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Greatest Hits Oldies But Goodies Ever

When Randy Owen married Kelly in Alabama on February 11, 1975, he had no money in the bank and sang six nights a week for tips in a glass jar. Raised on a sharecropper farm without indoor plumbing on Lookout Mountain in Fort Payne, Owen grew up picking cotton and chopping wood before earning an English degree at Jacksonville State University. At 25, he was fronting an unknown group called Wildcountry with his cousins Teddy Gentry and Jeff Cook. From 1973 to 1979, the trio played nightly at The Bowery in Myrtle Beach, South Carolina. Kelly gave up a stable life to share cramped rentals with him, stretching spare change to cook dinners of potatoes and beans while washing stage clothes, packing gear, and selling T-shirts and homemade cassettes alongside the other wives. By the late 1970s, after Nashville labels repeatedly rejected them because executives doubted a country band could sell records, Owen was ready to quit music and take a manual job to support his home. Kelly held his hand and asked him to keep going a little longer. In 1980, the group changed its name to Alabama, signed with RCA Records, and began a run that produced more than 80 million record sales and a 2005 induction into the Country Music Hall of Fame. Owen later bought land at the foot of Lookout Mountain in Fort Payne to build their Tenasi ranch where he had once grown up poor. Half a century after their quiet 1975 wedding, having raised their three children, Alison, Heath, and Randa, and stood together through his 2010 prostate cancer treatment, he still credits everything they built to the woman who believed in him when their living came out of a barroom tip jar.

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When Randy Owen married Kelly Rosanne Pyle on February 11, 1975, the twenty-five-year-old singer was earning his living out of a glass tip jar at a coastal bar in Myrtle Beach, South Carolina, while his bride helped count the spare change to buy groceries.

Long before Alabama became the most successful band in country music history, Owen grew up in the DeKalb County community of Adamsburg near Fort Payne, Alabama, living on a small Lookout Mountain farm without indoor plumbing. Alongside his parents, Gladstone and Martha Owen, and his two sisters, he spent his childhood plowing rented row-crop fields, picking cotton, and chopping wood before becoming the first member of his family to graduate from college with an English degree from Jacksonville State University.

Even with a degree in hand, Owen returned to music alongside his cousins Teddy Gentry and Jeff Cook in a band first called Young Country and then Wildcountry. In March 1973, the trio loaded their gear and moved to Myrtle Beach to take a house band job at a tavern called The Bowery, playing six nights a week for tips.

Two years into that coastal grind, Owen and Kelly married in February 1975. Leaving behind a steady life at home, Kelly moved into cramped Myrtle Beach rentals with him while the band spent seven summers playing cover tunes from Lynyrd Skynyrd to Merle Haggard for vacationers and bikers.

Money was so scarce during the off-seasons that the couples pooled coins to cook pots of beans and potatoes. Behind the scenes, Kelly and the other band wives washed stage clothes, packed equipment, managed the books, and sat near the door selling band T-shirts and self-financed eight-track and cassette tapes that the cousins recorded between bar sets.

By the late 1970s, after changing their name to Alabama in 1977, the group still could not convince major Nashville labels that a self-contained country band playing its own instruments could sell records. Exhausted by the rejections and worried about supporting a household, Owen came close to walking away from music to take a regular labor job back home.

Kelly held his hand and asked him to stay with the band a little longer. That persistence paid off when Alabama charted on the independent Dallas label MDJ Records and signed with RCA Records in April 1980, launching a streak of twenty-one consecutive No. 1 singles, more than eighty million albums sold, and a 2005 induction into the Country Music Hall of Fame.

Instead of moving permanently to Nashville when the checks arrived, Randy and Kelly returned to Lookout Mountain in Fort Payne. Beginning with their first purchase of Hereford cattle in 1981, Owen bought back the exact tracts of DeKalb County land his family had once sharecropped and rented, expanding the property into a 3,000-acre working cattle operation named Tennessee River Music and building their home, Tenasi, bordered by Little River Canyon.

The ranch also carried an early personal loss. In 1981, just as Alabama swept the Country Music Association Awards, Owen’s father died unexpectedly while Randy was out on the road, leaving Randy and Kelly to carry forward the purebred cattle operation that father and son had planned together on long drives to livestock sales.

While Owen toured for hundreds of nights a year, Kelly anchored their Fort Payne household and raised their three children, Alison, Heath, and Randa. In 1989, Kelly and the children also sat at home helping organize the early outreach for Owen’s Country Cares for St. Jude Kids radiothon, a fundraising effort that grew across country radio to raise more than $800 million for St. Jude Children’s Research Hospital.

