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Greatest Hits Oldies But Goodies Ever

On the evening of June 13, 2020, twenty-seven-year-old Katherine “Katie” Williams-Dunning, the youngest daughter of country music star Hank Williams Jr. and his third wife, Mary Jane Thomas, lost her life in a single-vehicle crash on U.S. Highway 79 near Paris, Tennessee. Just hours earlier, Katie had shared a family photograph from a weekend trip by the lake with her husband, Tyler Dunning, whom she had married in October 2015, and their two young children. At around 7:44 p.m. in Henry County, the 2007 Chevrolet Tahoe she was driving southbound while towing a boat crossed the grassy median and rolled across the northbound lanes. Katie died at the scene, while twenty-nine-year-old Tyler survived with serious injuries and was airlifted to Vanderbilt University Medical Center in Nashville. Away from the stages that defined the Williams family name, Katie had built a quiet home life centered on her son, Beau Weston, born in 2017, and her daughter, Audrey Jane, born in 2019. She had given her baby girl the middle name Jane to honor her mother, Mary Jane, and combined her children’s and mother’s middle names to launch Weston Jane, a handmade clothing line supporting single mothers. At the June 2020 funeral in Paris, Hank Williams Jr. and Mary Jane stood side by side with their son, Sam Williams, to say goodbye to Katie. In the months that followed, Mary Jane stepped in to help care for the two young grandchildren left behind while carrying the weight of losing her only daughter and closest companion. The grief of that June evening on Highway 79 weighed heavily on Mary Jane’s health over the next twenty-one months. On March 22, 2022, less than two years after saying goodbye to Katie, Mary Jane passed away in Florida at age fifty-eight, leaving Sam and Hank Jr. to carry the memory of both mother and daughter through the two young children who still bear their family names.

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On October 21, 2020, what would have been his older sister’s twenty-eighth birthday, singer-songwriter Sam Williams released a tribute ballad titled “The World: Alone” four months after a highway crash in Henry County, Tennessee, took her life.

On Saturday evening, June 13, 2020, twenty-seven-year-old Katharine “Katie” Williams-Dunning—the daughter of country artist Hank Williams Jr. and his third wife, Mary Jane Thomas—was driving a 2007 Chevrolet Tahoe southbound on U.S. Highway 79 near Paris, Tennessee, while towing an eighteen-foot boat. At 7:44 p.m., the SUV crossed the grassy median and rolled across the northbound lanes, claiming Katie’s life at the scene and leaving her twenty-nine-year-old husband, Tyler Dunning, hospitalized at Vanderbilt University Medical Center.

Hours before the accident, Katie had posted a photograph from a weekend lakeside trip with Tyler, whom she had married on October 15, 2015, and their two young children: son Beau Weston, born in 2017, and daughter Audrey Jane, born in 2019. Rather than pursuing a stage career like her grandfather Hank Williams, her father, or her half-sisters Hilary and Holly, Katie had built her life in West Tennessee around motherhood and her handmade clothing company, Weston Jane, which she named by pairing her son’s middle name with the middle name she had given her daughter in honor of her mother, Mary Jane.

Following private services arranged through Ridgeway Funeral Home in Paris—where the family asked mourners to direct memorials to Tomorrow’s Hope Pregnancy Medical Clinic—Mary Jane stepped directly into daily caregiving for three-year-old Beau and one-year-old Audrey while Tyler recovered from his injuries.

Born in Daytona Beach, Florida, Mary Jane had been working as a Hawaiian Tropic model when she met Hank Williams Jr. at a concert on July 4, 1984. After marrying in Missoula, Montana, in 1990, the couple raised Katie and her younger brother, Samuel “Sam” Williams, in Paris, Tennessee, weathering a 2007 separation before reconciling in the years prior to Katie’s death.

While Mary Jane looked after Katie’s children, twenty-four-year-old Sam channeled the family’s loss into his debut album for Mercury Nashville, *Glasshouse Children*, released in August 2021. Alongside “The World: Alone,” the record included songs examining family fracture and survival, with guest appearances by Keith Urban and Dolly Parton.

Less than two years after Katie’s crash, the family suffered a second sudden loss. On March 22, 2022, fifty-eight-year-old Mary Jane died at Jupiter Medical Center in Jupiter, Florida, after developing a blood clot and a collapsed lung following a medical procedure.

