haunting reinterpretation of a country music staple—this time infused with the weary wisdom of two artists who had lived every word. Originally made famous by Hank Thompson in 1952, the song is reimagined here not as a one-sided lament, but as a duet filled with emotional complexity and lived-in sorrow.

When Waylon Jennings sings the opening verse, his voice is gravelly and low, weary but unwavering. There’s no anger in his tone—just the resignation of a man who’s watched the one he loves drift toward the neon lights. But when Jessi Colter enters with her response, the song changes shape. No longer just a tale of betrayal, it becomes a conversation—two voices circling each other, tangled in hurt, memory, and love that won’t quite let go.

Their real-life marriage adds a layer of authenticity that no studio pairing could manufacture. You can hear the understanding between them—not just as musicians, but as partners who had weathered storms both personal and public. In “Wild Side of Life,” they don’t just sing at each other; they know each other. That connection pulses beneath every line.

The arrangement on Leather and Lace is stripped back, traditional, and steeped in atmosphere. Steel guitar and piano echo softly in the background, giving space for the voices to breathe and the story to unfold. It’s pure country—unfiltered, unpolished, and deeply human.

While the original version of the song lamented a woman’s fall from grace, Waylon and Jessi turn it into something more nuanced—less judgment, more understanding. It’s about choices, consequences, and the parts of ourselves we sometimes can’t explain, even to the ones we love.

“Wild Side of Life” on Leather and Lace isn’t just a cover—it’s a reckoning. A slow, aching dance between two people who’ve seen both the wildness and the devotion up close. And in their voices, you can hear not just the pain—but the love that somehow, through it all, still remains.

Video

https://youtu.be/8VJzzg34gzA