He was a pioneer in the genre and never seemed to be afraid to speak his mind and say whatever he felt. He was driven by a single-minded purpose, to make country music, and if something got in the way of that, he’d figure out a way to get around it.
He was interviewed years ago on Nashville Public Television in promotion of his book which was released in 1996, Waylon: An Autobiography. They dove deep into some of the elements that made Jennings a country music icon, and he also tells a few stories that personify his infamous outlaw spirit.
John Seigenthaler, who conducted interview, pressed him on where he got his relentless drive and motivation from:
“Everything [my grandpa] did was against the grain. And I more or less did that, too.
But since the day I can remember the only thing, you know, I never liked to be told what to do. I just didn’t like to be told what to do. And I didn’t like for people to do things wrong.
But as far as the drive I had for that, it was just something that was born in me and it’s still there. They called it outlaw, they called it all kinds of things, and all it was, was I tried to do right by people. I was taught that.”
They go on to talk about a story in the book where Waylon tagged along to the studio for a meeting with executives at the label regarding Willie Nelson’s now-iconic 1975 album, Red Headed Stranger.
Waylon Saves The Album
Waylon and Willie shared a manager, Neil Reshen, and he was the one who’d invited Waylon to come listen in on the conversation.
Apparently, the executives decided they wanted to bring in the famous producer, Billy Sherrill, to help ‘fix’ the sound of the album… or they were going to toss it out all together.
That’s when Waylon chimed in on behalf of Willie in the most badass way possible:
“I like strings, and Billy Sherrill is great at what he does, but you don’t get me at all.
I said, ‘take that tape off or you won’t be my manager or Willie’s, either.’ I said ‘that’s stupid,’ you know, and I called him a bad name. And uh, he had not a clue about this music, and I said get it off.
So I got up and I said ‘I know I’m in your office, and I’m getting out. That’s it.'”
And luckily, Neil wanted to know why and told Waylon to sit down and explain what he was missing with the music:
“I told him, I said, all of it. You’re missing the whole thing. You’re missing what 70,000 people came to Dripping Springs [Texas] to hear.”
Neil listened again and decided to release it, though he made it clear to Waylon he still thought he was dead wrong.
“It wasn’t but about six months later I was coming down the stairs of my office, and I heard somebody say ‘There’s someone here to see you.’ And I said ‘Who is it?’ And he said ‘it’s that stupid…’ and repeated what I said, you know. And he brought me a gold album.
It was that ‘Red Headed Stranger’ album.”
I mean, thank goodness for people like him who would stand up for good music and knew when something had a purpose and needed to be heard. Can you imagine if that record had never been released?
Waylon had his finger on the pulse and understood what people wanted to listen to and what resonated with them.
In my opinion, what he says next is one of the main reasons he became so influential and important to country music.
He’s an icon because he always stood up for what he believed in and never groveled to the powers that be… because as this story clearly points out, they often have no clue what they’re even talking about:
“My problem is keeping my mouth shut. Sometimes it’s not even any of my business, but I can’t help it.
When I think something, like I knew that album was right, and I couldn’t just see it die like that. And it would have. It would’ve never happened.”