On This Day 37 Years Ago, We Said a Premature Goodbye to the Rising Star Waylon Jennings Deemed “The Greatest Country Singer Ever”

Keith Whitley remains one of country music’s greatest “what-if” stories. Releasing just two albums in his short lifetime, Whitley helped lead the charge on the 1980s New Traditionalist revival of country music with No. 1 songs like “When You Say Nothing At All” and “I’m No Stranger to the Rain”. Sadly, the CMA Award-winning artist never could overcome his lifelong struggles with alcohol use. On this day (May 9) in 1989, Keith Whitley’s brother-in-law found him face-down and fully clothed on his bed at his Nashville-area home. Just 34 years old, he was later pronounced dead from acute alcohol poisoning.

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This Outlaw Legend Was “Gutted” by the Loss of Keith Whitley

According to Barry Wallace, Waylon Jennings’ former piano player, news of Whitley’s death “gutted” the “Luckenbach, Texas” crooner.

In fact, Wallace recalled Jennings looking at him and saying, “Hoss, that was the greatest country singer ever.”

Born July 1, 1954, in Ashland, Kentucky, Jackie Keith Whitley grew up 46 miles away in Sandy Hook. Music was always an integral part of his upbringing, and after he won a talent contest at age 6, his father, Elmer, bought Whitley his first guitar.

As a teen, Whitley formed his own band with older brother Dwight, a banjo player. He had a taste for danger even then, drinking bootleg bourbon and racing cars down mountain roads with his friends. But he remained devoted to his craft, absorbing both the bluegrass of his home state and traditional country artists like Lefty Frizzell, George Jones, Hank Williams, and Merle Haggard.

Whitley and Ricky Skaggs met at a talent show in Ezel, Kentucky. Instantly bonding over their love for bluegrass music, they formed a Stanley Brothers tribute band. So on point were their harmonies that they were mistaken for the real thing by Ralph Stanley himself, who hired them both as members of his band.

Pivot to Country Music

After achieving considerable success on the bluegrass scene, Keith Whitley moved to Nashville in 1983 to pursue his other passion: traditional country music.

[RELATED: Top 8 Traditional Country Songs of the ’80s]

Signing with RCA Records, his debut full-length album, L.A. to Miami (1985) spawned the Top 10 singles ““Ten Feet Away,” “Homecoming ’63,” and “Hard Livin’.”

However, Whitley truly found his groove on his sophomore effort, 1988’s Don’t Close Your Eyes. That brought three straight No. 1 hits: the title track, “When You Say Nothing at All”, and “I’m No Stranger to the Rain”.

After his death, Whitley’s mentor, Ralph Stanley, wrote in his 2009 memoir, “Nobody sounded like Keith. When you heard him on the radio, you knew who it was. If he had lived, he would have been one of the greatest singers Nashville ever saw. But he had something deep down inside of him that wouldn’t let him alone.”

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