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HE ONLY LIKED TWO BOB WILLS SONGS. HE STILL WROTE THE ONE THAT CROWNED HIM KING FOREVER. He wrote it on a plane between Dallas and Austin. A joke, mostly — a jab at his friend Willie Nelson and the Austin crowd who figured they’d invented something new. Then he sang it inside Willie’s own building. September 27, 1974. The Texas Opry House. Willie owned the place. He said the crowd was packed so tight the fire marshal couldn’t get out. He believed nobody had heard the song before. No Nashville polish. Just pedal steel, harmonica, and Waylon grinning at his friend from the stage. He gave the Grand Ole Opry its due — then said once you cross the Red River, none of that counts. Every time he sang “Texas,” the room came apart. Here’s what almost nobody knows. Years later on TV, someone asked Waylon if he grew up a Bob Wills fan. His answer made every musician in the room laugh. It came out as a B-side. By November 1975 it was sitting at No.1 anyway. Bob Wills had died that May. The next day, his obituary ran with a verse of Waylon’s song inside it.

The Night Waylon Jennings Turned a Joke Into a Legend

Some songs arrive like confessions. Others arrive like a grin.

“Bob Wills Is Still the King” came from the second kind. Waylon Jennings later introduced it as a song he wrote on a plane between Dallas and Austin, and that detail has become part of the story because it sounds exactly like Waylon Jennings: sharp, funny, and just a little bit mischievous. The song was never meant to sound polished. It was a wink at the Texas crowd, a nod to Bob Wills, and a playful jab at the idea that Austin had somehow invented something brand new.

On September 27, 1974, Waylon Jennings performed it at the Texas Opry House in Austin, the place Willie Nelson owned. Willie Nelson later described the room as packed so tightly that even the fire marshal could not get out. It was a fitting setting for a song built on confidence and Texas pride. The audience may not have known the tune yet, but they knew the attitude immediately.

The performance landed because it had so many layers at once. It tipped its hat to Bob Wills, referenced the Grand Ole Opry, and still made room for Waylon Jennings’ plainspoken humor. There was no Nashville shine trying to soften the edges. Just pedal steel, harmonica, and a singer who sounded like he was having the time of his life standing in Willie Nelson’s own building and saying, in effect, that the old rules still mattered.

A B-Side That Would Not Stay Small

The song first appeared as the B-side to “Are You Sure Hank Done It This Way”. In the usual way of things, a B-side stays in the background. This one refused. By November 1975, the single had reached No. 1 on the country charts, and “Bob Wills Is Still the King” had already become the part listeners remembered. It was not just a regional joke anymore. It was an anthem with a grin on its face.

Years later, a television host asked Waylon Jennings whether he had grown up as a Bob Wills fan. The room laughed when Waylon Jennings answered that he was not, then added that he liked two of Bob Wills’ songs. That line mattered because it exposed the whole joke: Waylon Jennings was never pretending to be a devoted disciple. He was being honest, funny, and loyal in his own way.

Why the Song Still Feels Alive

Bob Wills had died in May 1975, and the next day an obituary ran with a verse of Waylon Jennings’ song inside it. That detail says a lot about the power of the song. It had already moved beyond novelty. It had become part of the language around Bob Wills himself.

Waylon Jennings did not build the song to flatter everyone. He built it to make a point, to tease his friend Willie Nelson, and to remind anyone listening that Texas music had a long memory. That is why the song still holds up. It sounds like a joke at first, then like history, then like a small act of love.

Every time Waylon Jennings sang it, the room seemed to come apart.

That is what great country songs sometimes do. They start as a joke on a plane and end up as the thing people remember forever.

 

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KRIS KRISTOFFERSON MADE AN ALBUM ABOUT DYING AT 76. THREE YEARS LATER HE LEARNED THE DOCTORS HAD BEEN WRONG ABOUT HIM THE WHOLE TIME. In January 2013, Kris Kristofferson released an album called Feeling Mortal. He was 76. He and producer Don Was cut twenty songs in three days and kept ten. The title song is an old man looking at his own face in the mirror, wide awake, counting what time is left. What the listeners didn’t know was why he was writing that way. For years his doctors had told him he had Alzheimer’s, or dementia from all the boxing and football of his younger days. His memory was going. His wife Lisa later said there were stretches when he couldn’t hold on to what he had just done a minute before. He was singing about the end because he had been told he was already in it. Then in February 2016, Lisa took him to a different doctor, who looked at the muscles twitching in his forearms and ordered a blood test. It came back positive for Lyme disease — a tick-borne illness the family believes he had carried for decades. It was never Alzheimer’s. Within three weeks of proper treatment, Lisa said her husband started coming back to her. Kris Kristofferson died at home on Maui on September 28, 2024, at 88 — eleven years after he made the record he thought was his goodbye.

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JOEY FEEK SANG ABOUT LEAVING HER HUSBAND BEHIND. FOUR YEARS LATER, THE MUSIC VIDEO THEY MADE BECAME THEIR REAL LIFE. On May 17, 2012, Joey + Rory filmed the video for “When I’m Gone” on their Tennessee farm. Joey sang from the point of view of a woman preparing the man she loved for life after her death. In the video, Rory was left alone in their farmhouse while Joey was imagined buried beneath the sassafras trees in their backfield. At the time, neither of them knew how painfully real those scenes would become. Joey was diagnosed with cervical cancer in 2014. After the disease returned and became terminal, she died on March 4, 2016, at just 40 years old. Rory went home without his wife — though this time, he had their little daughter Indiana beside him. Years later, Rory looked back at that old video and wrote that three and a half years after they filmed it, “that video would come true.” What had once been acting was now his life. And Joey’s voice was still there, telling him he would somehow be alright when she was gone.