In a public tribute announcing her passing, Hank Williams Jr. remembered the woman he had met on the Florida coast thirty-eight years earlier as a beach beauty who became a dedicated mother and a world-class hunter and adventurer alongside him. Sam shared wedding photographs of his parents, calling his mother a radiant spirit who took care of everyone around her.

Two days after Mary Jane’s death, Hank Jr. moved forward with the scheduled announcement of his fifty-seventh studio album, *Rich White Honky Blues*, recorded live with producer Dan Auerbach, and returned to the road that summer across North America, dedicating time offstage to his grandchildren.

Sam returned to the studio as well, releasing a deluxe edition of his debut album in October 2022 titled *Glasshouse Children: Tilted Crown*, which added the grief-steeped tracks “Ragdoll” and “Missing the Malice”. In June 2024, he followed it with his project *Act I: Scarlet Lonesome*, placing a sixty-five-second interlude at the heart of the tracklist titled “Heard Mary Jane Praying For Me”.

Out on the road and back home in Tennessee, Hank Williams Jr. and Sam continued recording and performing while watching Beau Weston and Audrey Jane grow up carrying the middle names Katie had chosen for her son and her mother.

https://www.youtube.com/watch?v=3cQNkIrg-Tk

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On March 3, 1963, despite battling a cold and a sore throat, Patsy Cline sang three unpaid benefit shows at Memorial Hall in Kansas City, Kansas, to raise money for the family of radio disc jockey Cactus Jack Call after his death in a car accident. She shared the bill with fellow country performers Cowboy Copas, Hawkshaw Hawkins, Billy Walker, Dottie West, and George Riddle. When dense fog grounded commercial flights the following day, West urged Cline to make the sixteen-hour drive back to Nashville with her and her husband. Eager to get home to her husband, Charlie Dick, and their young children, four-year-old Julie and two-year-old Randy, Cline declined the ride and boarded a four-seat, single-engine Piper Comanche piloted by her manager, Randy Hughes, at noon on March 5. Earlier, Billy Walker had left Kansas City on an urgent family matter after Hawkshaw Hawkins gave up a commercial ticket and took Walker’s seat on the small plane alongside Cline and Copas. After a first stop in Little Rock, Arkansas, the aircraft landed in Dyersburg, Tennessee, around 5:00 p.m. to refuel as heavy rain, gusting winds, and low clouds moved in. Inside the Dyersburg terminal, Cline called her mother, Hilda Hensley, who was watching the children in Nashville, to let her know she was on the final leg home. Although the airfield manager warned Hughes about severe storms ahead and offered overnight rooms or a rental car for the remaining drive, the group took off at 6:07 p.m. to reach their families that night. Thirteen minutes later, at 6:20 p.m., the plane lost orientation in the storm and crashed into a wooded area near Camden, Tennessee, about ninety miles from Nashville, killing thirty-year-old Cline, Copas, Hawkins, and Hughes instantly. When searchers reached the muddy woods the next morning, they recovered Cline’s wristwatch stopped at the time of impact, less than an hour’s flight from the children she had hurried through the storm to hold.

In early June 1993, before heading out for a string of sold-out shows in Branson, Missouri, Conway Twitty set aside his touring schedule and traveled home to the Mississippi Delta to spend a few quiet days with his eighty-one-year-old mother, Velma Jenkins Dunaway. To the country music world, he was a chart-topping star who had built the sprawling Twitty City complex in Hendersonville, Tennessee, where his mother and extended family had lived beside him for years to make up for their early poverty in Friars Point and Helena. Inside his mother’s home, however, he was still just her eldest son, Harold Lloyd, sitting down for the Southern home cooking he had grown up on. Nothing about that June visit suggested a final goodbye. He talked and laughed with his mother, promised to return soon after finishing his Missouri dates, and stepped back onto the road just as he had done hundreds of times over three decades. On the night of June 4, 1993, Twitty took the stage at the Jim Stafford Theatre in Branson before thousands of fans. Shortly after the show ended, as his tour bus pulled away toward Tennessee, he collapsed from an abdominal aortic aneurysm and was rushed to Cox South Hospital in Springfield. Despite hours of emergency surgery, he passed away early the next morning, June 5, at age fifty-nine. When word reached Velma that morning, the eighty-one-year-old mother was left grieving the healthiest-looking son she had held just days earlier. She lived another sixteen years before passing away in 2009 at age ninety-seven, carrying the memory of that unhurried June visit in the Delta as the last quiet days she ever got with her boy, Harold Lloyd.

