Waylon Jennings Told Conway Twitty He’d “Never Seen That Many Ugly Women In My Life” Opening A Show For Him In The Early Days

Waylon Jennings country music
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I don’t think it’s any secret that Waylon Jennings was never afraid to say exactly what was on his mind.

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 totally changed the game by being exactly and authentically himself.

It’s hard to narrow down my favorite Waylon stories, but one that is certainly in my top five is a true one from the road during the early days of his career.

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.

READ NEXT: The Iconic Story Of George Jones Getting Drunk, Punching Waylon Jennings In The Face, And Waylon Tying Him Up

Moreover, 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… but I do miss when country music had characters like him.

He wasn’t kidding around when he wrote this one…

“I’ve Always Been Crazy”

How A DEA Raid Inspired “Don’t You Think This Outlaw Bit’s Done Got Out Of Hand”

Waylon Jennings is one of the greatest storytellers of all time.

And that’s due in large part to the fact that his songs told honest, authentic, and real life stories about his lived experiences and things that he went through… the good, the bad, and often… the ugly.

One of the more insane stories I’ve heard about him was the time that he got arrested for cocaine possession… or, lack thereof.

His son, Terry Jennings, gave more details about the story in his autobiography Waylon: Tales of My Outlaw Dad.

Waylon’s heavy drug use was never a secret, and he often talked about it later in his career once he got sober. For a long time, he took pills, but stopped after Elvis’ death in 1977 at the young age of 42. After that was when he started doing cocaine, often spending $1,500 a day on coke.

Eventually, DEA agents got on his trail after someone sent Waylon an ounce of cocaine as a gift through a private delivery service.

An employee (snitch) at the service was suspicious of what was in the package and opened it, discovering the cocaine that was inside. They then notified the Drug Enforcement Agency about the contents of the package, and the DEA took almost all of it.

But, they left a small amount in there and sent it on to Nashville, hoping they could bust Waylon. It was delivered to Waylon at the studio where he was recording.

In Terry’s book, he wrote:

“Dad took the package into the studio area, opened it, saw what was inside, and went back to work.

Next thing you know, DEA agents were coming through the doors and into the control room.”

Waylon’s drummer, Richie Albright, came into contact with them first, and he hit the call button so that Waylon could hear everything inside the recording room, where he could see out but the agents couldn’t see him.

Of course, Waylon jumped into action, tossing it away, where it slid behind some baseboard at the base off the wall and continuing to record the song and work as if nothing was going on. It sounds crazy, but the truth is often stranger than fiction, isn’t it?

The agents waited for him to come out, and eventually showed him they had a warrant. But, there was a problem with it… he was listed as the owner of the studio, except he wasn’t. He rented that studio, but did own his office that was right next door.

So of course, they had to leave and go get a correct warrant before any arrests could be made. During that time, Richie worked to flush the coke down the toilet.

He said everyone could hear the toilet flush, and when he walked out of the bathroom, a DEA agent was standing right there with his face bright red because he was so angry they no longer had any evidence or proof of them having cocaine.

Finally, one of the agents straight up asked Waylon where the cocaine was, to which Waylon replied,

“If it ever was here, it’s ain’t here no more.”

Waylon Jennings was stone cold.

Sometimes, I forget he was actually a real person because of his larger than life persona and ability to be true to himself 100% of the time, no matter what. The DEA guy sarcastically responded to him, “I’ll bet it ain’t”.

The kicker here, though, is that even though they got rid of all the evidence of cocaine, Waylon was still arrested on August 23rd, 1977 and charged with conspiracy and possession of cocaine with intent to distribute.

Before DEA took him away, he called his wife Jessi Colter and told her to get rid of anything and everything that could be used against him as evidence. She wrote about it in her book, An Outlaw And A Lady, remembering that he told her this:

I need you to go through all my things, I mean everything, and flush down the toilet anything that even looks suspicious. Do it now.”

He stayed away from the house until he could get things cleared up, but it terrified Jessi in the meantime as press reports got leaked all over the country about what went down.

After Waylon hired two “big-time lawyers” from New York City, all charges were dropped after a preliminary hearing due to the bad warrant, Terry says:

Behind the scenes, the prosecutor told Dad that because of the bad warrant, they had nothing on him.”

The whole ordeal inspired Waylon’s song “Don’t You Think This Outlaw Bit’s Done Got Out of Hand,” and it seems like this time in his life made it hard for Waylon to truly distinguish between the “outlaw” man he portrayed as part of his image, and the real man he was in everyday life.

The song was a solo write by Waylon, and was released in 1978 as the second single from his album I’ve Always Been Crazy, eventually peaking at #5 on the Billboard Hot Country Singles chart.

It took him six years after this incident to finally quit his drug addiction, but once he did, he stayed sober for the rest of his life.

You can watch Waylon explain a little bit of the story himself:

And of course, the country classic that’s based entirely on a true (and pretty badass) story:

SAD COUNTRY SONGS. Get the apparel from Whiskey Riff Shop.

A beer bottle on a dock



A beer bottle on a dock