“Hoss, That Was The Greatest Country Singer Ever” – Waylon Jennings On The Day Keith Whitley Died

Keith Whitley and Waylon Jennings country music
Michael Ochs Archives/Getty Images

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

35 years ago today, the great Keith Whitley passed away tragically at the very young age of 34 (possibly 33). After a long struggle with alcoholism, Keith ultimately succumbed to his addiction and passed from alcohol poisoning on May 9th, 1989.

Waylon Jennings would pass away almost 15 years later in 2002.

And though we unfortunately lost Keith (and both of them, rather) 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:

Keith Whitley’s Final Letter To Lorrie Morgan

Keith Whitley and Lorrie Morgan were a country music power couple in the late ’80s.

The two were married in 1986, until Keith’s tragic passing in 1989.

Though Lorrie was initially warned about Keith’s alcohol problems by his manager, Don Light, she hoped against her better judgement that her love for him would be enough to help him overcome his struggles:

“I thought as much as I loved Keith, surely that would help him. I feel in my own heart I kept Keith alive a lot longer because I was there all the time. I put everything on the back burner, including my career, to help Keith.

I never, never expected anything as bad as Keith had it. I thought it would just take love and someone to help him to get through with it. He wanted it that way. But something inside of him wouldn’t let him. It literally was like he had cancer and could not control.”

She always knew in the back of her mind that he was “a ticking time bomb”, and she lived in constant fear that something bad would happen to him:

“Every time the phone would ring it was in the back of my mind that there was somebody calling to tell me he’s been in a wreck or died of alcohol.

It was a living hell. I was on pins and needles when he was on the road. We had six great months of nothing but pure ecstasy. It was a heavenly marriage and home.”

On May 9th, 1989, the day he passed away, he had taken Lorrie to the airport to see her off on a promotional trip to Alaska. He gave her a hand-written letter before he left her there, which was not all that uncommon or out of character for him.

What he wrote to her, though, was almost like a farewell note.

When she read it again on the way home, in retrospect, she felt like he was trying to tell her something.

And it’s the most beautifully heartbreaking thing you might ever read:

“Would you like to know what I wish for you? If I could have any wish I wanted, this is my wish:

That in your life which is so precious to me, may worries, troubles and problems never linger. May they only make you that much stronger and able and wise. May you rise each day with sunlight in your heart, success in your path, answers to your prayers, and that smile that I always love to see in your eyes. I love you, Keith.”

And if you really wanna get in your feelings, check her out singing his stunning hit “Don’t Close Your Eyes” not too long after he passed away.

Written by Bob McDill, Keith released it as the third single from his album of the same name in 1988, and it peaked at #1 on the U.S. Billboard Hot Country Songs chart.

You can just hear the pain in her voice and she does such a beautiful job with this sweet tribute to her late husband, whom she lovingly calls “the best country singer that ever walked the face of this earth.”


The original:

A beer bottle on a dock



A beer bottle on a dock