The Greatest Oldies Music

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Terri Clark thought she was singing for John Anderson’s agent. She didn’t realize John himself would soon be listening. During her early Nashville years, Bobby Roberts invited her to his office for a meeting. With her guitar in hand, Terri launched into one of John’s hits, copying the distinctive voice she had admired since childhood. Bobby picked up the phone, called John, and let him hear the performance as it happened. John found it hilarious. The impression became a shared joke they returned to whenever they met. Terri had practiced that voice long before the office visit, singing for tips at Tootsie’s Orchid Lounge. Even after establishing her own career, she continued slipping impressions into her shows. In her tribute to John, she remembered the laughter as warmly as the music. She had grown up loving his voice; getting to make him laugh with her version became a memory worth keeping. “We’ll miss you, John,” she wrote. “Nobody’s gonna fill those shoes.”

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During the early days of Terri Clark’s Nashville career, a meeting in an agent’s office turned into a story that Terri Clark and John Anderson would remember whenever their paths…

Country

When Ben Haggard sang “Silver Wings” with an acoustic guitar in June 2016, he had been without his father for only two months. He posted the performance on YouTube on June 7. Merle had died April 6, his seventy-ninth birthday. Ben had spent much of his young life beside him, joining the Strangers as lead guitarist at fifteen. Now the son who had accompanied those familiar songs was carrying one in his own voice. Released in 1969, “Silver Wings” describes the helplessness of watching someone leave. Sung so soon after Merle’s death, its sense of separation carried an added sadness. Within two days, the video attracted more than 34,000 views. The choice also held another connection: the song had figured in Merle’s own carefully planned farewell. For listeners who had grown up with his records, Ben’s performance brought a familiar melody into a changed world. Merle was gone, but his son was still there to sing it.

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On June 7, 2016, Ben Haggard shared a video of an acoustic performance of “Silver Wings.” Two months earlier, on April 6, Merle Haggard had died on Merle Haggard’s 79th…

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Phil Balsley’s nickname, “The Quiet One,” suited his place onstage with the Statler Brothers. Away from the microphones, he carried responsibilities audiences rarely saw. His baritone sat between Don Reid’s lead, Harold Reid’s bass, and the tenor first sung by Lew DeWitt, then Jimmy Fortune. Harold delivered the jokes, Don often handled the talking, and Phil generally let his singing speak for him. But he also brought experience from an earlier job: keeping the books at his father’s sheet-metal business in Staunton, Virginia. An August 1985 newspaper profile, published before the group appeared at Michigan’s Berrien County Youth Fair, highlighted that less familiar contribution. It identified Phil as the member who routinely looked after the Statlers’ business and administrative affairs. Alongside the rehearsals and performances, there were practical matters to track—and Phil helped keep them in order. His voice was easy to recognize in those four-part harmonies. The work he did to support the group’s career was considerably quieter, but it belonged to his contribution just as surely as the baritone.

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They called Phil Balsley “The Quiet One.” But a newspaper published in August 1985 revealed something many fans may never have realized: Phil Balsley was doing much more than singing…

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When Loretta Lynn was asked which song she wished had received its own single release, she remembered an afternoon on Patsy Cline’s front steps. Patsy had died two months earlier, aged thirty, in the March 5, 1963, plane crash near Camden, Tennessee. Their friendship had lasted less than two years, but Loretta would describe her as the big sister she had never had. Sitting outside the house, Loretta looked up and spoke a short sentence. It supplied the title of a song she wrote within minutes. Listeners could hear it as a woman mourning a lost romance in a once-shared home. Nothing in the lyrics named Patsy. Loretta, however, made its inspiration clear: she had written it about her friend. Decca released it in 1964 beneath an upbeat honky-tonk A-side that reached No. 3. The song Loretta cherished remained on the flip side, never promoted on its own. She explained the decision in the language of the time: “unless you had some little up-tempo thang you didn’t make it.”

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The song is “This Haunted House.” Loretta Lynn wrote it about two months after Patsy Cline died, sitting on the steps of her late friend’s home, and she finished it…

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For more than twenty years, a song Johnny Cash wanted Porter Wagoner to hear waited inside an envelope Marty Stuart had forgotten to deliver. In the early 1980s, Stuart was touring with Cash when they started listening to Wagoner’s records. Cash had a song in mind for him and entrusted Stuart with a cassette to pass along. Once they returned home, the errand slipped his mind. It resurfaced when Stuart began selecting songs for Wagoner’s *Wagonmaster*. He remembered the tape, tracked it down, and finally brought the song to Wagoner in the summer of 2006. By then, Cash had been dead for nearly three years. Wagoner recorded it for the album released in June 2007. It would be his last. He died that October, aged eighty. Cash never heard the finished performance. But the cassette eventually fulfilled its purpose: the singer he had chosen finally gave the song his voice. Can you name the song that took more than two decades to reach Porter Wagoner?

