The Greatest Oldies Music

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Before Nashville knew Kris Kristofferson as a songwriter, he had been a Rhodes Scholar, an Army captain, and a helicopter pilot. He gave up a planned teaching assignment at West Point to pursue music, eventually taking a janitorial job at Columbia Records. While Bob Dylan recorded nearby, Kris swept floors and emptied ashtrays. Getting Johnny Cash to record his songs took considerably longer than getting close to a recording studio. Cash knew him and had heard some of his work, but Kris was struggling to turn encouragement into a career. His marriage was unraveling, and his family saw his decision to leave the military as a disastrous mistake. Eventually, he tried an approach few songwriters could have managed: he flew a helicopter to Cash’s property and landed with a demo to deliver. The incident became Nashville folklore. In familiar versions, Kris climbed out carrying a beer and personally handed Cash “Sunday Mornin’ Comin’ Down.” Kristofferson later disputed those details. Cash wasn’t home, the tape contained a different song, and piloting a helicopter with a beer in one hand was hardly possible. The landing happened. The celebrated exchange did not. Cash’s eventual support mattered far more than the embellished story. His recording of “Sunday Morning Coming Down” reached No. 1 on the country chart in 1970, bringing Kristofferson’s writing to listeners who had never heard his name. The former officer who might have taught literature instead helped change the language of country music. Yet alongside the songs, that helicopter remained part of his story: a remarkable delivery attempt, retold so often that its passenger finally had to explain what really happened.

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KRIS KRISTOFFERSON LANDED A HELICOPTER NEAR JOHNNY CASH’S HOUSE BECAUSE NASHVILLE WOULDN’T LISTEN Kris Kristofferson had already been a Rhodes Scholar, an Army captain and a helicopter pilot when he…

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The Allman Brothers Band lost two founding members to motorcycle crashes in Macon, Georgia, barely half a mile apart. Duane Allman and Berry Oakley were both twenty-four. Duane died on October 29, 1971, just months after *At Fillmore East* established the band as one of America’s great live acts. His motorcycle collided with a truck near Hillcrest Avenue. Emergency surgery could not save him from extensive internal injuries. The surviving musicians continued as a five-piece rather than appoint another guitarist to take his place. During those difficult months, bassist Berry Oakley helped keep them together. His playing had always given their long improvisations direction, but his importance extended beyond the music. Friends remembered him as someone the others could lean on while they absorbed Duane’s absence. Then, on November 11, 1972, Berry crashed his motorcycle on Napier Avenue. One year and thirteen days had passed since Duane’s death. The proximity of the two accidents—and the fact that both men died at the same age—gave rise to talk that the band was cursed. Once again, the remaining members chose to continue. Berry had contributed to the early recording sessions for *Brothers and Sisters*. The album was completed without him, carrying his work into a chapter of the band’s career he would never see. Duane and Berry were buried beside each other at Macon’s Rose Hill Cemetery, a few miles from the roads where they suffered their fatal injuries. Their deaths came while the music they had helped create was still finding its wider audience. Within less than thirteen months, the Allman Brothers had lost both a defining guitarist and the bassist who helped hold their sound—and their friendships—together. The band continued, with the contributions of two men who never reached twenty-five remaining central to its identity.

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DUANE ALLMAN AND BERRY OAKLEY DIED THIRTEEN MONTHS APART ON NEARLY THE SAME STRETCH OF ROAD The Allman Brothers Band had only just broken through nationally when one of the…

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Mark Wright dismissed Toby Keith’s “Red Solo Cup” as stupid. That night, the song kept him awake until four in the morning. Toby was recording it in 2011, fully aware that a tribute to a plastic party cup was ridiculous. He liked that about it. Though he seldom recorded material he hadn’t written, this song had been following him around for days. His sister understood the appeal immediately. Visiting the studio during his vocal session, she laughed and said she loved it. The next day, she came back singing it. Wright, the president of Toby’s label, was harder to convince. Why would such an accomplished songwriter choose something this silly? Toby asked whether he liked it. “It’s just stupid,” Wright said. “I’m stupid sometimes myself,” Toby replied, laughing. When Wright returned the following day, he looked worn out. Toby asked what had happened. The song, Wright admitted, had kept running through his head. By 4 a.m., he had finally taken a sleeping pill because he couldn’t shake it. Toby had already experienced the same stubborn refrain. His sister had walked back into the studio singing it. Now the man questioning his judgment had lost sleep over it. Wright still thought the song was ridiculous. He had also discovered why Toby wanted to record it. What was your first reaction to “Red Solo Cup”?

