The Greatest Oldies Music

November 2026

Country

The business card Alan Jackson kept in his billfold began with a conversation he wasn’t there to hear. His wife, Denise, was working as a flight attendant when she spotted Glen Campbell waiting for a flight at the Atlanta airport. Back in Georgia, Alan was still an unknown singer hoping to build a career in Nashville. Denise approached Glen and explained her husband’s ambition. Could he help? “Is he any good?” Glen asked, looking directly at her. She assured him Alan was both a good singer and a good songwriter. Glen handed her his card. That introduction eventually brought Alan to Glen’s Nashville publishing company, where he secured his first songwriting deal for $100 a week. Glen later joked that the modest paycheck was intentional: a few hard times would give the young writer something to write about. For years, Alan carried the card as a good-luck charm. He also understood how much depended on Denise having the nerve to start that conversation. Without her approaching Glen, he admitted, he might still have been driving a forklift.

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Long after he became a star, Alan Jackson kept one small piece of paper in his billfold. It was not a lucky coin or a family photo. It was a…

Country

Kris Kristofferson could write for an audience of strangers. Writing a song for Johnny Cash—and singing it to him over dinner—frightened him. June Carter had made the request after Johnny returned from rehabilitation. She was inviting close friends, including Waylon Jennings and Jessi Colter, and wanted Kris to bring her husband something personal. Johnny had encouraged him during his difficult early Nashville years. Finding words for that friendship felt unusually exposing. Kris finished “Good Morning John” and performed it at the gathering, later recalling his embarrassment and guessing Johnny had felt much the same. An attempt to record it with Willie Nelson brought a different reaction. The supporting voices were meant to repeat Kris’s lines. When he sang, “I love you, John,” Willie replied, “He loves you, John.” Kris laughed so hard the recording fell apart. Waylon released his version in 1985. Kris waited until 2009 to include his own on an album, six years after Johnny’s death. The song began as June’s request for a dinner among friends. It endured as Kris’s way of thanking someone whose support had mattered long before he became successful. Have you heard his recording of “Good Morning John”?

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Kris Kristofferson had written songs that touched millions of people. But when June Carter asked Kris Kristofferson to write something especially for Johnny Cash, the legendary songwriter admitted that the…

Oldies Musics

Nine of the ten best-selling country songs belonged to Toby Keith on Billboard’s chart dated February 17, 2024. No artist had achieved that before. Following his death on February 5 at sixty-two, listeners returned to songs spanning his career. “Should’ve Been a Cowboy” ranked third, followed by “Courtesy of the Red, White and Blue” at fourth. “Beer for My Horses,” “American Soldier,” and “Red Solo Cup” also appeared in the Top 10. Luke Combs’s “Fast Car,” at No. 2, was the only interruption. Leading them all was “Don’t Let the Old Man In,” which sold 27,000 downloads during the tracking week. Toby wrote it after speaking with Clint Eastwood in 2018. Five years later, he performed it at the People’s Choice Country Awards while undergoing cancer treatment. That September 2023 appearance helped send it to No. 1 in October. Four months afterward, it returned to the summit as fans revisited his music in mourning. A later recording now led the songs that had first made them fans. Which Toby Keith song would you listen to first today?

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On February 13, 2024, just eight days after Toby Keith died at age 62, Billboard reported something that had never happened before on its Country Digital Song Sales chart. One…

Oldies Musics

Willie Nelson had written songs Nashville knew how to sell. Getting the industry to understand him as a singer proved harder. Patsy Cline made “Crazy” a classic. Faron Young took “Hello Walls” to No. 1, and Billy Walker found success with “Funny How Time Slips Away.” Willie’s own recordings seldom enjoyed comparable attention. His conversational phrasing and jazz-influenced timing resisted the polished approach RCA favored. Then, in 1970, his Tennessee home burned. His second marriage was also coming apart, and the losses helped loosen his ties to Nashville. He returned to Texas, where Austin’s emerging music scene offered possibilities he had struggled to find on Music Row. Rock audiences, honky-tonk crowds, and young songwriters were increasingly sharing venues. Willie found room to perform without fitting a conventional country image. Long hair, a beard, and worn denim gradually became familiar parts of his appearance, alongside songs delivered on his own terms. By 1973, a move to Atlantic Records had brought greater creative freedom. Arriving in New York to record *Shotgun Willie*, he found himself short of new material. The title track reportedly came together in a hotel bathroom, written on a sanitary-napkin envelope while he sat in his underwear. The sessions drew on country, blues, soul, and Texas musical traditions. The album did not immediately make him a major commercial star, but it established a direction that suited his voice rather than trying to reshape it. That summer, his first Fourth of July Picnic brought country performers and counterculture listeners together in Texas. The audience forming around him was becoming as distinctive as the records. Within a few years, Willie and Waylon Jennings would be central to what became known as outlaw country. The career that followed grew from decisions made during that uncertain transition: leaving Tennessee, finding an audience in Texas, and recording with the freedom to follow his instincts. The fire had taken his home. Starting again gave him a chance to reconsider where—and how—he wanted to make music.

