At Christmas in 2001, Waylon Jennings asked Jessi Colter to sit at the piano and sing the hymns she’d grown up playing in church. Diabetes had taken much of his strength. He wanted to hear those old songs. Jessi, the daughter of a Pentecostal preacher in Phoenix, had been playing piano in her mother’s church since she was eleven. Waylon had grown up hearing fire-and-brimstone sermons in Texas and walked away from religion as a young man. For most of their 32 years of marriage, faith was something Jessi had largely kept to herself. A month before Christmas, on Thanksgiving Day, she sat beside his hospital bed and asked if he was ready to accept the Lord. Waylon grinned. He knew she was going to ask, he told her. Then he said yes. Jessi later wrote that she wept. That Christmas, she played and he listened. Jessi remembered a quiet assurance in him by then. She felt he’d made his peace. Waylon died at home in Chandler, Arizona, on February 13, 2002. He was 64. Four years later, Jessi released *Out of the Ashes*, her first new solo album since 1984. Waylon’s voice appears on “Out of the Rain,” a Tony Joe White song the three of them had recorded together years before. The album opens with “His Eye Is on the Sparrow.” Jessi had sung it to warm up, and producer Don Was decided to keep the take. It was a hymn both Waylon and her mother had loved.

At Christmas 2001, with the family gathered in Arizona and diabetes wearing his body down, Waylon Jennings asked his wife, Jessi Colter, to sit at the piano and sing the…

Don Williams had already played a sold-out farewell concert when he retired for the first time. Ten years later, he said goodbye in two sentences. His 2006 “Farewell Tour of the World” ended on November 21 at the Cannon Center in Memphis. The plan was to go home to the farm with his wife, Joy. By 2010, though, the Gentle Giant was touring again, and he went on to make two more albums. In early 2016, Williams had 21 cities on his schedule. The first show was set for February 17 at the Florida Theatre in Jacksonville. But on February 2, his publicist announced that Williams had undergone unexpected hip replacement surgery. The tour was canceled, and ticket holders were directed to the venues for refunds. Four weeks later, on March 1, Williams announced his retirement. He was 76. “It’s time to hang my hat up and enjoy some quiet time at home,” he said. Then he thanked his fans, his friends, and his family. This time, there would be no farewell tour or final concert. Williams had about eighteen months at home before he died of emphysema on September 8, 2017, in Mobile, Alabama. He was 78. He and Joy had been married for 57 years.

On March 1, 2016, Don Williams announced he was retiring from country music. He was 76. It was the second time he had said goodbye in ten years, and the…

Sammy Kershaw had already moved tour dates and booked flights and a hotel when, he says, the Country Music Association told him he couldn’t walk the red carpet at its 2026 awards show. He’d asked for a few minutes on the arrivals line with his wife, Mendy. This year’s show was set to salute ’90s country, the era that made him a star. Kershaw said the couple rarely gets to attend industry events because he’s usually on the road. They’d walked the carpet before, and Getty photographers captured him arriving at the 50th CMA Awards in 2016. This time, he said, they waited months for an answer. In a November 5 Facebook post, the 68-year-old explained why the decision stung. He’d been a lifetime CMA member since 1992, earned a Horizon Award nomination in 1993, and spent more than 50 years in music, with more than two dozen hits on the Billboard charts. He also recalled playing a CMA Fest show without pay at the association’s request. He called the decision hurtful and embarrassing. The next time he was part of the CMAs, he wrote, might be in a tribute after he was gone. Thousands of fans responded. So did Riley Green, who covered Kershaw’s “Yard Sale” in 2022, days before the two shared a stage in Mississippi. “If you haven’t earned the right to be there then nobody has,” Green wrote.

In November 2026, two weeks before the 60th CMA Awards, Sammy Kershaw learned that the Country Music Association had turned down his request to walk the red carpet. The show…

Stonewall Jackson asked Tom T. Hall for a prison song. Hall kept trying to write one, but he’d never been to prison and couldn’t make the story sound right. His wife, Dixie, reminded him that he’d spent several days in a Kentucky jail. He could start there. It happened in Paintsville, where a traffic violation landed Hall in the county jail. The judge had gone out of town for a family funeral, so what should have been a short stay dragged on for nearly a week. With nowhere to go, Hall had plenty of time to take stock of the sheriff, the food, and how slowly a day could pass. He embellished some of the funny details when he put the story to music, but the wait was real. “A Week in a Country Jail” sounded like Hall telling the story across a kitchen table. It didn’t even have a conventional chorus. Producer Jerry Kennedy thought the song was so suited to Hall’s way of telling it that he encouraged him to record it himself. In January 1970, it became Hall’s first No. 1 as a recording artist. He would bring that same ear for ordinary conversation to “The Year That Clayton Delaney Died,” “Old Dogs, Children and Watermelon Wine,” and “Faster Horses.” In Paintsville, the detail that made the whole story work was the judge being out of town. Hall had spent days wishing the man would come back. Thanks to Dixie, he finally had a use for all that waiting.