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HE WAS TOO SICK TO STAND. THEN JESSI COLTER WALKED OUT — AND WAYLON SANG HIS LAST FULL CONCERT FROM A CHAIR. January 6, 2000. The Ryman Auditorium. Waylon Jennings was 62, and his health was already failing badly enough that he could no longer stand through a full show. He sat on a chair and addressed it before anyone else could. “I guess y’all noticed I’m sittin’ on this chair, and that ain’t all old age,” he told the crowd. His back and legs were hurting. Then came the old Waylon defiance: “Y’all don’t worry about me. I can still kick ass.” And he did. John Anderson, Montgomery Gentry and Travis Tritt joined him that night. But the most personal stretch came when his wife, Jessi Colter, walked out. They shared four songs — “Love’s the Only Chain,” “I’m Not Lisa,” “Storms Never Last,” and “Suspicious Minds.” “Storms Never Last” carried a different weight now. Jessi had written it years earlier, and the two had sung it together long before Waylon’s body began failing him. That night, they sang it together again. Waylon never performed another full concert. Two years later, he was gone.

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KRIS KRISTOFFERSON MADE AN ALBUM ABOUT DYING AT 76. THREE YEARS LATER HE LEARNED THE DOCTORS HAD BEEN WRONG ABOUT HIM THE WHOLE TIME. In January 2013, Kris Kristofferson released an album called Feeling Mortal. He was 76. He and producer Don Was cut twenty songs in three days and kept ten. The title song is an old man looking at his own face in the mirror, wide awake, counting what time is left. What the listeners didn’t know was why he was writing that way. For years his doctors had told him he had Alzheimer’s, or dementia from all the boxing and football of his younger days. His memory was going. His wife Lisa later said there were stretches when he couldn’t hold on to what he had just done a minute before. He was singing about the end because he had been told he was already in it. Then in February 2016, Lisa took him to a different doctor, who looked at the muscles twitching in his forearms and ordered a blood test. It came back positive for Lyme disease — a tick-borne illness the family believes he had carried for decades. It was never Alzheimer’s. Within three weeks of proper treatment, Lisa said her husband started coming back to her. Kris Kristofferson died at home on Maui on September 28, 2024, at 88 — eleven years after he made the record he thought was his goodbye.

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JOEY FEEK SANG ABOUT LEAVING HER HUSBAND BEHIND. FOUR YEARS LATER, THE MUSIC VIDEO THEY MADE BECAME THEIR REAL LIFE. On May 17, 2012, Joey + Rory filmed the video for “When I’m Gone” on their Tennessee farm. Joey sang from the point of view of a woman preparing the man she loved for life after her death. In the video, Rory was left alone in their farmhouse while Joey was imagined buried beneath the sassafras trees in their backfield. At the time, neither of them knew how painfully real those scenes would become. Joey was diagnosed with cervical cancer in 2014. After the disease returned and became terminal, she died on March 4, 2016, at just 40 years old. Rory went home without his wife — though this time, he had their little daughter Indiana beside him. Years later, Rory looked back at that old video and wrote that three and a half years after they filmed it, “that video would come true.” What had once been acting was now his life. And Joey’s voice was still there, telling him he would somehow be alright when she was gone.

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HE WAS TOO SICK TO STAND. THEN JESSI COLTER WALKED OUT — AND WAYLON SANG HIS LAST FULL CONCERT FROM A CHAIR. January 6, 2000. The Ryman Auditorium. Waylon Jennings was 62, and his health was already failing badly enough that he could no longer stand through a full show. He sat on a chair and addressed it before anyone else could. “I guess y’all noticed I’m sittin’ on this chair, and that ain’t all old age,” he told the crowd. His back and legs were hurting. Then came the old Waylon defiance: “Y’all don’t worry about me. I can still kick ass.” And he did. John Anderson, Montgomery Gentry and Travis Tritt joined him that night. But the most personal stretch came when his wife, Jessi Colter, walked out. They shared four songs — “Love’s the Only Chain,” “I’m Not Lisa,” “Storms Never Last,” and “Suspicious Minds.” “Storms Never Last” carried a different weight now. Jessi had written it years earlier, and the two had sung it together long before Waylon’s body began failing him. That night, they sang it together again. Waylon never performed another full concert. Two years later, he was gone.

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JOHNNY CASH SANG ABOUT “SEPTEMBER” WITH HIS DAUGHTER. 171 DAYS AFTER THE SONG WAS RELEASED, SEPTEMBER CAME — AND HE WAS GONE. Rosanne Cash had written “September When It Comes” years earlier, a song about growing older, letting go and finally finding rest. When she recorded it for her 2003 album Rules of Travel, her father joined her. Johnny Cash was already frail. In his verse, he sang about a man who could no longer move mountains or run the way he once had. Then came the image of being carried to a place where he could rest. The song was released on March 25, 2003. Less than two months later, Johnny lost his wife of 35 years, June Carter Cash. He kept going for a little while longer. Then, on September 12, Johnny Cash died at 71. The song had been out for 171 days. Rosanne had called it “September When It Comes.” For her father, September really did come.