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TOBY KEITH PLAYED “SHOULD’VE BEEN A COWBOY” FOR THE LAST TIME IN DECEMBER. BY SUMMER, EVERYONE WAS PLAYING IT FOR HIM. Keith sang it in Las Vegas on December 14, 2023. He died on February 5. It was his first single, out in 1993. After his death it became the song the business reached for. Brooks & Dunn did it at the CMT Awards. Carrie Underwood did it at the Opry. Luke Combs did it at the Ryman. Flatland Cavalry worked it into their set. On May 16, 2024, at the ACM Awards, Jason Aldean did it in front of Keith’s family. Blake Shelton introduced him. Aldean sat on a stool with two guitar players beside him and a string quartet behind, and slowed the whole thing down. Photographs of Keith moved across the screen while he sang. What Aldean said afterward is the part worth keeping. He said a lot of them had known Toby in different ways, and that the question going in was whether you wanted to actually feel it — or not feel it, so you could get through the performance. He chose the second. “I just didn’t want to mess it up,” he said. “I wanted to go out and give him a send-off that he deserved.” Keith’s wife texted him that night. He said that was the part that mattered: if she approved, he was fine. Aldean has been asked what he took from Keith. Not nostalgia. He said Toby spoke his mind whether it was the popular view or not, that it often cost him, and that he didn’t care.

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Toby Keith’s Last Ride Through “Should’ve Been a Cowboy” Toby Keith sang “Should’ve Been a Cowboy” in Las Vegas on…

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ON THE MORNING OF FEBRUARY 13, 2002, A 64-YEAR-OLD MAN DID NOT WAKE UP IN A HOUSE IN CHANDLER, ARIZONA. Jessi had been his wife for thirty-three years. His left foot had been gone since December. Four months earlier, country music had built him a room in Nashville with his name on the wall, and he had not gone to see it. Waylon Jennings was born outside Littlefield, Texas, in 1937, on somebody else’s farm. He had his own show on the local radio station at twelve. He quit school at sixteen. In 1958 Buddy Holly produced his first single and he was, at twenty-one, a bass player working for another man. He spent the next fourteen years being told what to do. RCA signed him in 1965 and Nashville handed him his songs, his session players, his tempos, his arrangements — the whole apparatus that decided in advance what a country record was permitted to sound like. He shared an apartment in that town with Johnny Cash and neither one of them slept much. Then in 1972 he renegotiated his contract and asked for a thing no country singer had been given: the right to choose. His own band. His own songs. His own room to cut them in. He got it, and the next ten years came out of that one sentence. Honky Tonk Heroes. Wanted! The Outlaws, the first country album ever to sell a million. Luckenbach. The song with Willie about the cowboys. He also became, improbably, the voice narrating a Friday night television show about a car, for seven seasons, to children. In October 2001 they inducted him into the Country Music Hall of Fame. He was the one living man on the list who would not turn up for it. In December they took the foot. In February he stayed in Arizona for good.

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Waylon Jennings and the Morning the Music Kept Its Promise On the morning of February 13, 2002, Waylon Jennings did…

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ON THE NIGHT OF FEBRUARY 5, 2024, A 62-YEAR-OLD MAN DID NOT MAKE IT TO MORNING IN A HOUSE IN OKLAHOMA. Tricia had been his wife for thirty-nine years. The cancer had been in his stomach since the fall of 2021. The next day, in Nashville, an anonymous panel finished counting its ballots and country music gave him a room with his name on the wall. Nobody had gotten to tell him. He had come up out of the Oklahoma oil fields with a bar band and a demo tape nobody on Music Row would take. Should’ve Been a Cowboy was released in 1993 and played three million times, more than any other country song of that decade. Six years later his label listened to the album he had just finished and kept two songs. He cut two more. They turned those down too. He asked to be dropped. Then he bought the record back with his own money — ninety-three thousand dollars for the masters of a thing he’d been told had no hit on it — and sold it to a rival for two hundred thousand. It was called How Do You Like Me Now?! It sold 3.1 million copies. When DreamWorks folded in 2005 he stopped renting rooms and opened a label of his own. On September 28, 2023, country music gave him an icon award and he sang on television with his hands shaking, and his wife cried in the audience. The song went to number one on digital sales. He booked three nights in Las Vegas that December — the tenth, the eleventh, the fourteenth. All three sold out. He posted a picture from the stage, guitar held up to the crowd. That was the last one. On February 5 he stayed in Oklahoma for good. On February 6 the ballots were counted. On October 20 his son stood up in Nashville and took the medal for him.

