About the Song
Long before he was crowned one of the leaders of the outlaw country movement, Waylon Jennings was a young artist finding his voice in a Nashville system not yet ready for what he had to say. One of his earliest breakthroughs came with the quietly powerful “That’s the Chance I’ll Have to Take,” released in 1965 as part of his early catalog on RCA Victor. Though it didn’t shoot to the top of the charts, the song became a crucial step in establishing the raw honesty and quiet defiance that would soon define Waylon’s legacy.
At its core, “That’s the Chance I’ll Have to Take” is a song about risk — emotional, personal, and romantic. Waylon sings of a man torn between the safety of what’s known and the vulnerability of chasing a love that may not last. “Troubles, I’ve found, are a part of the game, / And I’ve got to pay for my mistakes,” he sings, not with regret, but with acceptance. The lyrics capture the essence of a man willing to own the consequences of his choices — a theme that would echo through the rest of Waylon’s career.
Musically, the track is rooted in traditional country, with a soft shuffle rhythm, steel guitar, and a smooth vocal that hints at Waylon’s future strength. His voice here is gentler than in his later outlaw years — tinged with youth and vulnerability — but even in its restraint, you can hear the restlessness beneath the surface. He wasn’t just singing a song; he was beginning to shape a sound and philosophy that would eventually challenge the very rules of the Nashville establishment.
What makes “That’s the Chance I’ll Have to Take” resonate so deeply is its universality. Everyone, at some point, has faced a moment where the heart urges a leap, even when the head warns otherwise. Waylon doesn’t promise that love will work out — only that it’s worth the risk. That simple, stoic honesty is what makes the song quietly profound.
Looking back, it’s easy to hear in this track the early embers of rebellion — a man stepping onto a path that would lead him far from country music’s polite center and toward something wilder, freer, and more true. And for Waylon Jennings, taking the chance was never just a lyric. It was a way of life.