The Greatest Oldies Music

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The day after John Denver died, Annie Martell named her favorite of his love songs. It wasn’t “Annie’s Song,” the ballad that had made her name familiar to millions. It was “Perhaps Love.” John and Annie married in 1967. Years later, following a difficult stretch in their relationship, he went skiing in Aspen. On a chairlift, the words to “Annie’s Song” began coming to him. He returned home and wrote what became one of the defining love songs of the 1970s. Annie later said hearing it could still bring her to tears. But the devotion it captured could not spare their marriage. They separated in 1982 and divorced. As their relationship was coming apart, John wrote “Perhaps Love” for her. On October 12, 1997, John died in a plane crash at 53. Interviewed the following day, fifteen years after their separation, Annie chose that quieter reflection on love as her favorite. “Annie’s Song” preserved a moment when he felt close to her. The song she treasured most came from the painful years when they were struggling to hold on.

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The Shattered Monument of Love and the Song Annie Martell Cherished Most A Marriage Born from the Anthem of “Annie’s Song” In 1967, John Denver and Annie Martell stepped into…

Country

John Anderson went into a writing session in June 2018 without knowing whether he could still make a record. The song he helped finish that day eventually gave his final studio album its name. A serious illness during 2017 and 2018 had affected his hearing and left him uncertain about singing again. When Dan Auerbach invited him to write with David Ferguson and Pat McLaughlin, an Anderson album wasn’t part of the arrangement. McLaughlin brought an idea about how quickly life passes. In roughly ninety minutes, the four men wrote “Years.” Anderson was so pleased with the result that he called Auerbach that evening. When Auerbach later proposed making a full album, Anderson hesitated. His confidence had not recovered alongside his health. Auerbach and Ferguson, however, believed his voice was ready. *Years* arrived on April 10, 2020. What began as a writing session had brought Anderson back into the studio for an album he once doubted he could make. After his death on October 21, 2026, at 71, the title song took on another significance. For listeners who had grown older with his records, its reflection on passing time now belonged to the voice they would miss.

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John Anderson’s final studio album began at a time when the country music legend wasn’t even sure another album was possible. After a serious illness left John Anderson struggling with…

Country

Brad Paisley remembers proposing to Kimberly Williams at the end of a pier in Venice, Los Angeles, with nobody else around. Kimberly remembers the location a little more precisely: right outside the public toilets. It was 2002, more than a decade after Brad first noticed her onscreen in *Father of the Bride*. He had been watching it in a West Virginia theater in 1991—on a date with another girl. Ten years later, he invited Kimberly to appear in his “I’m Gonna Miss Her” video. Her manager apparently spotted the romantic possibilities early. By November, Brad and Kimberly were dating. The pier became special to them during a walk months before the proposal. At its far end, Brad had told her he believed they were meant to be together. When he bought a ring, he knew where he wanted to ask. He later confessed that the secluded spot offered some reassurance, too: if she went running back down the pier, there would be few witnesses. Kimberly stayed, said yes—and kept the detail that makes their engagement story unmistakably theirs.

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Brad Paisley has told the story of his proposal more than once, and his version is simple. He surprised Kimberly Williams, and the two of them were completely alone out…

Country

The last time Waylon Jennings saw Buddy Holly, his friend was laughing. Their farewell joke would haunt Waylon for years. In February 1959, Waylon was playing bass in Buddy’s band. When an ailing J.P. “The Big Bopper” Richardson asked to escape another freezing journey on the tour bus, Waylon gave him his seat on the chartered plane. Before leaving, Buddy teased that he hoped Waylon’s bus would freeze. Waylon answered with a joke of his own: he hoped Buddy’s plane would crash. Hours later, Buddy, Richardson, Ritchie Valens and the pilot were dead. Don McLean would later immortalize the tragedy in “American Pie” as “the day the music died.” Waylon carried the memory of those careless words—and the loss of someone who had believed in his talent long before Nashville knew his name. Seventeen years later, he wrote “Old Friend.” The tribute reached beyond the crash to the person he remembered: Buddy laughing as they said goodbye, before either knew it was their last farewell.

