The Greatest Oldies Music

Country

Some of Toby Keith’s most affecting performances sit outside his biggest hits. “When Love Fades,” co-written with Chuck Cannon and released in 1999, peaked at No. 44 on Billboard’s country chart. I’ve always appreciated how gently he handles its heartbreak. The sadness comes from recognizing distance where there used to be certainty, as two people struggle with feelings that have changed. His delivery gives that uncertainty room, revealing the tenderness listeners could sometimes overlook beneath his swagger. It’s a song I hear differently with age. Experience makes its quiet sorrow more familiar—the realization that love can change before either person knows quite how to say it.

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Released in 1999 as the lead single for his album How Do You Like Me Now?!, this song marked a significant moment in Keith’s career. It wasn’t just another country…

Country

“I Still Miss Someone” became a daughter’s tribute at the Ryman on November 10, 2003. Beneath a large portrait of Johnny Cash, Rosanne sang the evening’s first song from her father’s catalog. He had been gone nearly two months. More than 2,000 people filled the old church pews, and one of his early guitars rested onstage. A Telecaster and upright bass accompanied her. Johnny had written the song with his nephew, Roy Cash Jr., and recorded it as a B-side in 1958. Rosanne was three then. Forty-five years later, she was singing his words back into a room gathered to remember him. She took it slowly. A critic attending the service wrote that her performance expressed much of what the audience felt. The title needed little explanation that night. Later, family photographs appeared on a screen while a duet Rosanne and Johnny had released that spring played beneath them—a song confronting the possibility of losing a parent. The closing brought the Cash family together onstage. They sang “We’ll Meet Again,” and the audience joined them. Rosanne had opened with the ache of someone missing. At the end, the family gave everyone a song they could sing together.

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On the night of November 10, 2003, more than 2,000 people filled the pews of the Ryman Auditorium in Nashville for the Johnny Cash Memorial Tribute. Tickets were free and…

Country

Major Pete Cruz waited offstage while his wife cried through “American Soldier.” She believed he was still in Afghanistan. Toby Keith knew he was only moments away. At a Houston concert in September 2012, Toby asked whether anyone had a loved one serving overseas. Hands rose throughout the crowd. He invited Cruz’s wife up and dedicated the song to her husband. She tried to sing along, unaware that the evening had been arranged around a surprise. Before the show, Toby’s crew had told him the major was coming home early. His invitation had been deliberate. Near the song’s end, the guitar shifted into the national anthem. Cruz stepped onto the stage carrying Toby’s red, white and blue guitar. His wife turned and recognized the man she had been missing. “Welcome home, Major Cruz,” Toby said. “Thank you for your service.” He kept them beside him for “Courtesy of the Red, White and Blue,” letting the reunion continue in front of the cheering crowd. Toby’s connection with military families extended well beyond that concert. Beginning in 2002, his overseas performances reached more than 250,000 troops across seventeen countries, including Iraq and Afghanistan. But that night, the meaning of coming home was right there beside him: a woman embracing the husband she hadn’t expected to see.

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On September 8, 2012, Toby Keith was in the middle of a show in Houston, Texas, when a man in uniform walked out from the side of the stage with…

Country

Lionel Richie had a melody, a verse and a working title: “Baby.” Kenny Rogers’s enthusiasm for his wife helped change that last part. In a Las Vegas dressing room in 1980, Richie sat at an out-of-tune piano, ready to play. Kenny wanted to tell him something first. “Before you do your song, let me tell you,” Richie recalled him saying. “I married a lady, a real lady.” He was talking about Marianne Gordon, the Georgia-born *Hee Haw* actress he had married three years earlier. Kenny praised her taste, class and style, then asked the name of Richie’s song. “Lady,” Richie answered. “I’m no fool,” he later joked. That fall, Kenny’s recording reached No. 1 on the country chart and spent six consecutive weeks atop the Billboard Hot 100. A conversation about Marianne had helped give one of his biggest records its name. Their marriage ended in 1993. Asked about a settlement reportedly worth around $60 million, Kenny said, “She deserves every penny.” After his death in 2020, Marianne remembered their years together with affection. There had been many fabulous memories, she said. “I like to think about those.” “Lady” remained among the songs listeners loved most—a lasting reminder of how warmly Kenny had spoken about her that day.