When Conway Twitty opened his nine-acre Twitty City complex in Hendersonville, Tennessee, in 1982, he built a private house right next to his own mansion for his mother, Velma. For years, that house stood at the heart of the property alongside homes he built for his four adult children. Having raised young Harold Lloyd Jenkins through lean decades in Mississippi and Arkansas, Velma became a warm, familiar presence on the grounds, often stepping outside to visit with the fans who traveled there to see her son’s work. Whenever Conway came off the road from touring, he could walk across the lawn to check on her, fulfilling a lifelong goal to keep his family close and cared for on the same piece of land. That security vanished after Conway died suddenly from an abdominal aortic aneurysm on June 5, 1993, at age fifty-nine. Because he had not updated his will following his marriage to his fourth wife, Dee Henry, his estate entered a complicated legal dispute between his widow and his four children while facing heavy unpaid debts tied to the complex. To settle the financial obligations and divide the estate under court orders, the entire Twitty City property and his career memorabilia were put up for auction and liquidation in the summer of 1994. That August, eighty-two-year-old Velma had to pack her belongings and leave the home her son had built for her old age. In October 1994, just two months after moving out of the house beside Conway’s mansion, Velma passed away following a rapid decline in her health, unable to outlive the loss of her son and the breakup of the family compound he had built to protect her.

Three days into a desperate search along a swollen, fast-moving river, rescue crews spotted Jack’s horse standing alive beneath an overhanging cliff near the water’s edge. The country singer had vanished while attempting to cross the dangerous current on horseback. For seventy-two hours, local volunteers, authorities, and fellow musicians had combed the jagged canyon walls and downstream bends, fighting harsh weather and rising water in hopes of finding the twenty-nine-year-old artist alive. Away from the stage lights, the horse had been Jack’s closest companion on quiet rides through the backcountry whenever he stepped back from touring to find inspiration. When the search party finally reached the narrow ledge at the base of the rock face, they found the animal soaked, exhausted, and shivering from the cold after pulling itself out of the whirlpools. Its saddle and reins were still clinging to its body, shifted out of place from the struggle in the rapids. The sight of the riderless horse brought the search team to a quiet halt along the riverbank. Having fought its way to solid ground, the animal had refused to leave the stretch of water where its rider had been swept from the saddle, standing for hours beneath the stone overhang and staring out at the muddy current. Rescuers eventually led the surviving horse safely out of the gorge and returned it to Jack’s grieving family. For those who loved him and the men who searched that canyon, the animal coming home alone became both the hardest confirmation of their loss and the last living connection to his final ride.

In 1937, a cheap Sears and Roebuck catalog guitar arrived at a ferryman’s porch in Friars Point, Mississippi, for a four-year-old boy named Harold Lloyd Jenkins. The country was deep in the Great Depression, and the boy’s father, Floyd Jenkins, earned a modest living operating a ferry across the Mississippi River. Saving enough money to order an acoustic instrument through the mail meant trading away practical necessities for a household belief in a toddler’s ear. When Harold sat down with the full-sized guitar, its wooden body nearly hid his small frame, and his fingers could barely reach across the fretboard. Out on the front porch, his grandfather and his father patiently guided his hands through his first chords while steamboat whistles echoed off the water and the Saturday night Grand Ole Opry played through a battery-powered radio. Growing up in the Mississippi Delta, the boy also listened closely to local acoustic blues players and gospel choirs, absorbing the raw vocal grit that would define his adult voice. By age ten, after the family moved across the river to Helena, Arkansas, Harold used those early lessons to form his first band, the Phillips County Ramblers, and host a live Saturday morning show on radio station KFFA. Even when a contract offer from the Philadelphia Phillies and army service in Japan pulled him toward other paths, the habit formed on that oversized Sears guitar brought him back to music. Taking the stage name Conway Twitty, he turned that childhood foundation into a four-decade career with fifty-five Billboard number-one country hits and over sixty-five chart-toppers overall. Through all the years of sold-out arenas and his own Twitty City complex near Nashville, he still credited his ferryman father, his grandfather, and those afternoon lessons on the Friars Point porch for every note that followed.

