By the late 1970s, Waylon Jennings wasn’t just singing about being an outlaw.
He was living it.
After years of battling Nashville’s tightly controlled “Countrypolitan” system, Jennings — alongside Willie Nelson and others — helped ignite the outlaw country movement. The rebellion wasn’t just about sound. It was about freedom. Creative control. The right to record with his own band and shape his own identity without Music Row calling the shots.
Albums like Lonesome, On’ry and Mean and Dreaming My Dreams had already cemented his status. But by 1977, his personal life was unraveling under the weight of cocaine addiction.
In his 1996 autobiography Waylon, Jennings admitted just how dark things had become. He stayed awake for days at a time. He barely went home. His health declined. Cars were abandoned around town because he was too exhausted — or too wired — to drive them back.
Then came the federal drug bust.
While recording for Hank Williams Jr., Jennings received a package containing cocaine. His drummer, Richie Albright, famously flushed the drugs before agents could seize them. Jennings was arrested but never convicted. Still, the story made national headlines.
For most artists, that kind of scandal might have stalled a career.
For Waylon Jennings, it became fuel.
In 1978, he released I’ve Always Been Crazy on RCA Victor. The title track, written solely by Jennings, arrived as both confession and declaration. It shot to No. 1 on the country charts, holding the top spot for three weeks — proving that controversy hadn’t damaged his audience.
If anything, it strengthened the bond.
The song is brutally honest. Jennings doesn’t pretend to be innocent. He doesn’t deny his flaws. Instead, he leans into them:
“I can’t say I’m proud of all of the things that I’ve done,
But I can say I’ve never intentionally hurt anyone.”
That line captures the essence of Waylon’s outlaw persona. He wasn’t rebelling for image. He wasn’t crafting a brand. He was simply living loudly, imperfectly, and publicly.
The chorus flips the narrative entirely. Being “crazy,” he suggests, might actually be what keeps him sane in a world that tries to confine him.
The album also featured the pointed track “Don’t You Think This Outlaw Bit’s Done Got Out of Hand,” a self-aware nod to the commercialization of the very movement he helped create. By 1978, outlaw country had become mainstream — platinum records, arena tours, major-label backing. The rebellion had, in some ways, become the establishment.
But “I’ve Always Been Crazy” cuts through all of that.
It’s not polished. It’s not defensive. It’s defiant.
The song stands as a snapshot of a man at the edge — battling addiction, wrestling with fame, and refusing to apologize for who he was.
Waylon Jennings didn’t just sing about being an outlaw.
On that record, he proved he understood exactly what it cost.