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In 2011, Toby Keith was recording a song so ridiculous that even the president of his own record label couldn’t understand why a successful country star would waste time on…

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Thirty years after “Islands in the Stream,” Kenny Rogers and Dolly Parton recorded a duet that reflected the friendship they had built along the way. Released in 2013, “You Can’t Make Old Friends” gave them words for the years behind them: shared music, memories, and a familiarity neither had to explain. Their voices carried those years, too. Dolly’s gentle phrasing met Kenny’s warm, weathered delivery, making the performance feel like a conversation between people who knew each other well. The smiles and exchanged glances added to that feeling. Having already created one of country music’s best-loved partnerships, they brought an easy affection to a song about growing older and valuing the people who remember your earlier self. For listeners who had followed them since 1983, the duet offered something especially moving: the chance to hear two old friends acknowledge how much their friendship meant.

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“You Can’t Make Old Friends” is a tender meditation on a friendship shaped by decades of shared memories, reminding us that some bonds become so deeply woven into our lives…

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Loretta Lynn thought “Coal Miner’s Daughter” was missing something when she heard the studio playback: one small word. During the October 1969 sessions, she worked with producer Owen Bradley and leading Nashville musicians, singing alongside the band as much of the performance was recorded live. Listening afterward, she noticed she had left out the “yeah” she wanted before the final chorus’s declaration of pride. Engineer Jim Williamson later recalled explaining that she could simply record the word separately. “You can do that?” Loretta asked. He located an unused track, played the recording, and brought her in at the right moment. She sang the missing word, and the addition was complete. “Coal Miner’s Daughter” reached No. 1 on the country chart in 1970. Its account of Loretta’s childhood became one of her defining recordings, familiar to generations of listeners. That little “yeah” sounds entirely at home in the finished record. It took Loretta hearing its absence—and an engineer showing her what was possible—to put it there. Knowing how it happened gives that final chorus another detail to listen for.

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In October 1969, Loretta Lynn walked into a recording studio in Mount Juliet, Tennessee, to record a song about growing up in a poor coal-mining family in Kentucky. By the…

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Roy Orbison’s voice had made loneliness familiar to millions. Then, within two years, he lost his wife and two of their children. Claudette died in a motorcycle accident in June 1966. Left with three young sons, Orbison continued working while trying to care for his family. His career was already losing the momentum of “Only the Lonely,” “Crying,” and “Oh, Pretty Woman.” In 1968, while he was touring England, a fire destroyed his home near Nashville. Ten-year-old Roy Dewayne and six-year-old Anthony died. His youngest son, Wesley, survived. Orbison kept performing, particularly overseas, where audiences continued to welcome him as a major star. He later acknowledged that work helped him endure the grief. At home in America, his visibility diminished. He wrote less, and rebuilding a private life took precedence over pursuing another chart success. His return gathered strength in the 1980s. Bruce Springsteen, George Harrison, Tom Petty, and Bono were among the younger musicians who openly celebrated his influence. Television appearances introduced him to new listeners, and the Traveling Wilburys placed him alongside artists who admired him. He also completed *Mystery Girl* before dying of a heart attack in 1988, aged fifty-two. The dark glasses and extraordinary voice became enduring images of rock history. Behind them was a father and husband who had continued living and working through devastating losses. His songs had given heartbreak a sound long before listeners understood how much of it he carried himself.

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ROY ORBISON LOST HIS WIFE AND TWO SONS—THEN SOMEHOW FOUND HIS WAY BACK Roy Orbison had built a career singing about loneliness long before life gave those songs a meaning…

