The Greatest Oldies Music

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Toby Keith ended 2023 thanking the people beside him and looking ahead to another year. He would die thirty-six days later. On December 31, he posted a photograph with his band and crew, writing: “Been one hell of a year with a lot to be grateful for. Here’s to 2024!” After more than two years of treatment for stomach cancer, he still had plans. In a November interview, Toby said he was feeling better and had come off chemotherapy. He spoke plainly about continuing, despite the uncertainty. “If I live to be 100 or I don’t, I’m going to go forward.” On February 5, 2024, he died peacefully at sixty-two, surrounded by his family. His New Year’s post was written without knowing how little time remained. Read afterward, its gratitude feels especially poignant: Toby was welcoming the future while appreciating the people who had helped him reach it.

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On December 31, 2023, Toby Keith shared a New Year’s message that seemed full of hope for the months ahead. After more than two years of cancer treatments, the Oklahoma…

Country

Jerry Reed’s return to No. 1 came through a divorce story—and a husband with plenty to complain about. Nine years and fifteen charting singles had passed since “Lord, Mr. Ford” topped the country chart in 1973. Jerry remained busy making records, performing, and appearing in movies, but none of those singles had taken him back to the summit. In 1982, he recorded a Tim DuBois song with producer Rick Hall at Alabama’s FAME Studios. Its narrator was a newly divorced man tallying up everything he had lost, with each complaint adding to the joke. Jerry’s delivery made the most of it. His conversational phrasing and comic timing gave the husband’s increasingly outrageous grievances a personality listeners couldn’t miss. That September, the record spent two weeks at No. 1 on Billboard’s country chart. It would be Jerry’s final country chart-topper. After nearly a decade, a song about losing almost everything had given him another hit. Can you name the Jerry Reed song that reached No. 1 in 1982?

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For nine years, Jerry Reed had been waiting for another No. 1 country hit. Fifteen charting singles had come and gone since “Lord, Mr. Ford” topped the country chart in…

Country

George Jones had not spoken for days when, according to Nancy, he opened his eyes and offered one last introduction. She was near the foot of his hospital bed with a doctor when he said: “Well, hello there. I’ve been looking for you. My name’s George Jones.” Then he closed his eyes. Nancy believed he was greeting God. George died on April 26, 2013, aged eighty-one, after thirty years of marriage to Nancy. He had also prepared words for two family members he would never meet. Before his death, he wrote a letter to the twins his granddaughter Jennifer was expecting. The babies were born that August, more than three months after he died. Millions of listeners could come to know George through his records. His great-grandchildren would have those songs, too, along with a letter addressed to them—written while he was still here, waiting for their arrival.

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In the final moments of George Jones’s life, Nancy Jones heard a familiar voice break the silence of a hospital room. Nancy Jones later recalled standing near the foot of…

Country

By the time Loretta Lynn began singing professionally, she had already held a demanding job: cooking and cleaning for thirty-six ranch hands while raising four children. She and her husband, Doo, were living in Washington State, a long way from her Kentucky childhood. Both worked to cover the rent, and Loretta’s days revolved around the farmhouse, meals, chores, and the needs of their young family. Doo’s gift of a seventeen-dollar Sears guitar opened another possibility. She taught herself to play and started performing nearby. For material, she could draw on experiences she already understood. In 1960, she recorded her debut single, “I’m a Honky Tonk Girl.” Years later, speaking with NPR, Loretta recalled the workload that had come before her recording career. Compared with feeding ranch hands, keeping house, and caring for four children, performing offered a different kind of work. Her verdict came with characteristic humor: “And so singing was easy.”

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Before Loretta Lynn became one of country music’s most recognizable voices, there were four children to raise, a farmhouse to care for, and 36 ranch hands who needed meals cooked…

Country

Long before Loretta Lynn shared a stage with Kitty Wells, she treasured a much smaller encounter: touching the fabric of Kitty’s stage dress. Loretta and her husband had gone to hear her perform in Washington state. Afterward, they found Kitty heading toward her bus, carrying the dress she had worn. Loretta later remembered reaching out to feel it. She admired Kitty so much that she tried to sing like her wherever she performed. By the 1988 CMA Awards, Loretta was standing beside her hero, joining Kitty, Brenda Lee, and k.d. lang for a medley of country classics. Their studio collaboration for lang’s *Shadowland* album earned a Grammy nomination the following year. Kitty had helped make such careers possible. In 1952, she became the first female solo artist to reach No. 1 on the country chart. For Loretta, singing together marked an extraordinary distance traveled from that meeting beside the bus. Which of those four voices holds the most memories for you?

