The Greatest Oldies Music

Country

“WE KNEW THEY WERE IN LOVE BEFORE THEY KNEW THEY WERE IN LOVE.” — KIMBERLY SCHLAPMAN, ABOUT HER TWO BANDMATES WHO’VE NOW BEEN MARRIED 20 YEARS. Karen Fairchild and Jimi Westbrook weren’t a couple when Little Big Town started. Not even close. Karen went through a divorce after their first album. Jimi happened to be single around the same time. And something between them changed — but neither of them wanted to admit it. Because the band meant everything. One wrong move could wreck years of work. Their bandmate Phillip Sweet later said he and Kimberly would watch those two butt heads on tour and whisper to each other, “They just need to go for it already.” On May 31, 2006, Karen and Jimi quietly got married in Nashville. No announcement. No fanfare. They kept it to themselves for months. Twenty years and one son later, they still share the same stage, the same tour bus, the same life.

How Karen Fairchild and Jimi Westbrook Built a Love Story Without Breaking the Band

Long before anyone called them a power couple, Karen Fairchild and Jimi Westbrook were just two members of Little Big Town trying to make  music work. They were bandmates first, friends second, and something more only in the quiet spaces they did not know how to name yet. As Kimberly Schlapman later said, “We knew they were in love before they knew they were in love.”That is what makes their story feel so human. Love did not arrive with a grand announcement. It crept in while they were touring, recording, and building a career that depended on trust. At the start of Little Big Town, Karen Fairchild and Jimi Westbrook were not a couple at all. Life simply lined them up at the same moment: Karen went through a divorce after the band’s first album, and Jimi happened to be single around the same time.

What changed between them was subtle at first. A look that lingered too long. A joke that landed a little differently. A tension that could not quite be explained. But neither Karen Fairchild nor Jimi Westbrook wanted to risk what they had built. The band was bigger than any one relationship, and one wrong move could have shaken years of hard work.

“They just need to go for it already.”

That was the kind of thing Phillip Sweet and Kimberly Schlapman would quietly say to each other while watching Karen Fairchild and Jimi Westbrook on tour, according to the band’s own shared memories. The signs were there for everyone except the two people living them. They would butt heads, circle around the truth, and keep performing night after night as if the stage could hold all the feelings they were trying not to admit.

Then, on May 31, 2006, Karen Fairchild and Jimi Westbrook made their choice. They got married in Nashville in a quiet ceremony, with no big announcement and no public celebration. For months, they kept it private, protecting the relationship the same way they had protected the band: carefully, patiently, and with a clear sense that some things matter more when they are not turned into a spectacle.

Twenty Years Later, the Story Still Feels Fresh

Two decades later, Karen Fairchild and Jimi Westbrook are still doing what many couples struggle to do: sharing a life without losing the friendship underneath it. They are still part of Little Big Town. They still share the same stage, the same tour bus, and the same daily rhythm that has carried them through success, change, and time.

They also share a son, which gives their story another layer of meaning. It is not just a love story. It is a life story, built in public but guarded with real intention. The fact that Karen Fairchild and Jimi Westbrook have stayed together for 20 years says something about commitment, but it also says something about timing. Sometimes love is not loud at first. Sometimes it arrives as patience, respect, and the decision to protect something fragile until it is strong enough to stand on its own.

That is why Kimberly Schlapman’s observation still lands so well. The rest of the world may have seen only band chemistry, shared work, and a little friction on the road. But the people closest to them could see the truth before they could say it out loud. Karen Fairchild and Jimi Westbrook did not just fall in love. They had to grow into it, while keeping the music alive.

And maybe that is the most lasting part of all: not that they became a couple, but that they managed to become one without losing the band that brought them together in the first place.

 

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Old pop standards were an unexpected choice for country music’s biggest outlaw. But in 1977, Willie Nelson wanted to record songs he’d loved since childhood: “Stardust,” “Blue Skies,” “Moonlight in Vermont,” and “Someone to Watch Over Me.” Several were older than he was. His contact at Columbia Records pushed him to write new material. Willie knew younger fans might not recognize the songs, but their parents and grandparents would. Booker T. Jones, his Malibu neighbor, agreed to produce. Willie’s main concern was “Georgia on My Mind.” After Ray Charles, what could he bring to it? Booker’s answer was simple: “Ray did it his way, and you’ll do it yours.” They recorded the album in ten days at a Hollywood Hills house. Mickey Raphael even played his harmonica parts from inside a tiled bathroom shower. Columbia initially pressed a smaller run than usual, then had to order more. “Georgia” reached No. 1 and earned Willie a Grammy. Stardust sold roughly five million copies and stayed on the country albums chart for 540 weeks. Willie brought his own voice to songs associated with Sinatra and Ray Charles. Familiar music sounded unmistakably like him, and his audience embraced it.

First Baptist Church in Hendersonville had hosted June Carter Cash’s funeral less than four months before mourners returned to say goodbye to Johnny. His death on September 12, 2003, left the Tennessee town and the music community struggling with a second loss. For those who had known them away from the stage, the sanctuary held the grief of losing a couple whose lives had been so closely joined. More than a thousand people gathered for the service. Kris Kristofferson, George Jones, and Vince Gill were among them, mourning a friend whose life had crossed decades of Nashville history. Amid the solemn arrangements, one wreath stood out: raw cotton, corn, and turnip plants recalled the Arkansas soil and hard beginnings of the Cash family. It was a simple connection to the life behind the fame. During a biographical film, Johnny’s voice filled the church again, bringing the year’s losses into painful focus. Rosanne Cash sat in the front row as the congregation listened. Others were remembering a legend; she was confronting life without her father. The familiar voice was still there to hear, but she could no longer answer him. What had once been part of their everyday connection now remained as a recording, carrying his presence into history.

