Waylon Jennings Once Said There Were More “Ugly Women” At A Conway Twitty Show Than Anything He’d Ever Seen

Conway Twitty

Of all the absolutely fantastic stories I’ve heard about Waylon Jennings over the years, this is easily one of my favorites.

And I certainly don’t think it’s any secret that he was never afraid to say exactly what was on his mind, and if this isn’t proof, I don’t know what else could be.

Born on June 15th, 1937, in Littlefield, Texas, Waylon 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 because of it.

And in a great 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 her 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 mean, who else could put it quite like that and get away with it… hilarious. What a legend. Waylon was certainly one of a kind, but I don’t think something like that would pass in an interview today.

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”


A beer bottle on a dock



A beer bottle on a dock