Their partnership weathered another test in 2010 when Owen was diagnosed with prostate cancer, with Kelly staying beside him through treatment and recovery. Fifteen years later, after celebrating their fiftieth wedding anniversary in February 2025, Randy and Kelly traveled to Kansas City together in November 2025 to accept the American Hereford Association Hall of Merit Award for the Fort Payne ranch they still run side by side with their daughter Randa and son-in-law.

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In 1965, Kris Kristofferson turned down a teaching post at West Point to sweep floors and empty ashtrays for $58 a week at Columbia Recording Studios in Nashville. An Oxford Rhodes Scholar, Army captain, and helicopter pilot, he gave up a secure future and faced his parents’ disapproval just to work night shifts near Johnny Cash. Standing behind the studio glass after cleaning hallways, he watched Cash record, and in the late 1960s he shared a cramped Nashville apartment with Waylon Jennings while trying to get his songs heard. After years of unanswered demos, Kristofferson landed a National Guard helicopter on Cash’s lawn to hand him a tape of Sunday Mornin’ Comin’ Down. Cash recorded the song, brought the former janitor onto The Johnny Cash Show, and helped propel him to the 1970 CMA Song of the Year award. Following a 1984 Christmas television special in Switzerland, Kristofferson joined Cash, Jennings, and Willie Nelson in 1985 to form The Highwaymen. Across ten years, world tours, and three albums, the Golden Globe winner still viewed his three bandmates as country music’s Mount Rushmore and himself as a grateful kid let into the picture. That era closed when Jennings died on February 13, 2002, at age 64, followed by Cash on September 12, 2003, at 71, where Kristofferson wept beside his mentor’s casket in Hendersonville. Looking back in 2010, he admitted through tears that when the four of them were laughing on the tour bus, he never stopped long enough to realize how quickly those years with his heroes would pass. In the years before he passed away at home in Maui on September 28, 2024, at age 88, Lyme disease and memory loss faded much of his daily recall. Even then, his family said hearing the names of Cash, Jennings, and Nelson or the music of The Highwaymen always brought the light straight back to his eyes.

After crying through the writing of a wedding song for his oldest daughter Mattie in 2017, Alan Jackson told his younger girls they would all have to share it. Raised in Newnan, Georgia, with four sisters, Connie, Cathy, Carol, and Diane, Jackson later built a home surrounded by women with his wife Denise and their three daughters, Mattie Denise, born in 1990, Alexandra Jane, known as Ali, born in 1993, and Dani Grace, born in 1997. Even the family dogs were female. Away from the white cowboy hat on stage, his daughters knew a father who cleaned their scraped knees, listened to their troubles for hours, and stood by Mattie through the grief of losing a husband eleven months into marriage. In the summer of 2017, ahead of Mattie’s September wedding in southern Florida, Jackson sat alone with his guitar to write You’ll Always Be My Baby (Written for Daughters’ Weddings). Memories of his girls running across the yard as children choked him up so often that he had to stop repeatedly while writing and recording the song. Accustomed to singing before tens of thousands of fans, Jackson admitted that walking his daughter down the aisle without weeping was the hardest thing he had ever done. Unwilling to put his heart through that writing process a second time, he told Ali and Dani that one song would have to cover all three weddings, then relented in 2020 when Ali married and Dani got engaged, writing a second ballad titled I Do (Written for Daughters’ Weddings). Both tracks were meant solely for the family receptions until Jackson released them on his twenty-first studio album, Where Have You Gone, on May 14, 2021, his first new album in six years. That year, he also revealed a decade-long battle with the degenerative nerve disease Charcot-Marie-Tooth, having finished both wedding songs while his hands and voice remained steady enough for his daughters’ wedding dances.

Across a career of more than six decades that brought eleven Grammy Awards, over 100 million records sold, nominations for the Oscar, Emmy, and Tony Awards, and induction into both the Country Music and Rock & Roll Halls of Fame, Dolly Parton always pointed to a bronze statue on the courthouse lawn in Sevierville, Tennessee, as the honor that touched her heart the deepest. Unveiled on May 2, 1987, the sculpture by late artist Jim Gray was not funded by a government agency or a major entertainment corporation. Instead, the neighbors and residents of Sevier County pooled their own money to place her likeness in front of the historic 1896 Sevier County Courthouse, the civic heart of East Tennessee typically reserved for local historical heroes. That courthouse square held hard childhood memories for the fourth child of a fourteen-member sharecropping family. In the 1950s, whenever young Dolly came down from isolated Locust Ridge into town barefoot in a dress sewn from cornmeal sacks, some townspeople looked down on her or teased her for her family’s poverty. Right on those courthouse steps, she once stood staring out at the town while her father, Robert Lee Parton, drove his wagon in through bitter winter cold and summer heat to sell farm goods for spare change to feed his children. Unlike gold trophies handed out by industry panels in distant cities, the bronze statue came from the very community that had known her when she had nothing, offering a lasting embrace to the mountain girl who had once stood on those stone steps. The honor meant even more to her father. Robert Lee Parton never fully grasped the scale of his daughter’s Grammy Awards or platinum records far from home, yet seeing her cast in bronze on the county square gave him tangible proof that his daughter had brought honor to the family name. Before his passing in 2000, he often drove his old pickup truck down to the courthouse late at night after the town had gone to sleep, carrying a bucket of soapy water and a brush to quietly scrub pigeon droppings off the bronze shoulders of his little girl.