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In 1988, Loretta Lynn stood onstage at the Country Music Association Awards beside Kitty Wells, Brenda Lee, and k.d. lang. Four remarkable women were sharing a moment that celebrated the…

Country

Vern Gosdin was earning his living in Georgia’s glass business when he decided to pay for another chance at music. In 1976, he traveled to Nashville and financed a recording session himself. He had already spent years performing and recording, including with his brother Rex, but a successful solo career remained out of reach. Among the songs he chose was “Hangin’ On,” which the Gosdin Brothers had recorded in 1967. His longtime friend Emmylou Harris supplied harmonies on the new version and on “Yesterday’s Gone.” Gosdin later recalled recording just three or four songs before returning home. Within days, he said, four labels had shown interest. He signed with Elektra. “Hangin’ On” climbed to No. 16 on the country chart. “Yesterday’s Gone” followed, reaching the Top 10 and giving his solo career the momentum he had struggled to find. After years of making a living elsewhere, Gosdin was back on country radio. Before a label committed to him, he had committed his own money to a few songs he still wanted people to hear.

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In 1976, Vern Gosdin was making his living in the glass business in Georgia when he decided to spend his own money on a recording session in Nashville. There was…

Country

Vince Gill asked Gene Watson for one more song, explaining that a cold had left him needing a short vocal rest. Gene had no idea what was coming. It was January 17, 2020, at Nashville’s sold-out Ryman Auditorium. Gene had finished two numbers when Vince made his request: sing “Farewell Party”—and accept an invitation to join the Grand Ole Opry. The surprise nearly took Gene’s legs out from under him. “I’m not sure I have anything left after that kind of surprise,” he said. But he sang, and the audience rose to its feet. Afterward, Gene admitted he had been so overwhelmed that he couldn’t be certain he had hit the right notes. Decades of performing hadn’t prepared him for receiving that invitation just before delivering his signature song. He had expected another evening onstage. Instead, he found himself singing “Farewell Party” at the moment he was welcomed into the Opry family.

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Vince Gill said a little cold had left his voice needing a rest. Would Gene Watson sing another song? That was how Gene Watson later remembered the beginning of an…

Country

A morning Johnny Cash described in 1970 became a duet in 2018. Its video brought the story back to the place where it began—the remains of his home with June. That February, June Carter Cash was eight months pregnant with their son, John Carter. Johnny wrote about making coffee in their lakeside house in Hendersonville, Tennessee, hearing her come downstairs, and sitting together. His affection came through in the small details of an ordinary day. Years later, Ruston Kelly discovered the passage in a Cash book while still a teenage songwriter. He set it to music and kept the melody. When John Carter began assembling *Johnny Cash: Forever Words*, Kelly returned to the song, recording it with Kacey Musgraves. Released in April 2018, “To June This Morning” gave Johnny’s words two voices. By then, both Johnny and June had been gone for fifteen years. Their house had burned down in 2007, and the video was filmed among what remained of the Hendersonville property. The home was gone, but the writing preserved a moment inside it: coffee being made, footsteps approaching, and the quiet pleasure of June’s company.

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In February 1970, Johnny Cash wrote something for June Carter Cash that had nothing to do with fame, concerts, or life on the road. The words described a simple morning…

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Thirty-six dollars was the price Dion remembered from his parents’ rent in the Bronx. According to his later account, it was also the reason he declined a seat on Buddy Holly’s plane. On February 2, 1959, the Winter Dance Party tour reached Clear Lake, Iowa. The musicians had endured freezing journeys aboard unreliable buses, and Holly chartered a small aircraft to get to the next stop. Its three passenger seats offered a welcome escape from another night on the road. Dion recalled that he and J.P. “The Big Bopper” Richardson secured places during a backstage discussion at the Surf Ballroom. Then Holly mentioned the fare. For Dion, $36 carried memories of household bills and his parents arguing about money. Spending the equivalent of a month’s rent on a short flight felt impossible to justify. In his telling, he stepped aside, and seventeen-year-old Ritchie Valens took the seat. Shortly after 1 a.m. on February 3, the plane departed. Minutes later, it crashed into a cornfield, killing Holly, Valens, Richardson, and pilot Roger Peterson. Investigators cited weather conditions and the pilot’s loss of control. Dion continued the remaining tour dates by bus. He later described repeatedly trying to make sense of the deaths and the circumstances that had kept him off the aircraft. Accounts of how the seats were allocated differ, and Dion’s version remains one of the disputed parts of that night’s history. His recollection, however, centered on a precise detail: the fare. He said he had declined because he could not separate the cost of that flight from what it had once taken to keep a roof over his family.

