The Greatest Oldies Music

Country

Before Toby Keith was known for the songs that got a whole bar singing, he could break your heart with a ballad like “Wish I Didn’t Know Now.” It came out in February 1994 and reached No. 2 on Billboard’s country chart. The melody is simple, and Toby gives the words room to hurt. What’s always stayed with me is how familiar that regret sounds. You think finding out the truth will make it easier to move on. Then you find yourself looking back at a memory that used to make you happy, and even that feels different now.

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Released in 1994 as the final single from his self-titled debut album, this track cemented Keith’s status as a rising star within the country music scene. But what truly elevates…

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Dolly Parton ended her tribute to Toby Keith by singing a few words without accompaniment. Anyone who knew “I Will Always Love You” would have recognized the melody. When Toby died on February 5, 2024, Dolly wrote that it was always hard to lose one of country music’s brothers and sisters. She called him one of the greats in every way and said he’d be missed, even as his music and legacy lived on. That summer, Carrie Underwood, Eric Church, Jelly Roll, Luke Bryan and Lainey Wilson were among the artists who gathered at Nashville’s Bridgestone Arena for *Toby Keith: American Icon*. The concert was taped on July 29, and NBC aired the two-hour special on August 28. Dolly sent a video message. She spoke about her friend, then looked into the camera and told him they would always love him. As she reached the last few words, she let them fall into the melody of her own song. There was no band behind her. Just Dolly, singing goodbye to Toby.

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Backgroud When Toby Keith died on February 5, 2024, after battling stomach cancer, the country music world lost one of its most recognizable voices. Dolly Parton was among the artists…

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Doctors at the University of Virginia didn’t expect Jimmy Fortune’s newborn son to live two hours. Jimmy Jr. lived 51 years. He was born with spina bifida in Charlottesville in January 1973. His father was seventeen. Fortune later said it was the most severe case the hospital had seen and that his son had been “to hell and back.” When Fortune joined the Statler Brothers as their new tenor in 1982, he’d never written a song. At a concert in 2018, he told the audience how one of his songs came about. Jimmy Jr. was in the hospital for surgery, and his father was on the road with no way to get home. So he put what he was feeling down on paper. The song reached No. 1 on November 30, 1985. It was the last No. 1 the Statler Brothers ever had. Jimmy Jr. died on October 15, 2024, after what his father described as a sudden bout of pneumonia. When Fortune shared the news, he called his son his inspiration. He still sings the song.

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The song is “Too Much on My Heart.” Jimmy Fortune wrote it, the Statler Brothers took it to No. 1 on Billboard’s country chart on November 30, 1985, and no…

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Alan Jackson wrote a song to sing at a funeral. Two years later, people were hearing it on country radio. Leslie Fitzgerald, known to the Jackson family as Sissy, worked in their home and was part of their everyday lives. When she died in a motorcycle accident in May 2007, Alan wrote a song for her and sang it at her funeral. He later remembered her family telling him how much it had helped them through the loss. Alan also recorded it with his longtime producer, Keith Stegall. They kept the arrangement simple: Alan’s voice, a guitar and harmony vocals. When people at his label heard the recording, they asked him to put it on his next album. It appeared on *Good Time* in 2008. The following year, it came out as a single and reached No. 9 on Billboard’s country chart. A song Alan had written for one family was now reaching people who had never known Sissy. Do you remember which Alan Jackson song it was?

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In 2009, Alan Jackson released one of the most personal songs of an already remarkable career. It wasn’t written for a chart position, a new album, or a concert audience.…

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For six seasons of *The Dukes of Hazzard*, viewers heard Waylon Jennings every week. In the opening credits, they saw him strum a guitar, but the camera stopped at his collar. Waylon was the Balladeer, the dry voice that let you know Bo and Luke were in trouble again, sometimes with the General Lee frozen in midair. He also wrote and sang the theme that opened and closed the show. When he recorded it as a single in 1980, he slipped in a joke about his mother wondering why television kept showing his hands when it could show his face. The record went to No. 1 on Billboard’s country chart. Then came the final season. On Friday, September 28, 1984, CBS aired “Welcome, Waylon Jennings.” Waylon played himself, an old friend of Uncle Jesse’s who brought his traveling country music museum to Hazzard County. It was the only episode in which viewers got to see his face. Before the hour was over, he was up onstage at the Boar’s Nest, strumming a guitar just as he’d done in the opening credits for years. This time, the camera went all the way up. Do you remember the name of the theme song?