In early 1994, while listening to Vince Gill record his guitar solo on House of Love in Nashville, Amy Grant walked up behind him and wrapped her arms around him. The two had first met in late 1993 at a televised A Country Christmas benefit in Nashville, where Grant later said she felt an immediate connection with him. When she invited Gill to sing and play on the title track of her tenth studio album a few months later, his warm vocal and guitar work moved her so deeply in front of the production crew that she hugged him tightly and said she wished she could hold him all night. Gill stood still, gently patted her hand, and did not cross the line. Both were married at the time, Gill to Janis Oliver since 1980 and Grant to Christian musician Gary Chapman since 1982. Though Grant was widely seen as an ideal symbol of Christian family life, she was privately lonely in a strained marriage. Crew members noticed the same quiet intensity when the pair filmed the House of Love music video later in 1994. Still, both returned home and kept their distance for years, staying in touch mainly through Nashville charity golf tournaments while Gill occasionally sent her golf clubs and friendly greetings. After years of trying to repair marriages that were already coming apart, Gill divorced in 1998 and Grant finalized her divorce in 1999. Christian radio stations boycotted Grant’s records and conservative listeners judged her harshly, while Gill stood steady beside her and her children. On March 10, 2000, they married on a quiet hillside near Nashville, turning the connection that began in that 1994 studio session into a marriage that has lasted more than two decades.

On May 2, 1987, thousands of East Tennessee neighbors crowded the streets around the Sevier County Courthouse in Sevierville to unveil a six-and-a-half-foot bronze statue of Dolly Parton paid for through donations from her own hometown community. To create the tribute, local residents turned to artist Jim Gray, a painter known across the Great Smoky Mountains for his watercolors and oils rather than large-scale sculpture. Stepping away from his easel out of shared love for their mountain home, Gray spent more than two thousand hours in his studio shaping clay before the figure was cast in solid bronze. It became one of only three major sculptures he ever completed in his life, alongside the World War I Doughboy memorial in Knoxville and his pioneer monuments on Broadway. Instead of depicting Parton under arena lights in sequined stage gowns, Gray sculpted her as a barefoot mountain girl sitting comfortably on a large rock with an acoustic guitar resting in her lap, just as she used to sit and sing as a child. He worked every small detail into the clay, from her warm smile and cascading curls to her long fingers on the strings and a small butterfly resting nearby. Standing on the courthouse lawn that May afternoon, Parton told her neighbors that out of every award she had received around the world, having the people who raised her place her likeness on the very square where her father once drove his wagon was the greatest honor of her life. Her father, Robert Lee Parton, an illiterate farmer who had worked the county’s hard soil his whole life, stood in the crowd that day watching his daughter honored in front of the county’s most formal building. Parton later shared that she once caught her father slipping out to the courthouse at night in his old pickup truck with a bucket of water and a rag to quietly wash bird droppings off his daughter’s bronze shoulders. When Jim Gray passed away in December 2019 at age eighty-seven, he left behind thousands of paintings, yet the barefoot girl with the guitar on the Sevierville lawn remained his most visited work, still guarded by the pride of a mountain town and a father’s midnight bucket of water.

After a cycling crash in Nashville left Amy Grant with a traumatic brain injury in July 2022, Vince Gill canceled his August tour dates to care for her at home. On July 27, 2022, Grant was riding with a friend in Percy Warner Park when her wheel hit a pothole and threw her onto the pavement. Knocked unconscious for more than ten minutes, she was rushed to Vanderbilt University Medical Center, where doctors said her helmet saved her life. The accident arrived just two years after her June 2020 open-heart surgery. The brain injury affected her balance and short-term memory, and a throat surgery soon after left her voice raspy. For a time, she struggled to recall songs she had performed for forty years and had to postpone her fall concerts. Gill called off his own shows across the East and South to stay with her. Neurologists ordered strict rest away from phones, television, bright lights, and music, turning a Nashville home normally filled with guitars into a place of quiet. Gill put his instruments aside, cooked meals, sat with her on the porch, and gently repeated daily details as she used a small notebook to rebuild her memory. Even as she feared losing her singing ability, he assured her that her worth to him and their family never depended on singing another note. By December 2022, nearly five months after the fall, Grant arrived at the Kennedy Center Honors in Washington, D.C., as the first contemporary Christian artist to receive the distinction. After holding her hand on the red carpet, Gill stepped onstage and sang in her honor, his voice catching as he looked up at the wife he had spent months helping heal in silence.