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Don McLean turned Buddy Holly’s death into one of the most famous moments in American music with “American Pie.” But for Waylon Jennings, February 3, 1959, was never just the…

Country

When organizers suggested touring partners to Waylon Jennings in 1983, he already knew whom he wanted: Jerry Reed. Their friendship reached back to Waylon’s early recording sessions at RCA, where Chet Atkins had recruited Jerry to play guitar. Waylon remembered how much Jerry seemed to enjoy his music. That enthusiasm helped him feel more at ease in the studio. Nearly twenty years later, the comfort between them remained. Speaking to Country Music magazine about the proposed tour, Waylon said no other performer made him feel so relaxed at work. Jerry was equally enthusiastic. Recording together again, he said, had been as much fun as their early sessions. That summer, they embarked on a 27-city tour and released their duet, “Hold On, I’m Comin’.” Waylon saw no rivalry in the partnership. Jerry brought out his best, making the choice of a touring companion an easy one. “There’s nobody else that I’d rather be on stage with than ole Jerry.”

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By the summer of 1983, Waylon Jennings had spent years building a reputation as one of country music’s most independent performers. Waylon Jennings had shared records and stages with some…

Country

When Billy Joe Shaver tried to repay Willie Nelson for burying his only son, Willie would not take the money. Eddy Shaver died on New Year’s Eve 2000, at 38. He had spent years playing guitar alongside his father, recording with him as Shaver and co-writing “Live Forever.” Billy Joe had already buried his wife, Brenda, and his mother in 1999. Losing Eddy meant losing both his child and his closest musical partner. A show near Austin was still on the calendar that night. Unable to find his band, Billy Joe turned to Willie, who assembled musicians and carried most of the performance himself. Billy Joe joined him for a few songs. Afterward, Willie brought him home, and they talked through the night. He gave Billy Joe money and paid Eddy’s burial expenses, offering practical help when his friend was overwhelmed by grief. When money later came through from Sony, Billy Joe wanted to settle the debt. Willie refused repayment. Speaking with Terry Gross in 2005, Billy Joe credited Willie with helping him find his way back into the world. Their friendship stretched back to the 1950s. Decades later, when Billy Joe needed help getting through a night he could scarcely face, Willie stayed beside him—and kept helping after the music stopped.

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Willie Nelson paid for the burial of Billy Joe Shaver’s only son. When Billy Joe Shaver later tried to repay the money, Willie Nelson refused to accept it. But that…

Country

Three days after June Carter Cash’s funeral, Johnny Cash returned to the recording studio. He was following something she had asked of him: “If something happens to me, you keep working.” June died on May 15, 2003. To some, his return seemed painfully soon. But in an interview weeks later, Johnny explained that making music was how he hoped to get through the loss. With producer Rick Rubin’s help, he continued recording as his own health deteriorated. His condition determined what each day allowed. Sometimes he could sing; sometimes he was too ill to work. Johnny died on September 12, less than four months after June. Some of the recordings from that final period reached listeners years later. In those months, the studio gave him work he could still do and a way to honor her wishes. June had asked him to keep going, and whenever his strength allowed, he did.