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On Friday nights from 1979 to 1985, Waylon Jennings was part of The Dukes of Hazzard from the first note to the last. He sang the theme, “Good Ol’ Boys,”…

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By 2019, Kris Kristofferson could sing an entire concert and barely remember it the next morning. His guitarist, Scott Joss, said Kris would walk out, play the songs and smile at the crowd, and “it’s like nothing’s wrong.” His memory had started slipping in his seventies. “I can remember my songs, so I can perform,” he said at 77. “But other than that…” He even began writing a song about losing his memory. Then he forgot that one, too. For years, doctors suspected Alzheimer’s or the effects of old blows to the head. In 2016, he tested positive for Lyme disease. His wife, Lisa, remembered the change after he stopped taking the Alzheimer’s medication and received Lyme treatment: “All of a sudden he was back.” His short-term memory never fully recovered. In 1965, Kris had turned down a job teaching English at West Point and ended up sweeping floors at a Nashville recording studio. His parents all but disowned him. He later called the experience liberating. He played his last full concert aboard a cruise ship on January 30, 2020. “Me and Bobby McGee” was still on the set list.

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In the summer of 2019, Kris Kristofferson was about to turn 83 and still touring, this time with a small band behind him. His guitarist, Scott Joss, who had once…

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More than twenty years after Waylon Jennings died, Shooter Jennings found enough unheard recordings by his father to fill three albums. They were full-band performances Waylon had cut with the Waylors between tours in the 1970s and early ’80s, with Richie Albright on drums and Ralph Mooney on steel guitar. Shooter remembered the tapes from the house where he grew up. One room was always locked. Inside were gray boxes with notes written in marker. He knew they held his dad’s work. The tapes had been digitized in 2008. When Shooter started sorting through them at Sunset Sound in Hollywood in 2024, the files had no song titles. He had hundreds of sessions to listen through. In those recordings, he heard the father he remembered, a man he called “a gentle guy.” Shooter brought in surviving members of the Waylors to fill in missing parts and mixed the recordings on a console from 1976. The first album, *Songbird*, came out in October 2025. The second, *Diamonds*, is due November 13. Shooter found the title track in pieces across three sessions. Only after he heard it all together did he realize who’d dropped by the studio one December night in 1978 and picked up a guitar: Glen Campbell.

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Waylon Jennings died in February 2002 at 64. More than two decades later, his son Shooter Jennings went looking through his father’s personal recordings expecting to find a song or…

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Janet Robbins found out at her father’s funeral that he’d listened to the cassette she sent him. A friend told her Marty had played it for him. Janet had moved to California, where she recorded a few songs, including one she’d written herself. She mailed the tape to her dad in Tennessee. He never mentioned it to her. Marty had always kept his wife and daughter apart from his life onstage. Janet was nineteen the first time she saw him perform. When it came to her own future, he’d told her she could do whatever she wanted, as long as she stayed out of the music business. Marty died in December 1982 at fifty-seven. Janet was about twenty-three. Years later, she told biographer Diane Diekman what the friend had said at the funeral: Marty thought his daughter was so talented that he didn’t know how to tell her.

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Janet Robbins never knew whether her father had listened to the songs she mailed him. Marty Robbins never brought it up. It was only on the day of his funeral…

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Minnie Pearl tried to lift Hank Williams’s spirits by singing one of his own songs, “I Saw the Light.” For a little while, he sang with her. Hank had already played one show that day, and the promoter was worried he might not make it through the next one. Minnie was asked to stay with him between performances. She and the promoter’s wife took him for a drive, hoping it might do him some good. Somewhere along the way, Minnie started singing the gospel song Hank had written. He joined in. Years later, she could still remember the sound of his voice cracking and drifting off-key before he stopped singing altogether. Hank looked at her and put his hand on hers. The song had brought comfort to people who’d never met him. In the car that day, Minnie remembered, he told her what he was feeling: “That’s just it, Minnie. There ain’t no light. It’s all dark.”