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WILLIE NELSON’S HOUSE BURNED DOWN—AND GAVE HIM THE EXIT NASHVILLE NEVER COULD In 1970, Willie Nelson watched his Tennessee house burn and came away from the wreckage with something Nashville…

Country

When Eric Clapton wrote “Layla,” the woman he wanted was married to George Harrison, his close friend and musical collaborator. Clapton had played the celebrated lead guitar on Harrison’s “While My Guitar Gently Weeps.” As their friendship developed, his feelings for Pattie Boyd became increasingly consuming. She initially rejected him, and he channeled the longing into the music he was making with Derek and the Dominos. He later described that emotional turmoil as central to *Layla and Other Assorted Love Songs*. The title came from the Persian tale of Layla and Majnun, whose protagonist is overwhelmed by love for a woman he cannot have. Clapton recognized his own desperation in the story. The resulting song carried an unusually personal appeal. Behind its urgency was someone asking his friend’s wife to choose him. Yet Harrison’s friendship with Clapton survived. Pattie and George divorced in 1977, and she married Eric in 1979. George even attended their wedding celebration, remaining connected to both despite the painful history between them. Eric and Pattie’s marriage proved troubled, too. Infidelity and his personal difficulties contributed to its breakdown, and they divorced in 1988. By then, listeners had made “Layla” part of their own lives, far beyond the circumstances that inspired it. The song endured as the relationships changed: Pattie’s two marriages ended, while the friendship between the men who had loved her continued.

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ERIC CLAPTON WROTE “LAYLA” FOR THE WIFE OF ONE OF HIS CLOSEST FRIENDS Eric Clapton was already close enough to George Harrison to play the lead guitar on “While My…

Country

Robby Turner was adding steel guitar to “Belle of the Ball” when Waylon Jennings’s playing brought him to tears. His friend had been gone for ten years, but there he was on the recording. During Waylon’s final years, they had laid down songs with mostly voice, guitar, and Turner’s bass. Waylon died in 2002 before they could complete the arrangements. With Jessi Colter’s blessing, Turner invited musicians who had worked with Waylon to help finish the project. It became *Goin’ Down Rockin’: The Last Recordings*, released in 2012. Turner later told NPR about looking down at his instrument and seeing a tear fall as he heard Waylon play near the song’s end. Jessi, beside him for the interview, was hearing that memory for the first time. Their old studio rule, Turner explained, was to keep playing until Waylon smiled. Completing the recordings meant drawing on years of knowing what would earn that smile.

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Ten years after Waylon Jennings died, longtime friend and musician Robby Turner found himself looking down at his steel guitar, watching a tear fall onto the instrument. Turner was working…

Country

Rosanne Cash left a 1973 tour with her father carrying a handwritten list of a hundred songs—and memories of learning them directly from him. She was eighteen, newly graduated from high school, when she joined Johnny Cash on the road. Traveling through the South, he began mentioning older songs. Again and again, she admitted she didn’t know them. Her childhood in California had been filled mostly with rock and pop. Johnny realized how much of the music he treasured was unfamiliar to her and spent the afternoon assembling “100 Essential Country Songs.” “This is your education,” he told her. Rosanne saved the list. When she wanted to hear how a song went, her father could reach for his guitar and teach it to her. The time together mattered beyond the music. Her parents had divorced, and being on tour offered a closeness she had missed. “I wanted this. I wanted him,” she later said. In 2009, she recorded twelve selections for *The List*, returning to the songs her father had written down decades earlier. Have you listened to Rosanne Cash’s *The List*? Which song has stayed with you?

