One of the biggest “what ifs” in country music.
Today is the 36th anniversary of the death of the legendary Keith Whitley, who’s still regarded as one of the greatest country singers of all time despite his career being cut all too short.
Whitley got his start in music as a member of Ralph Stanley’s band in his home state of Kentucky, alongside another bluegrass legend, Ricky Skaggs. And after making a name for himself as one of greatest bluegrass singers of the time, Keith moved to Nashville to pursue his country music career.
He dropped his first EP, A Hard Act To Follow, in 1984, but Whitley was still struggling to find his sound and the album was only a minor success. But he found it in 1985 with his debut full-length album L.A. to Miami, which featured classics like “Miami, My Amy,” “Nobody In His Right Mind Would’ve Left Her” and “Ten Feet Away.” And by the time he released his sophomore album, Don’t Close Your Eyes, it was clear that country music had something special with Keith Whitley.
When Keith Whitley sang, you felt every word of the pain in his music, of the emotion in his voice, and of his love for country music. But unfortunately, the pain in his music came from his own personal struggles, including his addiction to alcohol. And on May 9, 1989, Keith Whitley passed away at just 34 years old from an accidental overdose, putting an abrupt end to one of the most promising careers in country music.
I’ve said before that if Keith Whitley hadn’t passed away so young, he would be considered the King of Country Music over George Strait. What he accomplished over such a short career, and the legacy that he managed to leave behind, just prove how great he really was and make his loss all the more tragic.
And I’m far from the only one who feels that way. In fact, even Waylon Jennings agreed that Keith Whitley was maybe the greatest country music singer of all time.
Barry Walsh, who was Waylon’s former piano player, recalled being on his way home to Franklin, Tennessee on the day Whitley died. But knowing how much Waylon loved Whitley, he decided to go check on him.
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:
“He looked at me and he said, ‘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.”
High praise from a legend himself, but it just goes to show you what an impact Keith Whitley had on country music during his short time here on this earth.
And I still can’t help but think what could have been. It will forever be one of my big “what ifs” in country music.
Keith Whitley, man, what a legend.
