About the Song
Released in 1972 as part of Waylon Jennings’ Good Hearted Woman album, “To Beat the Devil” showcases Jennings’ thoughtful side through a powerful, contemplative cover of Kris Kristofferson’s seminal composition. This track stands out not for bombast but for its emotional weight, its quiet drama, and its honest grappling with life, temptation, and purpose.
From the opening lines, the song situates us in a world of struggle and aspiration. Jennings sings, in effect, of a musician’s life: the cold nights, the meager pay, the hunger for meaning, and the temptation to surrender to darkness. The “devil” in the title is both literal and symbolic—it evokes inner battles, external pressures, and the cost of holding on to integrity. And through his delivery, Jennings inhabits that tension with lived wisdom, as if he has wrestled with those forces himself.
Musically, the arrangement is straightforward yet effective. It allows Jennings’ voice to occupy the space fully—raw enough to feel his scars, but measured enough to convey purpose. The backing instrumentation supports without overwhelming, giving room for each lyric to land with clarity. His approach is not to re-invent but to re-interpret; he honors Kristofferson’s original message while making it speak in his own tone.
What makes “To Beat the Devil” compelling—especially for mature listeners—is its layered perspective. It’s not a song of bragging over having won every battle. Rather, it’s a confession, even a hopeful plea: even amid doubt and darkness, the fight is ongoing. Jennings offers no comfortable illusions; instead, he offers companionship in the struggle. For those who have known sacrifice, heartbreak, and the lure of easy escapes, the song is a reminder that meaning is often carved by persistence.
Within Jennings’ body of work, this cover holds a special place. It connects him to the poetic, philosophical edge of country music that Kristofferson embodied, while reaffirming Jennings’ own voice—one forged in hardship and honesty. “To Beat the Devil” is not just a song to listen to; it’s a song to sit with, feel, and reckon with—long after the last note fades.