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In 1973, Johnny Cash discovered something surprising about Rosanne Cash. At 18 years old, the daughter of one of country music’s greatest legends barely knew some of the songs Johnny…

Country

Watching Carrie Underwood perform “You Ain’t Woman Enough” at the 2020 ACM Awards gave Loretta Lynn an idea for a recording of her own. Loretta and her daughter Patsy Lynn Russell had written “Still Woman Enough,” drawing inspiration from Loretta’s 2002 memoir. Patsy expected her mother to sing it alone. Loretta wanted company. She had already chosen Reba McEntire. After hearing Carrie include her old hit in a televised tribute to country music’s pioneering women, she wanted Carrie involved, too. Patsy later acknowledged that she hadn’t immediately grasped what her mother envisioned. Loretta heard an opportunity to bring women from different generations together around the song’s message. Reba and Carrie recorded their contributions at Cash Cabin Studio in late 2020. Their voices joined Loretta’s on the opening track of her fiftieth solo studio album, released in March 2021. Loretta’s explanation was characteristically direct: “We girl singers gotta stick together.” Have you heard their recording of “Still Woman Enough”? Which of these three singers has meant the most to you?

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In September 2020, Carrie Underwood stepped onto the Grand Ole Opry House stage during the Academy of Country Music Awards and performed a tribute to the women who helped build…

Country

Patty Loveless was enjoying some of her greatest professional success when illness and loss overwhelmed her family. In 1996, her mother and brother were both hospitalized. One of her sisters died. Her husband and longtime producer, Emory Gordy Jr., also became seriously ill. Patty tried to keep caring for everyone while meeting the demands of her career. Then she developed pneumonia. She later acknowledged that looking after others had left her neglecting her own health. Continuing to perform had become too much, but stopping carried fears of its own. *When Fallen Angels Fly* had won CMA Album of the Year, and a succession of hits had established her among country music’s leading female singers. After more than a decade of work, she worried that a year away might cost her the place she had earned. She took the time anyway. Loveless stepped back from touring to recover and be with her family. She later spoke openly about fearing the industry would move on without her. Even so, she waited until she felt physically and emotionally able to return. The break allowed her to keep working in the years that followed. At a point when awards and chart success suggested she should press ahead, her health required her to stop. For Patty, protecting her career meant accepting that she could not sustain it while giving every part of herself to everyone else.

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PATTY LOVELESS STEPPED AWAY AT THE PEAK OF HER CAREER TO SAVE THE LIFE BEHIND IT In 1996, Patty Loveless was collecting some of the biggest honors of her career…

Country

The Judds were still at the height of their success when Naomi’s health forced them to plan an ending. Just five weeks after the release of *Love Can Build a Bridge* in 1990, she announced that hepatitis C would prevent her from continuing to tour. She was in her mid-forties and later recalled that doctors could offer no assurance she would survive. Since their 1984 breakthrough, Naomi and Wynonna had earned more than a dozen No. 1 country hits and become a major concert attraction. Now they faced a farewell neither had expected to make so soon. They spent the following year taking their music back to audiences on an extended final tour. Each stop carried the knowledge that the mother and daughter might never perform together there again. On December 4, 1991, a Tennessee concert broadcast nationally on pay-per-view brought the tour to a close. The partnership that had helped lift them out of financial hardship was ending. Wynonna faced the uncertainty of continuing without her mother beside her. She later admitted she struggled to imagine who she was apart from The Judds. Naomi encouraged her to trust that she could succeed alone. A solo contract followed. By the time Wynonna’s debut arrived in 1992, advance orders had already surpassed those for the duo’s final album. Naomi’s illness had interrupted a career with momentum still behind it. For Wynonna, the next step meant learning how to carry that momentum herself—and discovering an identity beyond the name they had shared.

