By 1999, country music had changed dramatically from the industry Waylon Jennings entered in the late 1950s and early ’60s. Glossy production, arena tours, polished marketing campaigns — the landscape looked very different from the gritty, rebellious days that helped spark the outlaw movement.
And yet, when Jennings appeared on PrimeTime Country in 1999, he didn’t sound bitter. He sounded amused.
Sitting comfortably as a legend rather than a chart-chaser, Waylon offered a perspective that was equal parts sharp, funny, and deeply sincere. He had already spent decades pushing back against Nashville’s expectations. Alongside friends like Willie Nelson and Kris Kristofferson, he had built the outlaw movement on one simple principle: artistic freedom.
So when he looked at the state of country music in 1999, he did so with the calm of someone who had nothing left to prove.
During a fan Q&A, Jennings surprised some viewers by praising several contemporary artists. He name-dropped Andy Griggs, Leroy Parnell, and Travis Tritt, suggesting they had staying power. But it was the women of country who impressed him most. Speaking of Trisha Yearwood, he said, “She just kills me. She’s a great singer.”
It was classic Waylon — honest, generous, and direct.
Still, he admitted that parts of the industry felt foreign to him. Image consultants. Branding strategies. Carefully crafted personas. With a grin, he asked the crowd, “Can you imagine me and Willie Nelson in a room with image consultants?” Then came the punchline: “He’d come out without one. I’ve blown every image I ever had.”
The audience laughed — because it was true.
Waylon had never been interested in polish. His entire career had been built on resisting the idea that record labels should dictate sound or style. He even recalled being asked to write songs “that the record company wanted.” His response was pure outlaw: “Who cares about what the record company wants? They’re supposed to sell what you do.”
By 1999, Jennings wasn’t an outsider because he failed to adapt. He was an outsider because he refused to compromise. And in that refusal, he remained exactly who he had always been.
There was no bitterness in his words — just a seasoned artist looking at a changing industry with a mixture of humor and conviction. If country music had grown slicker, Waylon remained rough around the edges. If marketing had grown louder, he stayed grounded in songwriting.
Two decades after helping reshape country music, Waylon Jennings proved that the outlaw spirit wasn’t just a phase of the 1970s.
It was a way of life.
And in 1999, he was still living it — laughing all the way.