TOM T. HALL WAS ASKED TO INVENT A PRISON SONG—HIS WIFE REMINDED HIM HE ALREADY HAD ONE Stonewall Jackson asked Tom T. Hall to write him a prison song. Hall…

One of Ricky Van Shelton’s demo tapes found its way to Columbia Records through someone Bettye worked with. By then, she had already encouraged him to move with her to Nashville when she was offered a job there. Her paycheck kept them going while he spent his days trying to get a record deal. Once he signed, things moved fast. From 1987 into the early 1990s, Shelton put a string of singles at No. 1 and won both the CMA Horizon Award and Male Vocalist of the Year. His traditional sound made him one of the leading voices in country music’s return to its roots. By 1991, at the height of that success, he was drinking heavily, deeply depressed, and watching his marriage come apart. That was how Shelton later described a year that looked very different to fans who knew him as a singer devoted to his faith and family. He had been drinking since he was young, he said, and the pressure and long stretches of boredom on tour made it worse. Shelton eventually quit drinking, and he and Bettye stayed together. In her own account of their marriage, she wrote openly about addiction and infidelity and about why she chose to stay when leaving was an option. Bettye had once helped Ricky take a chance on Nashville when there was no guarantee anyone would hear his records. Years later, when millions knew his voice, she had a much harder decision to make about the life they’d built together.

RICKY VAN SHELTON REACHED THE TOP OF COUNTRY MUSIC WHILE ALCOHOL WAS PULLING HIS MARRIAGE APART In 1991, Ricky Van Shelton looked like one of Nashville’s safest success stories. Platinum…

Long before global stadiums roared his name and history crowned him the King of Rock and Roll, Elvis Presley was simply a quiet, shy boy from Tupelo, walking the dusty paths of Mississippi with empty pockets, a beat-up guitar, and a heart overflowing with impossible dreams. He couldn’t possibly fathom that the melodies humming in his head would one day become the soundtrack to a generation, or that oceans of people would weep at the mere breath of his voice. Yet, even in those early days, long before the flashbulbs and the blinding lights of stardom, there was an ineffable magic tethered to his soul. It wasn’t just the blueprint of his striking face or the natural, subterranean gift of his voice—it was the profound gentleness in his spirit. It was the way he looked people in the eye with unfeigned humility, the quiet kindness he extended to strangers, and an innate, luminous warmth that made anyone standing near him feel entirely seen. Even then, before the world knew his name, you could feel it in the air: a rare, tender light that belonged to someone extraordinary, quietly waiting for the world to catch up.

Before the world called him the King of Rock and Roll, Elvis Presley was just a young boy with very little money, a heart full of dreams, and a future…

On August 16, 1977, the music didn’t just fade; it was shattered by an abrupt, deafening silence that echoed across the globe. Elvis Presley was only forty-two when he slipped away behind the familiar gates of Graceland—the sanctuary he had built with his own hands to keep his family safe from the crushing storms of fame. There was no final curtain call, no parting melody drifting from a stage, and no quiet moment for the millions who loved him to whisper a proper farewell. The man who had soundtracked the world’s greatest joys, eased its deepest heartaches, and taught generations how to feel was suddenly gone in an instant. Yet the truest tragedy wasn’t just the suddenness of his departure, but the heavy, invisible burden he carried in the shadows. Beneath that legendary smile and the blinding lights of the arena, he was fighting a lonely, exhausting war against his own breaking body and spirit—battles he bore in total solitude, leaving behind a grief that time has never been able to mend.

On August 16, 1977, a voice that had filled the world with music suddenly fell silent. Elvis Presley was only 42 years old when he was found unresponsive inside Graceland,…

History is filled with striking faces, but Elvis Presley possessed a rare, devastating symmetry that made the entire world fall hopelessly in love—and left it unable to ever fully recover. Those unforgettable blue eyes, the heartbreaking curve of his smile, the midnight-dark hair, and features so flawless they seemed almost sculpted by a dream combined to make him the undisputed aesthetic icon of his generation. Yet static portraits could never truly hold him. The real magic lived just beneath the surface: a radiant, all-encompassing warmth in his gaze, a quiet tenderness that tempered his confidence, and an uncanny, intimate grace that made every single person in a sea of thousands feel as though he had caught their eye and smiled just for them. Nearly half a century after he left us, we still gaze at those faded photographs and wonder at the sheer, impossible alchemy of a man who held the beauty of an era, yet carried the fragile, beating heart of a boy from Tupelo.

Some men are remembered for their beauty, but Elvis Presley had the kind of face that made the world fall in love and never completely recover. Those unforgettable blue eyes,…

There’s a grin behind Toby Keith’s “How Do You Like Me Now?!” that makes its wounded pride even more entertaining. Co-written with Chuck Cannon and released in November 1999, it spent five weeks atop Billboard’s country chart and became the biggest country hit of 2000. I’ve always enjoyed the satisfaction in its story: the small-town boy dismissed in high school finally gets his chance to be heard. Toby gives him plenty of swagger, but you can still hear how much the rejection stung. That lingering hurt makes the boast work. He’s successful now—and he wants someone who doubted him to notice.

Toby Keith’s How Do You Like Me Now?!: A Triumphant Ballad of Redemption Toby Keith’s How Do You Like Me Now?! is more than just a country anthem; it’s a…

Toby Keith had a gift for telling a ridiculous barroom story as though it had happened to someone you knew. In “The Size I Wear,” co-written with Rivers Rutherford for his 2012 album *Hope on the Rocks*, two friends settle in for beers before a group of secretaries gives the evening a new direction. What I enjoy most is the mischief in his delivery. He lets the situation get out of hand without sounding remotely surprised. A few drinks, a little misplaced confidence, and suddenly there’s a story somebody will have to explain the next morning. Toby knew exactly how to land that kind of joke.

Toby Keith’s “The Size I Wear”: A Deep Dive into Americana Toby Keith’s “The Size I Wear” is more than just a catchy country tune; it’s a cultural artifact that…

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