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The Night Toby Keith Never Saw His Final Honor On the night of February 5, 2024, Toby Keith did not…

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HE WROTE IT ABOUT GUITAR PLAYERS. HIS WIFE TOLD HIM TO CHANGE IT. In 1975, Ed Bruce was driving home from a session in Nashville. He was good at what he did and almost nobody knew it. The line that arrived was about guitar players — that’s what he was, and that’s who he thought mammas ought to warn their sons away from becoming. His wife Patsy told him to make them cowboys instead. He did. He kept the guitars inside the song anyway, one item on the list of things a boy shouldn’t grow up to pick. He recorded it himself that November. It reached number fifteen and stopped. Waylon Jennings cut his own version and couldn’t stand it. Instead of scrapping the tape he brought it into a session with Willie Nelson, who sang over what was already on it. Two voices, recorded apart, stitched into one. That version went to number one in March 1978 and sat there four weeks. It won a Grammy the following year. It became the thing people reach for when they want to explain what outlaw country was — men who wouldn’t be handled, wouldn’t be smoothed, wouldn’t do it anyone’s way but their own. It was written by a man nobody was listening to, retitled on his wife’s advice because cowboys would sell, and finished by a singer patching over a take he hated. None of which makes it less true. Ed Bruce meant every word of it before he ever wrote the word cowboy.

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He Wrote It About Guitar Players. His Wife Told Him to Change It. In 1975, Ed Bruce was driving home…

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NOBODY EVER MET HER. MILLIONS OF WOMEN SAID SHE WAS THEM. Toby Keith and Scotty Emerick met in a shared dressing room at the 1997 CMA Awards. They started playing each other songs. Over the next ten years they wrote fifty-three that Keith recorded. “Whiskey Girl” came out of that partnership, not out of a bar. Emerick has described the job plainly: they were assembling a type. A country girl with no use for wine, no patience for beer, not impressed by tequila. They wanted her good-looking and a little rough. They also set a limit — she couldn’t come across as some slobbering binge drinker. That is not a woman somebody saw across a room. That is two songwriters with a dial in front of them, turning her up until she was interesting and stopping just before she became a problem. The song works the same way. It spends most of its length on refusals — every drink she pushes away — so that by the time she accepts one, the choice is the whole character. She is built out of what she declines. DreamWorks released it on March 22, 2004, the third and final single from Shock’n Y’all. It reached number one in July. Then the part nobody engineered. Women started calling themselves whiskey girls. They still do. A character built to a spec, in a room in Nashville, walked out of that room and became a sentence real people use about themselves.

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Nobody Ever Met Her. Millions of Women Said She Was Them. “Whiskey Girl” was never the kind of song that…

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THE HIGHWAYMEN ONLY MADE THREE ALBUMS — BUT WHEN CASH, KRISTOFFERSON, NELSON, AND JENNINGS STOOD IN THE SAME ROOM, THE AIR CHANGED. Nobody built The Highwaymen in a boardroom. They came together because four men who had already survived Nashville, fame, addiction, divorce, regret, and the road somehow still had something left to say. By the time Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson recorded together in 1985, none of them needed a supergroup. That was what made it feel so dangerous. Willie still sounded like the road had no ending. Waylon still sang like permission was something other people asked for. Kris still wrote like heartbreak had gone to college and come back with a knife. Johnny still carried the weight of everything he had ever done and made it sound like a warning. Then came “Highwayman.” Each man took one verse, but it felt like each one was taking a lifetime: a bandit, a sailor, a dam builder, a starship captain. The song did not explain itself. It did not need to. You either felt the reincarnation in it, or you missed the whole point. Together they were not a reunion. They were a reckoning — four men who had each survived their own wreckage, standing in a row, singing like death was not an ending, just another road they had not ridden yet. That is why The Highwaymen still feel larger than a band. They sounded like country music looking at its own ghosts and deciding to keep driving.