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Hank Williams wrote “I Saw the Light,” one of the most beloved gospel songs in country music. But during a difficult moment on the road, when Minnie Pearl tried to…

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Johnny Cash and June Carter won their first Grammy together for singing about a marriage that had lost its spark. The next day, they got married. In their 1967 duet, Johnny plays a husband who talks about leaving town. June plays the wife who’s heard enough of that talk and practically dares him to go. The two sound like they’ve had this argument before, and the fun is in hearing how quickly June comes back at him. The record reached No. 2 on Billboard’s country chart. On February 29, 1968, the duet won Best Country & Western Performance by a Duet or Group. On March 1, Johnny and June exchanged vows at First United Methodist Church in Franklin, Kentucky. The couple on the record could barely stand each other by the time the song was over. The two singers who’d made the bickering sound so good were just getting started. Do you remember which song earned Johnny and June a Grammy the day before their wedding?

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On February 29, 1968, Johnny Cash and June Carter received one of country music’s highest honors for a song about a married couple whose romance had lost its spark. Just…

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You Missed

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Before Toby Keith was known for the songs that got a whole bar singing, he could break your heart with a ballad like “Wish I Didn’t Know Now.” It came out in February 1994 and reached No. 2 on Billboard’s country chart. The melody is simple, and Toby gives the words room to hurt. What’s always stayed with me is how familiar that regret sounds. You think finding out the truth will make it easier to move on. Then you find yourself looking back at a memory that used to make you happy, and even that feels different now.

Country

Dolly Parton ended her tribute to Toby Keith by singing a few words without accompaniment. Anyone who knew “I Will Always Love You” would have recognized the melody. When Toby died on February 5, 2024, Dolly wrote that it was always hard to lose one of country music’s brothers and sisters. She called him one of the greats in every way and said he’d be missed, even as his music and legacy lived on. That summer, Carrie Underwood, Eric Church, Jelly Roll, Luke Bryan and Lainey Wilson were among the artists who gathered at Nashville’s Bridgestone Arena for *Toby Keith: American Icon*. The concert was taped on July 29, and NBC aired the two-hour special on August 28. Dolly sent a video message. She spoke about her friend, then looked into the camera and told him they would always love him. As she reached the last few words, she let them fall into the melody of her own song. There was no band behind her. Just Dolly, singing goodbye to Toby.

Country

Doctors at the University of Virginia didn’t expect Jimmy Fortune’s newborn son to live two hours. Jimmy Jr. lived 51 years. He was born with spina bifida in Charlottesville in January 1973. His father was seventeen. Fortune later said it was the most severe case the hospital had seen and that his son had been “to hell and back.” When Fortune joined the Statler Brothers as their new tenor in 1982, he’d never written a song. At a concert in 2018, he told the audience how one of his songs came about. Jimmy Jr. was in the hospital for surgery, and his father was on the road with no way to get home. So he put what he was feeling down on paper. The song reached No. 1 on November 30, 1985. It was the last No. 1 the Statler Brothers ever had. Jimmy Jr. died on October 15, 2024, after what his father described as a sudden bout of pneumonia. When Fortune shared the news, he called his son his inspiration. He still sings the song.

Country

Alan Jackson wrote a song to sing at a funeral. Two years later, people were hearing it on country radio. Leslie Fitzgerald, known to the Jackson family as Sissy, worked in their home and was part of their everyday lives. When she died in a motorcycle accident in May 2007, Alan wrote a song for her and sang it at her funeral. He later remembered her family telling him how much it had helped them through the loss. Alan also recorded it with his longtime producer, Keith Stegall. They kept the arrangement simple: Alan’s voice, a guitar and harmony vocals. When people at his label heard the recording, they asked him to put it on his next album. It appeared on *Good Time* in 2008. The following year, it came out as a single and reached No. 9 on Billboard’s country chart. A song Alan had written for one family was now reaching people who had never known Sissy. Do you remember which Alan Jackson song it was?