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When June Carter Cash passed away on May 15, 2003, Johnny Cash lost the woman who had shared more than 35 years of marriage, music, and life with him. For…

Country

The hospital bill named “Mrs. Connie Nelson.” Willie Nelson’s wife, Shirley Collie, had never heard of her. When the bill reached their home in 1969, it revealed charges for the birth of Paula Carlene, Willie’s daughter with Connie Koepke. He had been seeing Connie for several years while still married to Shirley. Willie later recalled being confronted with the paperwork and having no explanation that could conceal what had happened. His daughter Lana remembered two discoveries unfolding at once: Shirley learned about another woman, and Lana learned she had another sister. Willie and Shirley divorced in 1971. He married Connie that same year, and they later welcomed another daughter, Amy. Connie also helped bring his older children into a household shaped by earlier marriages, separations and long absences on the road. Paula later acknowledged that the adjustment was difficult for her older half-siblings, though Willie eventually worked to keep his children connected. During those same years, his career was changing direction. His Tennessee house burned in 1970, and he returned to Texas as his Nashville life unraveled. Austin offered room for the musical freedom he had struggled to find. *Shotgun Willie*, *Red Headed Stranger* and his Fourth of July Picnics helped establish him as a central figure in outlaw country. For listeners, that period became a story of artistic independence. For his family, it also involved betrayal and the difficult work of rebuilding relationships. Willie later acknowledged the hurt he had caused Martha, Shirley and Connie rather than attempting to explain it away. His children eventually shared recordings and stages with him, but becoming that extended family took time. Behind the familiar image of everyone gathered around Willie were people who had lived through the consequences of choices he could no longer undo.

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A HOSPITAL BILL EXPOSED WILLIE NELSON’S SECRET FAMILY A hospital bill arrived at Willie Nelson’s house in 1969. It was addressed to “Mrs. Connie Nelson.” It included charges connected to…

Country

Dolly Parton wanted nothing more than to hear Elvis Presley sing “I Will Always Love You.” Then Colonel Tom Parker explained what that opportunity would cost: half the song’s publishing rights. Turning him down left her devastated. Dolly later recalled crying all night, knowing she had refused a chance many songwriters would have accepted without hesitation. But she understood the lasting value of owning her work, even when protecting it meant disappointing one of her musical heroes. She had written the song as a farewell to Porter Wagoner while preparing to leave his television show and build her solo career. Her recording reached No. 1 on the country chart in 1974. In 1982, she recorded it again for *The Best Little Whorehouse in Texas* and took it to the top a second time. Then Whitney Houston recorded it for *The Bodyguard* in 1992. Her performance introduced the song to an enormous worldwide audience and became one of the era’s biggest-selling singles. Dolly still owned the rights she had been asked to surrender years earlier. She never stopped wishing she could have heard Elvis’s interpretation. That disappointment remained, even as Whitney’s success demonstrated how much her decision had protected. At the time, Dolly had no way of knowing what another singer would eventually do with her song. She simply believed it was worth keeping—and accepted a painful evening rather than sign away half its future. Would you have given Elvis half the publishing rights for the chance to hear him sing it?

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DOLLY PARTON CRIED AFTER SAYING NO TO ELVIS—THEN WHITNEY HOUSTON PROVED WHY SHE HAD TO Dolly Parton was preparing for the thrill of hearing Elvis Presley record one of her…

Country

Garth Brooks promised his three daughters he would stay home until the youngest was ready for college. Keeping that promise meant stepping back from one of the biggest careers country music had ever seen. By 2001, he had spent a decade filling arenas and sending eight albums to No. 1 on the Billboard 200. Away from the crowds, he was dealing with losses success could do little to soften. His mother died of cancer in 1999, and his marriage to Sandy Mahl came apart after fourteen years. Their daughters were just nine, seven and five. Brooks returned to Oklahoma and began building his days around raising them. School calendars and time at home took priority over another album campaign or tour. When Steve Wynn offered him a Las Vegas residency in 2009, Brooks agreed only after the weekend schedule was arranged around his family commitments. He explained that he was still only halfway through the work he had retired to do. In 2014, his youngest daughter turned eighteen and headed to college. With that milestone reached, Brooks resumed full-scale touring, thirteen years after stepping away. His career had been defined by extraordinary numbers: record sales, chart positions and packed arenas. During those years in Oklahoma, he kept track of something more personal—the time he had promised his daughters, and whether he was there to share it.

