Waylon Jennings Said Keith Whitley Was “The Greatest Country Singer Ever,” Was “Gutted” On The Day Keith Passed Away

Keith Whitley Waylon Jennings country music

Waylon Jennings and Keith Whitley… two of the greatest to ever do it.

The late, great Keith Whitley passed away tragically in 1989, at the very young age of 34 from alcohol poisoning after a long struggle with addiction, and Waylon almost 15 years later in 2002.

And though we unfortunately lost Keith, and both of them, really, way too soon, his lasting impact on the country music community is one that is still felt to this day.

While his career was tragically cut short after just two albums (three more were released posthumously including Sad Songs & Waltzes), some would go as far to call Keith the greatest to ever do it. Some say he would’ve taken the “King” title from George Strait had he made more albums.

And “some” would include… Waylon Jennings.

Barry Walsh, Waylon’s former piano player, sat down with Otis Gibbs and told some cool stories about his touring days with Waylon. Apparently, Waylon was a big card player, and was always gracious with signing autographs and talking to fans (unless he was eating).

He would always make it known to his employees and band members that the autographs and extra stuff weren’t actually part of his job description, though, and he was really only there to get on stage and play the show. Classic Waylon.

Anyways, Barry has lots of fond memories of being in Waylon’s band, but a couple of them stick out more than the others. One of which was the time he went to Waylon’s house to tell him he was leaving the band, and he said he was shaking in his boots (literally) on the way there.

Even though they had a great relationship, Barry was terrified to disappoint his boss, but Waylon took it well and told him he was doing the right thing.

And the other thing he remembers very clearly happened a few years after Barry had left the band, and it was the day Keith Whitley died.

The Day Keith Whitley Died

Barry was on his way to his own house in Franklin, Tennessee, when he decided to stop by Waylon’s to check on him, knowing how much he loved Keith.

Waylon’s wife, Jessi Colter, answered the door and sent him to the den. Barry and Waylon sat down on the couch and watched the local news about Keith together for an hour or two just taking it all in.

At one point, Barry remembers Waylon Jennings looking at him and saying:

“Hoss, that was the greatest country singer ever.”

Needless to say, he took it pretty hard:

“He was gutted, he was really, really upset about that… as a lot of us were.”

To hear such high praise from an icon like Waylon Jennings (someone who’s arguably worthy of the title himself) is a serious deal.

I mean, if Waylon says you’re the greatest, then you’re the greatest, right?

I suppose we can save that debate for another time…

Check it out:

A beer bottle on a dock



A beer bottle on a dock