Waylon Jennings Once Told Conway Twitty “I’ve Never Seen That Many Ugly Women In My Life” Opening A Show For Him

Waylon Jennings country music
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The one and only Waylon Jennings would’ve been 85 years old today.

Born on June 15th, 1937, in Littlefield, Texas, he dropped out of high school at age 16, determined to become a full-time musician.

In 1958, Buddy Holly arranged Waylon’s first recording session, and hired him to play bass. In 1959, while on tour with Buddy and his band, Waylon famously gave up his seat on the plane that crashed and ultimately killed Buddy, J. P. “The Big Bopper” Richardson and Ritchie Valens.

He eventually became a pioneer in the country outlaw movement of the 1970’s, but admitted plenty of times that was more of a marketing strategy than anything else, and once said that the most “outlaw” thing Willie ever did was “that he probably came to town and double-parked on Music Row.”

He was chock-full of great stories and authentic commentary, and was never one to shy away from saying exactly what was on his mind.

And in honor of his birthday today, I want to look back at one of his favorite (true) stories from the road.

In a 1988 interview with SPIN, Waylon talked about the time that a promoter booked him for a show with Conway Twitty, though his name wasn’t out there in all the advertising ahead of time due to confusion with the different shows up north they were appearing at with Dotty West:

“Well, now my mind is goin’ a hundred miles an hour. You know, dain bramage has set in. Probably the best story I got, maybe not the best one, but it’s true.

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.”

When Waylon got to Syracuse for one of the shows, he took a very unpolitically-correct approach, saying that he’d never seen so many ugly women in one room in his life.

And of course it was all in jest, but it being Waylon, he couldn’t let Conway (who was known for driving the women wild) get off without some friendly shit-talking:

“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.’”

Conway reminded him that it was both of their shows, to which perfectly replied with this:

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

I about spit my coffee out when I first read that.

Waylon was certainly one of a kind, but I don’t think something like that would pass in an interview today. 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.

And maybe that’s a good thing, I don’t know… I kind of miss when country music had characters like him.

So here’s to the late, great Waylon Jennings… he wasn’t kidding around when he wrote this one:

“I’ve Always Been Crazy”

Waylon Jennings Used To Brag About How He Didn’t Drink

Waylon really was one of a kind.

A cornerstone of the outlaw country movement, Waylon Jennings, can tell a story as well as anybody. Especially, from his time on the road and his wild days starting out in country music.

From riding Buddy Holly’s motorcycle around in his hotel room, to flushing a ton of cocaine down the toilet during a DEA raid at the studio, he’s seen (and done) it all.

For better of for worse, he truly lived the outlaw life he wrote about in his songs, and that authenticity is what we all loved so much about him.

And I’m sure if he was around today, he’d tell you there is nothing glamourous about being a drug addict, but nevertheless, the man was always extremely candid in interviews about all the shenanigans that went on during his hey day. The good, the bad, and the ugly…

And back in 1988, in an interview with SPIN, he admitted that he actually never drank all that much like one might assume, and he always wore that as a badge of honor, bragging to people about how sober he was.

The only thing was, he had quite bad drug problem for many decades (which he was very public about later on), and at the peak of his using, would often spend $1,500 a day on cocaine:

“I never did drink. That used to be one of my big brags. I would sit around and say, ‘I don’t drink and I never did drink.’

There I’d be just stoned out of my gourd on cocaine, but I was real proud of myself because I never did drink.”

Classic Hoss…

You could always count on him to tell it exactly how it was, and I think his self-awareness and willingness to poke fun at his own imperfections and flaws is actually quite endearing.

Waylon did eventually kick his drug habit when he got a little bit older, thanks in large part to help from his wife Jessi Colter and his son Shooter, but when people would recall stories of drinking with Waylon out on the road (which never actually happened), he’d just smile and nod:

“I’ve had times when people would come up to me and say, ‘Hey, remember when me and you used to get drunk back in Phoenix there?’

And I learned a good lesson: the best thing to say is ‘Yeah, we had a good time, didn’t we?’ Although it never really happened because I never was a drinker.”

There were plenty of times that the outlaw bit did get out of hand, but lucky for us, the country icon lived to tell all the crazy, and almost unbelievable, tales.

However for Waylon, as much as he talks openly about the wild days, it was the redemption that he wanted to be remembered for. A living reminder that anybody can come back from rock bottom:

“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.” 

Cue up the “Don’t You Think This Outlaw Bit’s Done Got out of Hand”:

Johnny Cash & Waylon Jennings Talk Drug Abuse In 1985

Always keeping it real.

Way back in 1985, both Waylon Jennings and Johnny Cash stopped by Late Night With David Letterman, and while the conversation started out pretty jovial at first, it quickly turned into a heavy one.

Letterman recalls that the last time Waylon was on his show, Johnny was sick.

Johnny, with a bit of a smirk, asked:

“Under the weather? Was that when I was in alcohol and drug treatment center?” 

To which Waylon replied:

“No, you were in the hospital. I was still on drugs, you were off of ’em at this point.”

And with a certain element of humor, they both went on to detail more about their struggle with drugs, their reasons for taking drugs, finally getting off them, and then Waylon, who was 11 months sober at this point, said that he used to spend over $1,000 a day on drugs. $1,000 PER DAY.

“You can’t believe what that can do for your taxes too.”

Pretty wild, eh?

And yet, nearly 40 years later and they’re still two of the realest artists to ever play the game.

And for more from Waylon and Johnny, check out this compilation video featuring various late night interviews from the ’80s and ’90s.

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