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Johnny Cash gave Marty Stuart a simple assignment: deliver a song to Porter Wagoner. More than twenty years passed before Marty Stuart finished the job. By then, Johnny Cash was…

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Before John Carter Cash produced Loretta Lynn’s final four studio albums, she had looked after him backstage while his mother performed. Born in 1970 to Johnny Cash and June Carter Cash, John spent his childhood around musicians who would remain part of his life. When Loretta appeared on Johnny’s touring shows, June sometimes left him in her care before taking the stage. “Take care of Johnny,” she would say. Years later, their connection brought Loretta to Cash Cabin, the Hendersonville, Tennessee, studio Johnny had built on his property. Beginning in 2007, John Carter and Loretta’s daughter, Patsy Lynn Russell, produced sessions that eventually yielded more than ninety recordings. Loretta was seventy-five when they started. Among the songs were mountain tunes her mother had taught her long before Nashville, back in Butcher Hollow. *Full Circle* arrived in 2016, when she was eighty-three, and became her highest-charting album on the Billboard 200. Three more studio albums followed from the sessions, concluding in 2021. Loretta appreciated the turn their lives had taken. The child she once watched while June sang was now helping preserve her own voice. “So now he’s recording me,” she said.

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In the early 1970s, when Loretta Lynn shared the road with Johnny Cash, there was a small job that came with the tour. While June Carter Cash sang, somebody had…

Country

When Dolly Parton and Kenny Rogers sang “I Will Always Love You” at Dollywood’s twenty-fifth-anniversary celebration in 2010, the song offered a fitting expression of their friendship. Dolly had written it in 1973 as a farewell to Porter Wagoner, conveying affection and gratitude as she prepared to leave their professional partnership. Singing it with Kenny gave those familiar words another personal setting. Her clear, rising voice met his warm, weathered delivery, bringing tenderness to a performance shaped by years of shared music and easy understanding. Amid the anniversary festivities, the duet became a quiet acknowledgment of what they meant to each other. Its appeal rested in that familiarity: two longtime friends singing words of appreciation that needed little explanation.

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A breathtaking portrait of a legendary kinship, where the world’s most famous farewell song becomes a tender, living tribute to a lifelong bond. In 2010, during the milestone television special…

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Billy Joe Shaver’s last reported performance took place in his kitchen. He sang “Live Forever,” the song he had written with his late son, Eddy. In April 2020, with the pandemic keeping musicians home, longtime guitarist Jeremy Lynn Woodall visited to record Billy Joe for a local radio station. There was no audience or stage lighting—just a familiar song in the room where he lived. Eddy had brought him the melody years earlier. Billy Joe worked for months on the lyrics before father and son finished it together. After Eddy died on New Year’s Eve in 2000, the song remained in his father’s repertoire. Billy Joe died on October 28, 2020, aged eighty-one. In 2022, Willie Nelson and Lucinda Williams recorded “Live Forever” together for a tribute album that also included George Strait, Miranda Lambert, and Steve Earle. By then, neither of its writers was alive to hear it. But a song they had built together was finding its way into other voices, carrying their partnership beyond that final kitchen performance.

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In April 2020, Billy Joe Shaver gave what would become his final widely reported performance. There was no concert hall, no cheering audience, and no stage waiting for one of…

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Toby Keith’s support for American troops began with the Army veteran who raised him. His father taught him to respect the flag and the people who served beneath it. After his father’s death in 2001 and the September 11 attacks, Toby wrote “Courtesy of the Red, White and Blue” in roughly twenty minutes. Its anger drew strong criticism, but he defended the song. In 2006, he put that conviction plainly: “If you believe in it enough, it’s worth fightin’ for.” “American Soldier” expressed another side of his respect, focusing on service members balancing duty with the families they had to leave behind. His commitment also took him overseas. Beginning in 2002, Toby joined USO tours, performing at military bases and remote outposts in dangerous war zones. By 2014, he had entertained more than 250,000 service members across seventeen countries. Toby never served in uniform. He found his own way to contribute: making the trips, spending time with troops, and bringing music to places far from home. The support he sang about became a recurring commitment on his calendar.

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“If you believe in it enough, it’s worth fightin’ for.” — Toby Keith, 2006 When Toby Keith spoke those words during a CBS News interview in September 2006, they weren’t…

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Kris Kristofferson hadn’t expected to find his songwriting in *Taxi Driver*. Then he saw Robert De Niro holding his album and heard a familiar description: “a walking contradiction.” The song had appeared five years earlier on Kris’s 1971 album, *The Silver Tongued Devil and I*. Its complicated central figure drew on men he knew well, including Johnny Cash, Chris Gantry, Ramblin’ Jack Elliott, and Dennis Hopper. Later, Kris acknowledged how much of himself he had put into that character, too. In the 1976 film, Betsy, played by Cybill Shepherd, gives Travis Bickle the record and uses the song’s words to describe him. A character Kris had assembled from friends—and his own contradictions—had found an unexpected place in Scorsese’s story. Recalling the scene in a 1999 interview, Kris spoke warmly about seeing his album and hearing his words onscreen. He regarded the inclusion as one of the kindest things Martin Scorsese had done for him. Can you name the Kris Kristofferson song Betsy quoted in *Taxi Driver*?

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In 1976, audiences watching Martin Scorsese’s Taxi Driver heard an unexpected name: Kris Kristofferson. During a conversation with Travis Bickle, played by Robert De Niro, Betsy, played by Cybill Shepherd,…

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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.

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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.”