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Phil Kaufman believed he owed Gram Parsons one final trip to Joshua Tree. Keeping that promise led him to steal his friend’s coffin from Los Angeles International Airport. Parsons died of an overdose at the Joshua Tree Inn on September 19, 1973. He was twenty-six. His work had helped establish country rock, influencing musicians including Emmylou Harris and the Eagles, but his brief career ended in a desert town he had visited repeatedly. His family planned to fly his body east for burial. Kaufman, his road manager, remembered a different arrangement: he and Parsons had agreed that whoever died first would be cremated at Joshua Tree. With a borrowed hearse and a friend’s assistance, Kaufman persuaded airline employees that the funeral plans had changed. They collected the coffin, bought five gallons of gasoline and a case of beer, and headed into the desert. Near Cap Rock, Kaufman soaked the coffin with gasoline and ignited it. The attempt fell far short of a cremation. The fire left Parsons’ body partially burned, and authorities recovered his remains the following morning. Kaufman and his accomplice were arrested. California reportedly had no statute specifically covering the theft of a corpse, so the penalties concerned the stolen and destroyed coffin. Parsons’ remains were ultimately buried in Louisiana. The desert nevertheless became central to how fans remembered him. Decades later, visitors continued leaving flowers, guitar picks, and handwritten messages near Cap Rock. What Kaufman regarded as honoring his friend’s wishes became an extraordinary—and deeply troubling—chapter in Parsons’ story. His burial took place elsewhere, but the failed farewell bound his memory to Joshua Tree.

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GRAM PARSONS DIED IN ROOM 8 AT THE JOSHUA TREE INN. ONE DAY LATER, HIS FRIEND STOLE THE BODY FROM LAX AND DROVE IT BACK TO THE DESERT. By September…

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Marty Robbins nearly stayed home the night he entered the Country Music Hall of Fame. His son Ronny later explained that the CMA had seldom recognized his father, even with a nomination. But Eddy Arnold persuaded Marty to attend the October 1982 awards show, keeping the reason secret until he announced it on live television. Marty looked astonished. Accepting the honor, he suggested that others deserved it first, then joked that he had better take it that night because the opportunity might never come again. Eight weeks later, he was dead. There had been little sign of him stepping back. In November, he competed in the Atlanta Journal 500. On December 1, he performed in Cincinnati. The following day, he suffered another heart attack. An eight-hour operation included a quadruple bypass, but he never recovered. Marty died on December 8, 1982, aged fifty-seven, after six days in the hospital. Ronny had watched the Hall of Fame announcement on television. Remembering his father’s acceptance afterward, he heard something more unsettling in what had sounded like a passing joke. He called the words prophetic.

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On October 11, 1982, Marty Robbins stood on stage at the CMA Awards in Nashville, holding an honor he never expected to receive. He had just been inducted into the…

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John Anderson kept his health crisis from his band and much of Nashville. Jamie, his wife, lived through it beside him. Doctors later told John he had died on the operating table. Jamie told him it had happened three times. Throughout the hospital ordeal, she stayed close. They had married in 1983 and raised two daughters, Brionna and Alexa. By his Country Music Hall of Fame induction in October 2024, they had shared forty-one years of marriage. Their anniversary had been just two days earlier. Standing before the audience, John thanked the woman who had been there through it all. “She’s stood behind me through all my wavery decisions,” he said. He spoke gratefully about their years together and looked forward to each day still ahead. They had two more years. On Sunday, Jamie accompanied him down the Hall of Fame red carpet once again. By Wednesday, John had died peacefully in his sleep, aged seventy-one. Fans remembered the unmistakable voice and the songs that had accompanied their lives. His family’s announcement began closer to home, describing him first as “our beloved husband.”

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When John Anderson was in the hospital, close to losing his life, his wife Jamie Anderson stayed by his side the whole time. Afterward, doctors told him he had died…

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Merle Haggard left Ben with blunt advice: take the guitar, take the bus, and keep playing. He told his youngest son he would be an idiot to do otherwise. “Go out there and play until there’s nobody to play to.” Ben had joined the Strangers as lead guitarist at fifteen. On February 9, 2016, he played on “Kern River Blues,” his father’s final recording. Eight weeks later, Merle died on his seventy-ninth birthday. Ben returned to touring with his brother Noel and the band, bringing those songs back to the people who loved them. One became especially personal. Merle had opened a 1979 album with an autobiographical song about an entertainer giving the audience its money’s worth while carrying heartbreak onto the stage. In 2017, Ben said he understood it differently now. His father’s instructions stayed with him: “Don’t slow down, don’t lose your chops.” But preserving the songs was only part of the advice. Merle also wanted him to find his own way. “Create your own thunder.” Ten years after losing his father, Ben is still performing, carrying both instructions with him.

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The song is “Footlights,” the opening track of Merle Haggard’s 1979 album Serving 190 Proof. It was always Merle’s song about his own life on stage. But after Merle passed…

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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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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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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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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.”