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In the fall of 1980, Kenny Rogers’ “Lady” climbed to No. 1 on the Billboard Hot 100 on November 15 and stayed there for six weeks. It also topped the…

Country

Waylon Jennings still had shows booked when doctors amputated his left foot in December 2001. He expected a prosthetic would help him walk again—and hoped to return to touring within months. Diabetes had made walking difficult for more than two years. At 64, the singer who had survived the loss of Buddy Holly and helped reshape country music with Willie Nelson was facing increasingly serious limits. He had already acknowledged them onstage. During his January 2000 performances at Nashville’s Ryman Auditorium, Waylon sang from a chair. “I guess y’all noticed I’m sittin’ on this chair,” he told the audience. “…but I’m gettin’ around.” He opened with “Never Say Die,” a song he had written himself. In October 2001, the Country Music Hall of Fame honored him. Waylon said he had once been told he would never get in. He stayed away from the ceremony, sending his son Buddy to accept on his behalf. Even after surgery at a Phoenix hospital, he was looking toward another return. It never came. On February 13, 2002, he died in his sleep at his Arizona home. “Waylon was my life,” Jessi Colter said after nearly thirty-three years of marriage. “He was my whole world.” Around his Hall of Fame induction, Waylon had offered his own measure of a career: “I think you need to play your music and do the best you can with that, and that’s what you’ll be remembered for.” What’s the first Waylon Jennings song you remember hearing?

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In December 2001, doctors at a Phoenix hospital amputated Waylon Jennings’ left foot. Diabetes had been wearing him down for years, and an infection had finally made the decision for…

Country

“Play solo, Glen,” the screen at his feet instructed. Sometimes Glen Campbell read the words aloud. Then he played, his hands finding what his memory could no longer reliably supply. After announcing his Alzheimer’s diagnosis in 2011, Glen took his music on a farewell tour. His children performed beside him, a teleprompter supplied lyrics, and audiences helped by singing along. There were difficult moments, but the guitar playing remained remarkable. This was the musician who had contributed to the Beach Boys’ *Pet Sounds*, now navigating a familiar stage with unfamiliar obstacles. In January 2013, he entered a Los Angeles studio for his final recording sessions. “I’m Not Gonna Miss You” came together in small pieces—sometimes a line, sometimes a single word. The recording earned a Grammy and an Oscar nomination. Later, he kept two guitars in his room. Visiting Nashville friends would play, then pass an instrument to him. He would still attempt a little picking. Glen died on August 8, 2017, at 81, surrounded by family. His life had begun among twelve children in an Arkansas sharecropping family, without electricity or running water. That childhood eventually gave way to studios, concert halls, “Wichita Lineman” and “Rhinestone Cowboy.” Toward the end, a guitar still offered him something familiar to reach for. What’s the first Glen Campbell song you remember hearing?

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In June 2011, Glen Campbell told the world he had Alzheimer’s disease. He was 75. Most people expected him to step quietly out of sight. Instead, he and his family…

Country

For two hours, nobody applauded. Then Willie Nelson closed a September 2001 telethon with “America the Beautiful,” and the silence finally broke. Ten days after 9/11, nearly 60 million viewers watched performers on candlelit stages in New York, Los Angeles and London. There were no commercials or formal introductions. Between performances, familiar faces asked people to call and donate. Clint Eastwood introduced the closing moment by saying those who wanted 300 million victims would get 300 million heroes instead. Willie, 68, began singing with his guitar. Behind him, actors and musicians joined in: Tom Cruise, Julia Roberts, Robin Williams and Reba McEntire, who had been answering pledge calls. Stevie Wonder added harmonica. The gathering had a loose, uncertain quality. One critic described it as shabby and apparently unrehearsed, suggesting Willie took everyone through more repetitions than expected. That looseness gave the finale its warmth. People who had spent the evening performing, speaking or answering phones were now singing together. At the end, the participants clapped and cheered. After an entire broadcast without applause, their voices and hands supplied the night’s final sound.