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GARTH BROOKS WALKED AWAY FROM COUNTRY MUSIC TO KEEP A PROMISE TO HIS DAUGHTERS By 2001, Garth Brooks had spent most of a decade making country music look enormous. Arenas.…

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You Missed

Country

The day after John Denver died, Annie Martell named her favorite of his love songs. It wasn’t “Annie’s Song,” the ballad that had made her name familiar to millions. It was “Perhaps Love.” John and Annie married in 1967. Years later, following a difficult stretch in their relationship, he went skiing in Aspen. On a chairlift, the words to “Annie’s Song” began coming to him. He returned home and wrote what became one of the defining love songs of the 1970s. Annie later said hearing it could still bring her to tears. But the devotion it captured could not spare their marriage. They separated in 1982 and divorced. As their relationship was coming apart, John wrote “Perhaps Love” for her. On October 12, 1997, John died in a plane crash at 53. Interviewed the following day, fifteen years after their separation, Annie chose that quieter reflection on love as her favorite. “Annie’s Song” preserved a moment when he felt close to her. The song she treasured most came from the painful years when they were struggling to hold on.

Country

John Anderson went into a writing session in June 2018 without knowing whether he could still make a record. The song he helped finish that day eventually gave his final studio album its name. A serious illness during 2017 and 2018 had affected his hearing and left him uncertain about singing again. When Dan Auerbach invited him to write with David Ferguson and Pat McLaughlin, an Anderson album wasn’t part of the arrangement. McLaughlin brought an idea about how quickly life passes. In roughly ninety minutes, the four men wrote “Years.” Anderson was so pleased with the result that he called Auerbach that evening. When Auerbach later proposed making a full album, Anderson hesitated. His confidence had not recovered alongside his health. Auerbach and Ferguson, however, believed his voice was ready. *Years* arrived on April 10, 2020. What began as a writing session had brought Anderson back into the studio for an album he once doubted he could make. After his death on October 21, 2026, at 71, the title song took on another significance. For listeners who had grown older with his records, its reflection on passing time now belonged to the voice they would miss.

Country

Brad Paisley remembers proposing to Kimberly Williams at the end of a pier in Venice, Los Angeles, with nobody else around. Kimberly remembers the location a little more precisely: right outside the public toilets. It was 2002, more than a decade after Brad first noticed her onscreen in *Father of the Bride*. He had been watching it in a West Virginia theater in 1991—on a date with another girl. Ten years later, he invited Kimberly to appear in his “I’m Gonna Miss Her” video. Her manager apparently spotted the romantic possibilities early. By November, Brad and Kimberly were dating. The pier became special to them during a walk months before the proposal. At its far end, Brad had told her he believed they were meant to be together. When he bought a ring, he knew where he wanted to ask. He later confessed that the secluded spot offered some reassurance, too: if she went running back down the pier, there would be few witnesses. Kimberly stayed, said yes—and kept the detail that makes their engagement story unmistakably theirs.

Country

The last time Waylon Jennings saw Buddy Holly, his friend was laughing. Their farewell joke would haunt Waylon for years. In February 1959, Waylon was playing bass in Buddy’s band. When an ailing J.P. “The Big Bopper” Richardson asked to escape another freezing journey on the tour bus, Waylon gave him his seat on the chartered plane. Before leaving, Buddy teased that he hoped Waylon’s bus would freeze. Waylon answered with a joke of his own: he hoped Buddy’s plane would crash. Hours later, Buddy, Richardson, Ritchie Valens and the pilot were dead. Don McLean would later immortalize the tragedy in “American Pie” as “the day the music died.” Waylon carried the memory of those careless words—and the loss of someone who had believed in his talent long before Nashville knew his name. Seventeen years later, he wrote “Old Friend.” The tribute reached beyond the crash to the person he remembered: Buddy laughing as they said goodbye, before either knew it was their last farewell.