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DION GAVE UP HIS SEAT ON BUDDY HOLLY’S PLANE BECAUSE $36 FELT LIKE A MONTH’S RENT Dion had already won a seat on Buddy Holly’s chartered plane when he heard…

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Billy Joe Shaver spent three years defending a shooting that would eventually become part of his songwriting. In 2007, he stopped at Papa Joe’s Texas Saloon in Lorena, near Waco, with his former wife, Wanda. An argument with another patron, Billy Coker, moved outside. Shaver fired a .22 pistol, striking Coker in the face. What led to that shot became the central question at his 2010 trial. Witnesses testified that Shaver had asked Coker where he wanted to be shot. Shaver gave a different account: he believed Coker was reaching for a weapon and feared he would be killed. He maintained that he had acted in self-defense. The proceedings drew attention well beyond Texas. Willie Nelson and Robert Duvall were among the friends who attended in support. After hearing the evidence, the jury acquitted Shaver of aggravated assault. Outside court, he expressed regret that the confrontation had happened. Then came a characteristically unsettling joke: perhaps he and Coker could become friends, and Coker might return his bullet. Shaver later revisited the incident in “Wacko From Waco,” bringing a real shooting into a catalog already filled with trouble, survival, and difficult reckonings. His life had supplied plenty of those before Lorena. He had lost fingers in a sawmill accident, survived a major heart attack, and mourned both his wife and his son. His writing had also helped give Waylon Jennings’ outlaw era its voice. The trial added another complicated episode to that history. For listeners accustomed to hearing Shaver’s experiences transformed into songs, this one came with testimony, conflicting accounts, and a verdict before it ever reached a record.

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BILLY JOE SHAVER SHOT A MAN OUTSIDE A TEXAS BAR—THEN TURNED THE TRIAL INTO A SONG In 2007, Billy Joe Shaver walked outside a Texas bar after an argument and…

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Country

Toby Keith ended 2023 thanking the people beside him and looking ahead to another year. He would die thirty-six days later. On December 31, he posted a photograph with his band and crew, writing: “Been one hell of a year with a lot to be grateful for. Here’s to 2024!” After more than two years of treatment for stomach cancer, he still had plans. In a November interview, Toby said he was feeling better and had come off chemotherapy. He spoke plainly about continuing, despite the uncertainty. “If I live to be 100 or I don’t, I’m going to go forward.” On February 5, 2024, he died peacefully at sixty-two, surrounded by his family. His New Year’s post was written without knowing how little time remained. Read afterward, its gratitude feels especially poignant: Toby was welcoming the future while appreciating the people who had helped him reach it.

Country

Jerry Reed’s return to No. 1 came through a divorce story—and a husband with plenty to complain about. Nine years and fifteen charting singles had passed since “Lord, Mr. Ford” topped the country chart in 1973. Jerry remained busy making records, performing, and appearing in movies, but none of those singles had taken him back to the summit. In 1982, he recorded a Tim DuBois song with producer Rick Hall at Alabama’s FAME Studios. Its narrator was a newly divorced man tallying up everything he had lost, with each complaint adding to the joke. Jerry’s delivery made the most of it. His conversational phrasing and comic timing gave the husband’s increasingly outrageous grievances a personality listeners couldn’t miss. That September, the record spent two weeks at No. 1 on Billboard’s country chart. It would be Jerry’s final country chart-topper. After nearly a decade, a song about losing almost everything had given him another hit. Can you name the Jerry Reed song that reached No. 1 in 1982?

Country

George Jones had not spoken for days when, according to Nancy, he opened his eyes and offered one last introduction. She was near the foot of his hospital bed with a doctor when he said: “Well, hello there. I’ve been looking for you. My name’s George Jones.” Then he closed his eyes. Nancy believed he was greeting God. George died on April 26, 2013, aged eighty-one, after thirty years of marriage to Nancy. He had also prepared words for two family members he would never meet. Before his death, he wrote a letter to the twins his granddaughter Jennifer was expecting. The babies were born that August, more than three months after he died. Millions of listeners could come to know George through his records. His great-grandchildren would have those songs, too, along with a letter addressed to them—written while he was still here, waiting for their arrival.

Country

By the time Loretta Lynn began singing professionally, she had already held a demanding job: cooking and cleaning for thirty-six ranch hands while raising four children. She and her husband, Doo, were living in Washington State, a long way from her Kentucky childhood. Both worked to cover the rent, and Loretta’s days revolved around the farmhouse, meals, chores, and the needs of their young family. Doo’s gift of a seventeen-dollar Sears guitar opened another possibility. She taught herself to play and started performing nearby. For material, she could draw on experiences she already understood. In 1960, she recorded her debut single, “I’m a Honky Tonk Girl.” Years later, speaking with NPR, Loretta recalled the workload that had come before her recording career. Compared with feeding ranch hands, keeping house, and caring for four children, performing offered a different kind of work. Her verdict came with characteristic humor: “And so singing was easy.”