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On the night of September 21, 2001, ten days after the attacks, nearly 60 million viewers tuned in to America: A Tribute to Heroes. The two-hour benefit ran without commercials…

Country

The pie Oliver “Doolittle” Lynn bought at a Kentucky auction came with a surprise: Loretta Webb had put salt in it instead of sugar. He married its young baker anyway. Their wedding was January 10, 1948. Loretta was fifteen; Doo was twenty-one. Before she turned twenty-one, they had four children. Later, he bought her a $17 Harmony guitar, convinced she could sing as well as anyone they heard on the radio. Getting a record made was only the beginning. Her 1960 debut, “I’m a Honky Tonk Girl,” came from a small label without the resources for a national promotional campaign. Loretta and Doo mailed records and photographs to radio stations, then packed the car and went looking for listeners themselves. Doo drove. Loretta walked into stations, introduced herself and asked disc jockeys to give her song a chance. Their budget meant nights sleeping in the car and meals of baloney-and-cheese sandwiches on park benches. Afterward, they headed for another town and another radio station. The record eventually reached No. 14 on Billboard’s country chart. An invitation to the Grand Ole Opry followed. Before her October 15, 1960, debut, they spent another night in the car. Loretta woke to discover that Doo had parked outside the very building she had dreamed of entering. Her nerves left her with little memory of the performance. The life they built together held far more difficulty than that early journey might suggest. Loretta spoke plainly about their marriage, and her songs gave some of its hardest experiences an audience. They remained married until Doo died in 1996, nearly forty-eight years after their wedding. Away from touring, she returned to Hurricane Mills, where she cooked and preserved vegetables from her garden. That home life continued alongside a career that had begun with a cheap guitar and two people carrying records from station to station. Before Nashville knew her name, Loretta had already learned how to walk through a door and ask to be heard.

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On the morning of October 15, 1960, Loretta Lynn woke up in the front seat of an old Mercury sedan and realized her husband, Oliver “Doolittle” Lynn, had parked it…

Country

Merle Haggard told his family he would die on his birthday. About a week later, on April 6, 2016, he turned 79 and died at his Northern California home, surrounded by loved ones. Pneumonia had forced repeated cancellations over the preceding months. Still, he performed in Las Vegas that February, with Toby Keith helping him finish the show. His appearance at Oakland’s Paramount Theatre soon afterward became his final public concert. Most listeners had no reason to think they were hearing him for the last time. Only a year earlier, Merle and Willie Nelson had released *Django and Jimmie*. It reached No. 1 on the country albums chart and included “Missing Ol’ Johnny Cash,” a title with particular meaning for Merle. Decades before, he had watched Cash perform from the prisoners’ seats at San Quentin. Merle was serving time, still years away from the records that would make his name. He later credited that encounter with helping him become a better man. The years afterward brought “Mama Tried,” a pardon signed by Ronald Reagan and induction into the Country Music Hall of Fame. Eventually, the former inmate was making records with Willie Nelson and remembering Cash in song. His final birthday closed a life whose direction had once looked very different. Fans were left with decades of recordings—and memories of where those songs first found them. What’s the first Merle Haggard song you remember hearing?

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On April 6, 2016, Merle Haggard turned 79. That same morning, he died of complications from pneumonia at his home in Northern California, with family and friends around him. What…

Oldies Musics

Christmas morning brought Willie Nelson devastating news in 1991. His son Billy had been found dead in Tennessee at 33. Police described his death as suicide. Willie was already facing severe financial trouble, but losing his eldest son changed the weight of those worries. Billy had struggled with alcohol and personal difficulties. Afterward, Willie spoke about the guilt he felt and the years touring had taken him away from his children. He knew he had not always been the father he wanted to be. Looking back meant confronting those absences, while also recognizing that blaming himself endlessly could neither explain everything nor bring Billy home. Much of the family’s grief remained private. Willie shared little about the circumstances, and his sister Bobbie later described an understanding between them that needed few words. Each knew the sorrow the other carried. Billy’s siblings also remembered the depth of their father’s pain. Willie had endured financial crises, failed marriages and the destruction of a home by fire. Those experiences had involved decisions to make and practical ways to begin again. There was no comparable solution to losing his son. Life continued, with family, travel and music still part of it, but Billy’s absence continued too. Willie had to find a way to live with that loss without allowing regret to consume all the years that remained.