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The Highwaymen: Four Legends, Three Albums, and One Unforgettable Sound The Highwaymen were never built like a marketing idea. Nobody…

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GLENN LEWIS HAD BEEN MAYOR OF MOORE, OKLAHOMA FOR DECADES. WHEN TOBY KEITH DIED, WHAT HE CHOSE TO SAY FIRST WAS THAT HE’D KNOWN HIM AS A SCHOOL-AGED BOY ROAMING THE STREETS. Moore never got the version of Toby Keith the rest of the country got. He wasn’t a star who came home for Christmas. He was the kid from Southgate — same streets, same diner, same Friday night lights. When the EF5 came through in May 2013 and killed twenty-four people, seven of them children inside Plaza Towers Elementary, he flew home. He stood in front of a camera and said the camera couldn’t cover what he’d seen. Then he filled a stadium in Norman and turned it into rebuilt houses. After that his friends had a joke. Every time the sirens went off: when’s the concert? He never said no. He kept saying yes through two years of stomach cancer, through the last shows he could stand up for. He died on a February morning in 2024. The family announced a funeral with no date and no location. Family, band, and crew. At his venue in Norman, an employee began laying out the flowers fans kept bringing, until they covered the stage he used to walk across. He was buried privately — on his own ranch, people say. Months later a stone went up in Norman, beside his father’s grave, in a cemetery where he does not lie. The town needed somewhere to go. So it built somewhere.

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Moore Remembered Toby Keith as One of Its Own When Glenn Lewis spoke after Toby Keith died in February 2024,…

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ON FEBRUARY 13, 2002, A 64-YEAR-OLD MAN DIED IN HIS SLEEP AT HIS HOUSE IN CHANDLER, ARIZONA, FOUR MONTHS AFTER COUNTRY MUSIC PUT HIS NAME ON A WALL IN NASHVILLE. Start with the bass — the instrument that exists to hold up somebody else. Waylon Jennings played bass behind Buddy Holly in 1958 and 1959. He was twenty-one, and the job was to stand at the back and make another man sound bigger. It is not a job he ever entirely quit. Nashville in those years assigned a singer his producer, his songs, and the players on his record. Waylon fought RCA for years. What he won in the early seventies was not the right to be a bigger star. It was the right to put his own road band on his own records. Those records made outlaw country. Wanted! The Outlaws was the first country album to sell a million copies, and there are four names on the cover. His biggest crossover hit is a duet. He joined a quartet with Cash, Nelson, and Kristofferson. Country music has one way of saying a man was great: take him out of the line and stand him by himself. He would not attend awards shows. He said performers should not be made to compete against each other, and he was still saying it after two Grammys and four CMAs. In October 2001 they elected him to the Country Music Hall of Fame. He did not go.

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Waylon Jennings and the Last Quiet Months Before Nashville Honored Him Start with the bass — the instrument that exists…

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ON NOVEMBER 7, 2022, A 73-YEAR-OLD MAN DIED AT A BEACH HOUSE IN DESTIN, FLORIDA, AT THE END OF TEN YEARS HE HAD SPENT MOSTLY IN PRIVATE. Start with the hands. Everything else came out of them. Jeff Cook was playing ukulele at school functions as a small boy. Guitar and keyboards in working bands by thirteen. Then the fiddle, which is a harder bargain than any of them — no frets, nothing to touch, the fingertip has to know where the note lives with nothing there to tell it. Then mandolin. Then the double-neck electric, an instrument invented for a man who wants two guitars and has one pair of hands. Every one of those asks something different of the same ten fingers. He learned all of them, and he was a tourist in none of them. He is in the Country Music Hall of Fame, the Musicians Hall of Fame, and the Fiddlers Hall of Fame. Three separate rooms, three separate skills, one man. Asked once what he would tell someone starting out, he said not to quit the first time your fingers split open. Then, in 2012, Parkinson’s. Understand what it takes, and in what order. Not the arm. The fingertip. It comes for the small precise motions first — the ones a fiddle is entirely made of — and it takes them from a man who can still walk out and stand there holding the thing. He came off the road in 2018. In 2022 he went back out and stood beside his cousins anyway. His mother outlived him.