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Five weeks after The Judds released Love Can Build a Bridge in 1990, Naomi Judd stood before the public and announced that she was seriously ill.She had been diagnosed with…

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Country

The business card Alan Jackson kept in his billfold began with a conversation he wasn’t there to hear. His wife, Denise, was working as a flight attendant when she spotted Glen Campbell waiting for a flight at the Atlanta airport. Back in Georgia, Alan was still an unknown singer hoping to build a career in Nashville. Denise approached Glen and explained her husband’s ambition. Could he help? “Is he any good?” Glen asked, looking directly at her. She assured him Alan was both a good singer and a good songwriter. Glen handed her his card. That introduction eventually brought Alan to Glen’s Nashville publishing company, where he secured his first songwriting deal for $100 a week. Glen later joked that the modest paycheck was intentional: a few hard times would give the young writer something to write about. For years, Alan carried the card as a good-luck charm. He also understood how much depended on Denise having the nerve to start that conversation. Without her approaching Glen, he admitted, he might still have been driving a forklift.

Country

Kris Kristofferson could write for an audience of strangers. Writing a song for Johnny Cash—and singing it to him over dinner—frightened him. June Carter had made the request after Johnny returned from rehabilitation. She was inviting close friends, including Waylon Jennings and Jessi Colter, and wanted Kris to bring her husband something personal. Johnny had encouraged him during his difficult early Nashville years. Finding words for that friendship felt unusually exposing. Kris finished “Good Morning John” and performed it at the gathering, later recalling his embarrassment and guessing Johnny had felt much the same. An attempt to record it with Willie Nelson brought a different reaction. The supporting voices were meant to repeat Kris’s lines. When he sang, “I love you, John,” Willie replied, “He loves you, John.” Kris laughed so hard the recording fell apart. Waylon released his version in 1985. Kris waited until 2009 to include his own on an album, six years after Johnny’s death. The song began as June’s request for a dinner among friends. It endured as Kris’s way of thanking someone whose support had mattered long before he became successful. Have you heard his recording of “Good Morning John”?

Oldies Musics

Nine of the ten best-selling country songs belonged to Toby Keith on Billboard’s chart dated February 17, 2024. No artist had achieved that before. Following his death on February 5 at sixty-two, listeners returned to songs spanning his career. “Should’ve Been a Cowboy” ranked third, followed by “Courtesy of the Red, White and Blue” at fourth. “Beer for My Horses,” “American Soldier,” and “Red Solo Cup” also appeared in the Top 10. Luke Combs’s “Fast Car,” at No. 2, was the only interruption. Leading them all was “Don’t Let the Old Man In,” which sold 27,000 downloads during the tracking week. Toby wrote it after speaking with Clint Eastwood in 2018. Five years later, he performed it at the People’s Choice Country Awards while undergoing cancer treatment. That September 2023 appearance helped send it to No. 1 in October. Four months afterward, it returned to the summit as fans revisited his music in mourning. A later recording now led the songs that had first made them fans. Which Toby Keith song would you listen to first today?

Oldies Musics

Willie Nelson had written songs Nashville knew how to sell. Getting the industry to understand him as a singer proved harder. Patsy Cline made “Crazy” a classic. Faron Young took “Hello Walls” to No. 1, and Billy Walker found success with “Funny How Time Slips Away.” Willie’s own recordings seldom enjoyed comparable attention. His conversational phrasing and jazz-influenced timing resisted the polished approach RCA favored. Then, in 1970, his Tennessee home burned. His second marriage was also coming apart, and the losses helped loosen his ties to Nashville. He returned to Texas, where Austin’s emerging music scene offered possibilities he had struggled to find on Music Row. Rock audiences, honky-tonk crowds, and young songwriters were increasingly sharing venues. Willie found room to perform without fitting a conventional country image. Long hair, a beard, and worn denim gradually became familiar parts of his appearance, alongside songs delivered on his own terms. By 1973, a move to Atlantic Records had brought greater creative freedom. Arriving in New York to record *Shotgun Willie*, he found himself short of new material. The title track reportedly came together in a hotel bathroom, written on a sanitary-napkin envelope while he sat in his underwear. The sessions drew on country, blues, soul, and Texas musical traditions. The album did not immediately make him a major commercial star, but it established a direction that suited his voice rather than trying to reshape it. That summer, his first Fourth of July Picnic brought country performers and counterculture listeners together in Texas. The audience forming around him was becoming as distinctive as the records. Within a few years, Willie and Waylon Jennings would be central to what became known as outlaw country. The career that followed grew from decisions made during that uncertain transition: leaving Tennessee, finding an audience in Texas, and recording with the freedom to follow his instincts. The fire had taken his home. Starting again gave him a chance to reconsider where—and how—he wanted to make music.