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WILLIE NELSON LOST HIS SON BILLY ON CHRISTMAS DAY—AND FACED A GRIEF HE COULD NOT FIX On Christmas morning in 1991, Willie Nelson received the kind of call no father…

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Country

Some of Toby Keith’s most affecting performances sit outside his biggest hits. “When Love Fades,” co-written with Chuck Cannon and released in 1999, peaked at No. 44 on Billboard’s country chart. I’ve always appreciated how gently he handles its heartbreak. The sadness comes from recognizing distance where there used to be certainty, as two people struggle with feelings that have changed. His delivery gives that uncertainty room, revealing the tenderness listeners could sometimes overlook beneath his swagger. It’s a song I hear differently with age. Experience makes its quiet sorrow more familiar—the realization that love can change before either person knows quite how to say it.

Country

“I Still Miss Someone” became a daughter’s tribute at the Ryman on November 10, 2003. Beneath a large portrait of Johnny Cash, Rosanne sang the evening’s first song from her father’s catalog. He had been gone nearly two months. More than 2,000 people filled the old church pews, and one of his early guitars rested onstage. A Telecaster and upright bass accompanied her. Johnny had written the song with his nephew, Roy Cash Jr., and recorded it as a B-side in 1958. Rosanne was three then. Forty-five years later, she was singing his words back into a room gathered to remember him. She took it slowly. A critic attending the service wrote that her performance expressed much of what the audience felt. The title needed little explanation that night. Later, family photographs appeared on a screen while a duet Rosanne and Johnny had released that spring played beneath them—a song confronting the possibility of losing a parent. The closing brought the Cash family together onstage. They sang “We’ll Meet Again,” and the audience joined them. Rosanne had opened with the ache of someone missing. At the end, the family gave everyone a song they could sing together.

Country

Major Pete Cruz waited offstage while his wife cried through “American Soldier.” She believed he was still in Afghanistan. Toby Keith knew he was only moments away. At a Houston concert in September 2012, Toby asked whether anyone had a loved one serving overseas. Hands rose throughout the crowd. He invited Cruz’s wife up and dedicated the song to her husband. She tried to sing along, unaware that the evening had been arranged around a surprise. Before the show, Toby’s crew had told him the major was coming home early. His invitation had been deliberate. Near the song’s end, the guitar shifted into the national anthem. Cruz stepped onto the stage carrying Toby’s red, white and blue guitar. His wife turned and recognized the man she had been missing. “Welcome home, Major Cruz,” Toby said. “Thank you for your service.” He kept them beside him for “Courtesy of the Red, White and Blue,” letting the reunion continue in front of the cheering crowd. Toby’s connection with military families extended well beyond that concert. Beginning in 2002, his overseas performances reached more than 250,000 troops across seventeen countries, including Iraq and Afghanistan. But that night, the meaning of coming home was right there beside him: a woman embracing the husband she hadn’t expected to see.

Country

Lionel Richie had a melody, a verse and a working title: “Baby.” Kenny Rogers’s enthusiasm for his wife helped change that last part. In a Las Vegas dressing room in 1980, Richie sat at an out-of-tune piano, ready to play. Kenny wanted to tell him something first. “Before you do your song, let me tell you,” Richie recalled him saying. “I married a lady, a real lady.” He was talking about Marianne Gordon, the Georgia-born *Hee Haw* actress he had married three years earlier. Kenny praised her taste, class and style, then asked the name of Richie’s song. “Lady,” Richie answered. “I’m no fool,” he later joked. That fall, Kenny’s recording reached No. 1 on the country chart and spent six consecutive weeks atop the Billboard Hot 100. A conversation about Marianne had helped give one of his biggest records its name. Their marriage ended in 1993. Asked about a settlement reportedly worth around $60 million, Kenny said, “She deserves every penny.” After his death in 2020, Marianne remembered their years together with affection. There had been many fabulous memories, she said. “I like to think about those.” “Lady” remained among the songs listeners loved most—a lasting reminder of how warmly Kenny had spoken about her that day.