When Mark Knopfler invited Vince Gill to tour the world as a member of Dire Straits, the struggling Nashville singer was nearly broke and still said no. After fronting Pure Prairie League, Gill watched three solo albums for RCA, The Things That Matter, The Way Back Home, and Cinderella, earn critical praise but weak sales. By 1988 he had lost his record deal and was supporting his wife Janis Oliver and their daughter Jenny through Nashville studio sessions paying a few hundred dollars a call. One of those calls brought him in to sing backup on The Bug for Dire Straits. Frontman Mark Knopfler, one of Gill’s guitar heroes, was so impressed by his tenor voice and guitar playing that he offered the Oklahoma native a full-time spot on a two-year world tour. Following the massive success of Brothers in Arms, the British rock band was filling arenas worldwide, and the job promised immediate financial security. Gill still declined, unwilling to board a tour jet and spend the rest of his life wondering whether he could have made it on his own in country music. Knopfler respected that decision, and the two stayed friends while Gill signed with producer Tony Brown at MCA Records in 1989. Later that year, he released When I Call Your Name, pouring years of quiet persistence into a title track paired with the harmony vocals of Patty Loveless. The album went Double Platinum, and the title song won Single of the Year at the 1990 CMA Awards to a standing ovation at the Grand Ole Opry House before bringing Gill his first Grammy in early 1991. That breakthrough began a run of 22 Grammy Awards for a singer who refused the easy exit when his pockets were empty.

Across eighty-two years of life and more than six decades on the country music stage, Hank Thompson never had a biological child of his own to pass down his guitar or his cowboy hat. For a traditional Southern man who spent his life singing about home and heartache, that quiet absence remained a private ache he rarely spoke about or complained of in interviews. Neither his earlier marriage to Dorothy Jean Ray nor his thirty-seven-year marriage to Ann Williams from 1970 to 2007 brought children into the house. Rather than letting that emptiness pull them apart, Hank and Ann leaned completely into each other, understanding that as the years went on, they were each other’s truest family. Between tours at their ranch near Roanoke and Keller, Texas, the couple built a quiet rhythm together, tending their horses, dogs, and the yard around their home. Yet their house did not stay silent. With no children of their own by blood, Hank and Ann opened their doors and their lives to the generations of young musicians who joined his longtime band, the Brazos Valley Boys. Out on the highway for more than two hundred nights a year, Thompson never treated his bandmates like hired hands. He guided the young players the way a father raises his sons, teaching them how to tune their instruments, dress with pride under the stage lights, carry themselves professionally, and save their road pay to send back to their families. Whenever the tour bus rolled back to Texas for holidays or breaks between runs, Ann cooked home-cooked meals and welcomed the band to the ranch, filling a childless house with the noise and warmth of a large family table. When Thompson spent his final days at home in November 2007 at age eighty-two, Ann was not the only one keeping watch by his bed. Beside his wife of nearly four decades stood the former and current members of the Brazos Valley Boys, the musical sons who came home to make sure the man who raised them in the trade never left this world alone.

When Alan Jackson first played the demo of Remember When for his wife Denise in their kitchen, it held the truth of a marriage they had nearly lost. Their story started at a Dairy Queen in Newnan, Georgia, in 1976, and they married on December 15, 1979, when Alan was 21 and Denise was 19. In 1985, while working as an Eastern Airlines flight attendant, Denise spotted Glen Campbell at the Atlanta airport and asked for his management contact, opening the door that brought her husband to Nashville. Success came quickly over the next decade, along with three daughters and heavy touring schedules. By 1998, the constant distance and Alan’s infidelity pushed nearly twenty years of marriage to the edge, leading to a four-month separation. Living apart from his family became a painful wake-up call for the singer. Through marriage counseling, their Christian faith, and quiet dinner and movie dates that allowed them to start over, Alan and Denise slowly rebuilt the trust that fame had damaged. Five years after the separation, Alan secretly wrote Remember When as a candid musical diary of their youth, raising their daughters, the fracture they survived, and the years still ahead of them. Hearing that unfinished recording at home for the first time, Denise broke down in tears, and she later stepped in front of the camera to dance with him in the music video beside real family footage. Released in October 2003, the song reached No. 1 on the Billboard country chart in early 2004, and Denise shared their story of forgiveness in her 2007 bestselling memoir. In 2010, Alan stepped back from his schedule to stay by her side through chemotherapy and radiation for colorectal cancer until her recovery, living out the vows behind the 1979 wedding photo that still shines on stage whenever he sings the song.