Billy Joe Shaver had a show booked near Austin on December 31, 2000, the day his son Eddy died at 38. He had already lost his wife and mother the previous year. Losing his child and musical partner left him barely able to think about performing. He couldn’t even find his band members, while showtime drew closer. Willie Nelson stepped in. A friend since the 1950s, he assembled musicians and took charge so Billy Joe wouldn’t have to face the night alone. Willie guided the set, giving his friend something steady to hold onto. When Shaver reached the microphone, his performance was fragile, sustained by determination rather than precision. The audience in the smoky room understood the effort it took for him to be there. Afterward, they went to Willie’s home and talked away from the crowd. As the night wore on, the enormity of Eddy’s death began to settle in. Music and fame mattered little beside the simple need to keep a grieving friend from becoming lost in his sorrow. By dawn, Billy Joe had made it through those first terrible hours with Willie beside him. Between conversation and silence, two men familiar with the hardships of the road had found the beginnings of a way forward.

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Country

Old pop standards were an unexpected choice for country music’s biggest outlaw. But in 1977, Willie Nelson wanted to record songs he’d loved since childhood: “Stardust,” “Blue Skies,” “Moonlight in Vermont,” and “Someone to Watch Over Me.” Several were older than he was. His contact at Columbia Records pushed him to write new material. Willie knew younger fans might not recognize the songs, but their parents and grandparents would. Booker T. Jones, his Malibu neighbor, agreed to produce. Willie’s main concern was “Georgia on My Mind.” After Ray Charles, what could he bring to it? Booker’s answer was simple: “Ray did it his way, and you’ll do it yours.” They recorded the album in ten days at a Hollywood Hills house. Mickey Raphael even played his harmonica parts from inside a tiled bathroom shower. Columbia initially pressed a smaller run than usual, then had to order more. “Georgia” reached No. 1 and earned Willie a Grammy. Stardust sold roughly five million copies and stayed on the country albums chart for 540 weeks. Willie brought his own voice to songs associated with Sinatra and Ray Charles. Familiar music sounded unmistakably like him, and his audience embraced it.

Country

First Baptist Church in Hendersonville had hosted June Carter Cash’s funeral less than four months before mourners returned to say goodbye to Johnny. His death on September 12, 2003, left the Tennessee town and the music community struggling with a second loss. For those who had known them away from the stage, the sanctuary held the grief of losing a couple whose lives had been so closely joined. More than a thousand people gathered for the service. Kris Kristofferson, George Jones, and Vince Gill were among them, mourning a friend whose life had crossed decades of Nashville history. Amid the solemn arrangements, one wreath stood out: raw cotton, corn, and turnip plants recalled the Arkansas soil and hard beginnings of the Cash family. It was a simple connection to the life behind the fame. During a biographical film, Johnny’s voice filled the church again, bringing the year’s losses into painful focus. Rosanne Cash sat in the front row as the congregation listened. Others were remembering a legend; she was confronting life without her father. The familiar voice was still there to hear, but she could no longer answer him. What had once been part of their everyday connection now remained as a recording, carrying his presence into history.

Country

Billy Joe Shaver had a show booked near Austin on December 31, 2000, the day his son Eddy died at 38. He had already lost his wife and mother the previous year. Losing his child and musical partner left him barely able to think about performing. He couldn’t even find his band members, while showtime drew closer. Willie Nelson stepped in. A friend since the 1950s, he assembled musicians and took charge so Billy Joe wouldn’t have to face the night alone. Willie guided the set, giving his friend something steady to hold onto. When Shaver reached the microphone, his performance was fragile, sustained by determination rather than precision. The audience in the smoky room understood the effort it took for him to be there. Afterward, they went to Willie’s home and talked away from the crowd. As the night wore on, the enormity of Eddy’s death began to settle in. Music and fame mattered little beside the simple need to keep a grieving friend from becoming lost in his sorrow. By dawn, Billy Joe had made it through those first terrible hours with Willie beside him. Between conversation and silence, two men familiar with the hardships of the road had found the beginnings of a way forward.

Country

NINETEEN HITS FELL SHORT BEFORE THE TWENTIETH CHANGED EVERYTHING. By the late summer of 1978, the tension inside the recording studio was palpable. Barbara Mandrell had managed to land nineteen consecutive songs on the country charts, yet the top spot remained an elusive ghost. She was a working professional, delivering exactly what the machine demanded, but the absence of a chart-topper felt like a structural failure. The air was thick with the silent frustration of an artist who knew she was capable of more, waiting for the one song that would finally validate the grind of the previous decade. Her producer, Tom Collins, recognized that the formula had gone stagnant. He brought in two young, hungry writers, Kye Fleming and Dennis Morgan, looking for something that broke the mold. He didn’t come with a pitch about industry trends; he came with a simple, personal photograph of his own wife’s grandparents, still sharing their small, worn bed after all those years. It was an intimate, domestic image that felt worlds away from the slick, calculated production of Nashville’s mainstream output at the time. The writers took that quiet image and inverted the emotion, crafting a story not about enduring love, but about the hollow coldness of being left alone in a bed built for two. When Barbara stepped to the microphone to record it, the mood shifted. In November, that vulnerability paid off as ‘Sleeping Single in a Double Bed’ seized the No. 1 position, where it held firm for three weeks. The struggle that had defined her career for years vanished in an instant, replaced by the weight of a signature hit that would eventually earn international acclaim and redefine her path as a country superstar.