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Jeff Cook and the Quiet Years Behind a Loud Legacy Start with the hands. Everything else came out of them.…

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THE BIGGEST SING-ALONG IN COUNTRY MUSIC IS A PARODY OF COUNTRY MUSIC. TWO FOLK SINGERS FROM CHICAGO WROTE IT. ONE OF THEM TOOK HIS NAME OFF IT BECAUSE HE WAS AFRAID OF OFFENDING COUNTRY FANS. Call it what it is, the critics say. A novelty record. Five minutes of a man ticking off every cliché in the genre — mama, trains, trucks, prison, getting drunk — and a bar full of drunks hollering along at closing time. Not a song. A joke about songs. They’re right that it’s a joke. They’re wrong about who was laughing. John Prine helped write it and then asked to be left off the credits. Not out of shame — out of respect. He thought it was too goofy, and he didn’t want to insult the country community. He wouldn’t even take the royalties. So Steve Goodman took his own money and bought Prine a 1942 Wurlitzer jukebox instead. David Allan Coe cut it in 1975 and got the first Top 10 of his life out of it. And in 2023, Prine’s family gave that jukebox to the Country Music Hall of Fame — where it sits today. A song that made fun of country music ended up enshrined inside it. Still think it’s just a joke?

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The Joke That Country Music Took to Heart How a parody became one of the biggest sing-alongs in the genre…

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HE WOULD BECOME ONE OF COUNTRY MUSIC’S MOST FAMOUS OUTLAWS. SHE GREW UP PLAYING PIANO IN HER PREACHER MOTHER’S CHURCH. When Jessi Colter married Waylon Jennings in 1969, he already had three marriages behind him and years of hard living ahead. There were pills. Later, cocaine. Long nights on the road, addiction, and the kind of chaos that eventually became part of the Waylon Jennings legend. Jessi came from a different world. Her mother was a Pentecostal minister, and Jessi had been singing and playing piano in church since childhood. Their marriage was never a fairy tale. Jessi later spoke openly about how close Waylon’s addiction came to destroying what they had. But the marriage survived. By the end of 2001, diabetes had become so severe that Waylon’s left foot was amputated. Less than two months later, on February 13, 2002, he died in his sleep at their Arizona home. Jessi was still his wife after more than 32 years. Years later, she released *The Psalms*, music drawn from the faith she had carried since childhood. Not every love story ends with a song. Some end with a prayer.

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BILLY JOE SHAVER’S SON DIED TWO DAYS BEFORE HE WAS SUPPOSED TO BEGIN THE SOLO ALBUM HE HAD WAITED YEARS TO MAKE. Eddy Shaver spent most of his career beside his father. He was the fire behind Billy Joe’s songs, a gifted guitarist who also played with artists including Dwight Yoakam and Willie Nelson while recording acclaimed albums with his dad as Shaver. But Eddy wanted something of his own. In late December 2000, he signed a solo deal with Antone’s Records. He was scheduled to begin recording a new U.S. solo album on January 2, 2001. He never made it. Eddy was found unconscious in a Waco hotel room and died early on December 31. He was 38. Billy Joe had spent years standing beside his only son onstage. Eddy was finally about to make a record with his own name out front. He died just two days before the sessions were supposed to begin.

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Years after Waylon Jennings died, Jessi Colter said people still liked to remember the darkest years — but she remembered what happened after them. She never pretended those years were easy. Waylon’s drug use frightened her. He tried more than once to stop, and Jessi eventually reached a point where she knew she could not simply stand by and watch. Then something changed. Jessi said that when Waylon finally pulled himself out of that life, “he never touched anything again.” And she remembered a promise he made afterward: “I’m making a mark for the good for the rest of my life.” She believed he kept it. Waylon died on February 13, 2002, at 64. By then, the roughest years of his life had become the part of his story people loved to repeat. But Jessi remembered what came next. Waylon got out. And when he promised to spend the rest of his life doing good, she believed he did exactly that.

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The night before Chet Atkins was laid to rest, Jerry Reed called Steve Wariner and talked about Chet for 45 minutes. But when the funeral came, Jerry couldn’t make himself go. Chet died at his Nashville home on June 30, 2001. He was 77. For Jerry, he had been far more than another great guitarist. Chet had helped bring him to RCA, encouraged him to stop trying to sound like everyone else, and became one of his closest musical partners. They spent decades trading guitar lines, recording together, and pushing each other into places few players could follow. Chet even said Jerry had taken the fingerstyle approach farther than he had. The night before Chet’s service, Jerry poured all of that into a phone call with Wariner. Then came the next day. Jerry simply told him, “I can’t do it.” For a man who could usually turn anything into a joke, losing Chet apparently left him with nothing funny to say.