Always Been Crazy – Waylon Jennings (Live)

Unknown session from August 7, 1984.

“I’ve Always Been Crazy” by Waylon Jennings is a bold, introspective anthem of defiance, self-awareness, and unapologetic individuality. Released in 1978, the song topped the Billboard Hot Country Singles chart and became one of Jennings’ most iconic outlaw country hits. It speaks directly to the tension between personal freedom and societal expectations, with Jennings embracing his outsider status in both the music industry and life.

The lyrics revolve around the narrator acknowledging his unconventional behavior—being “crazy”—but not as a flaw to be fixed. Instead, it’s something he accepts and even celebrates. Jennings sings about the cost of living life on his own terms, suggesting that his “crazy” ways may have cost him things like stable relationships or the approval of others. But he makes it clear that he wouldn’t change a thing. This attitude reflects the core of the outlaw country movement he helped lead, rebelling against the polished Nashville sound and favoring raw honesty.

Musically, the track rides on a mid-tempo groove with a blend of rock-influenced guitar licks and traditional country instrumentation, matching the gritty yet heartfelt tone of the lyrics. Jennings’ deep, distinctive voice delivers every line with conviction, reinforcing the idea that this isn’t just a song—it’s a statement of personal truth.

Underneath the swagger is also a glimpse of vulnerability. Jennings hints that the line between madness and authenticity is thin, but he’s willing to walk it. Lines like “I’ve always been different with one foot over the line” show a man aware of his contradictions, yet at peace with them. It’s a declaration of self that resonated with many who felt out of step with the world around them.

Ultimately, “I’ve Always Been Crazy” is more than just a country hit. It’s a manifesto for the misfits, a reflection of Waylon Jennings’ uncompromising life, and a reminder that being true to oneself—even at a cost—is its own kind of freedom.