Honoring Waylon Jennings On His Birthday With Some Of The Best Stories He Ever Told

Waylon Jennings country music
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Waylon Jennings is one of my favorite country artists of all time.

And in honor of today, what would’ve been his 86th birthday, let’s take a look back at some of the greatest comments he’s ever made, and greatest stories he ever told.

Y’all know that he received a motorcycle for his birthday one year and fired it up in his hotel room, but there’s plenty more where that came from. Waylon was never shy about sharing his life and his honest, raw thoughts about basically anything.

He did an interview with SPIN in 1988 that is pure gold, and full of honest little nuggets of wisdom that are as unique as he was. It’s a pretty lengthy read, so I pulled some of the best parts from it for your reading pleasure.

My biggest takeaway, honestly, is that Waylon is as real as they come. Plus, he’s freaking hilarious. A lot of us knew that already, and it’s part of what everyone loved so much about him.

Willie Nelson the “Outlaw”

He opened the interview exactly the way you’d think he would when the interviewer told him he would get in trouble if they published parts of the story:

“I don’t care. You write what I tell ya.”

When it came to the album he did with Willie Nelson, his wife Jessi Colter and Tompall Glaser called Wanted! The Outlaws, he’s not shy about admitting that framing the album that way was a big marketing tool and nothing more:

“No. No big story behind it. About the closest thing that Willie ever did to bein’ an outlaw is that he probably came to town and double-parked on Music Row.”

The interviewer proceeds to tell him he had a Willie Nelson for President bumper sticker and Waylon thinks it’s a horrible idea

“You do? Well burn that thing. If there’s anything you don’t want, Hoss, is Willie Nelson to be president. I mean, you don’t even want him to be Secretary of — you don’t even want him to be dogcatcher.”

And in one of my all-time favorite lines, he admits that the most “outlaw” thing Willie ever did was “double-park on Music Row.”

Then, he gets to a great tale about the time in the early days when he and Willie were big stars in Texas.  Willie picked him up in his new Mercedes from the airport and it broke down on the way to Willie’s house.

Willie Runs Out Of Gas

People would drive by and wave, but no one would stop and help:

“Well, when we were really hot in Texas. Willie picked up me and Jessi at the airport in his new Mercedes. This must be 12 or 15 years ago.

Willie runs out of gas. That’s just no problem, I mean, we’re in Texas, everybody knows us in Texas. Nobody would stop, I just couldn’t figure that out.

And finally, when the Lone Star Beer truck, which sponsored most of Willie’s shows, drove by, and the driver hollered, ‘Hey Willie, Waylon, what y’all doin,’ and kept goin’, well, I said, ‘Wait a minute now, Willie, I’m gettin’ tired of this.’ ‘We’ll set Jessi out here and get us a ride.’

I ain’t kiddin’, we was there over an hour and nobody would stop. They like us, they like our singin’, but they don’t want us ridin’ in their cars with em’ now.

They ain’t gonna give no hillbillies lookin’ like me and him a ride.”

And thinking about this in today’s context, I can’t imagine seeing Koe Wetzel or Parker McCollum and not stopping to help, ya know? What a reputation Waylon had.

And possibly the best one of all is when there was a booking mix-up between Waylon, Dotty West, Hank Snow and Conway Twitty.

Playing with Conway Twitty

Waylon said it was one of his favorite (true) stories from the road:

“We were booked one time up north here. This guy that booked us, and this was about 15 years ago, he sent me to Syracuse, where Dotty was supposed to be, and he sent me to Rhode Island, where I was supposed to be.

Well, we got up there in Syracuse, and I was there with Conway Twitty, and I have never seen that many ugly women congregatin’ in all my life, and I told him so.

I said ‘Boy, you do draw an ugly class of women.’

And he said, ‘Well, you were booked on the show, too.’ And I said, ‘Yeah, but I wasn’t advertised.'”

I mean, have you ever heard a funnier story in your life? What a gift he was. I don’t think something like that would pass in an interview today, but damn was he unfiltered and downright hysterical.

Not only do I think that wouldn’t pass, I can’t think of many artists today who would even say something like that in the first place.

Maybe that’s a good thing, I don’t know… but I miss when country music had characters like Waylon.

Oh, and another great moment came when he was asked what he thinks about award shows…

Honest About Awards Shows

Waylon was ahead of his time, saying:

“I think they’re a joke…”

He couldn’t be more right about that.

And, I’ll leave you with some sage advice Waylon had when it comes to what he wanted to be remembered for and how to find redemption in life:

“That you can, that a person can blow it… can make it and blow it and hit bottom doing drugs, and come back and be able to survive that and do something worthwhile.”

He was as real as they come.

Happy Birthday to the absolute legend of all legends, Waylon Jennings.

Check him out playing “Lonesome, On’Ry And Mean” at The Texas Opry in 1975. The man had more charisma and swagger in one finger than most people can even dream about:

And for one of my personal favorite songs, you need to see his 1984 performance of “Dreaming My Dreams” with you for his Live from Austin, TX album, where he said:

“I guess this is my favorite song I ever recorded.”

A beer bottle on a dock



A beer bottle on a dock