A polite hello from a former girlfriend on a street in Odessa, Texas broke through Roy Orbison’s quiet composure and inspired his 1961 classic, “Crying.” Raised around the oil fields of Wink and Odessa, Orbison grew up in a West Texas culture that taught men to keep their hurt to themselves. After a painful breakup, he let friends and family believe he had moved on, until he crossed paths with her in town. Shaken by her calm, distant greeting, he went straight to his songwriting partner, Joe Melson. The two turned that moment into a ballad about a man who thinks he is over a breakup until seeing her again brings everything back. In July 1961, Orbison recorded the track at RCA Studio B in Nashville with Monument Records producer Fred Foster, an orchestra, and the Anita Kerr Singers. The melody climbed across two and a half octaves to a soaring final note, forcing engineer Bill Porter to position Orbison at a careful distance on the studio floor so the full force of his voice would not overload the microphone. Released that August, “Crying” sold over a million copies, hitting No. 1 on the Cashbox chart and No. 2 on the Billboard Hot 100 behind Ray Charles’s “Hit the Road Jack.” In an era when male singers were expected to project tough confidence, Orbison stood still behind his dark glasses and let listeners hear a grown man break down. Elvis Presley later called him the greatest singer in the world. After Orbison lost his wife Claudette in a 1966 motorcycle accident and two sons in a 1968 house fire, the song took on an even deeper weight whenever he performed it, including his 1987 duet with k.d. lang. What started with a chance meeting on a Texas street stayed at the center of his music for the rest of his life.

In 1958, Roy Orbison used what little money he had to buy out his contract at Sun Records, trading a label deal for the back seats of parked cars. After his 1956 single “Ooby Dooby” charted, Sun owner Sam Phillips pushed the shy, nearsighted singer in thick glasses to shout and gyrate like Elvis Presley or Jerry Lee Lewis. Refusing to spend his career faking wild rockabilly on stage, Orbison paid his way out of the contract and walked away broke. His young wife, Claudette, was expecting their first child, and relatives urged him to quit music for a steady paycheck in the West Texas oil fields where his father worked. Orbison had studied geology at North Texas State College with that very path in mind, yet he chose to keep driving overnight between Texas and Nashville’s Music Row to pitch songs for Acuff-Rose and send small checks home. With no money for motels, he slept in the back of friends’ cars or on the apartment floor of his songwriting partner, Joe Melson, before smoothing out his suit each morning to audition ballads that executives called too slow for radio. A brief deal at RCA Victor brought more commercial failures, until producer Chet Atkins realized RCA did not know how to use Orbison’s operatic voice and steered him toward Fred Foster at the new independent label Monument Records in 1959. Back home in Odessa, Texas, Orbison and Melson sat for hours inside a car parked at the curb, building orchestral ballads around his natural range. After Elvis Presley and the Everly Brothers both turned down their new song, “Only the Lonely,” Foster let Orbison record it his own way with strings in the spring of 1960. The record reached No. 2 in the United States and No. 1 in Britain, proving that the quiet Texan standing still behind the microphone never needed to imitate anyone else.

On February 22, 1968, Johnny Cash stopped his band in the middle of a song in London, Ontario, refusing to play on until June Carter agreed to marry him. Cash had been asking since they first met backstage at the Grand Ole Opry in 1956. Over the next twelve years, he proposed at least 30 times, and Carter always said no. When his addiction to pills and alcohol nearly killed him, Carter and her parents moved into his home, took away his drugs, and stayed up through the nights to watch over him, though she refused to become his wife until he got clean. By early 1968, Cash had turned his life around, recording his live album at Folsom Prison in January with Carter singing beside him. A month later in Canada, he carried a diamond ring in his suit pocket for days, waiting for a moment where she could not dodge the question or slip backstage. At the London Gardens arena, in front of 7,000 fans, he stopped their Grammy-winning duet “Jackson” and pulled out the ring. Carter had grown up performing with her family and knew how to handle any crowd, yet she blushed, clasped her hands together, and tugged at his coat sleeve, urging him to keep singing. Cash waited at the microphone while 7,000 people cheered for an answer. After she finally said yes, the two held hands backstage and decided to fly to the Bahamas the very next day. One week later, on March 1, 1968, they married at a church in Franklin, Kentucky. They stayed together on the road and at home for 35 years, until Carter passed away in May 2003 and Cash died four months later.

In 2003, Toby Keith stepped onto Willie Nelson’s tour bus in Las Vegas to celebrate their number one duet and ended up missing his flight the next morning. That week, “Beer for My Horses” was in the middle of a six-week run atop the Billboard Hot Country Songs chart. The two had gathered in Vegas for the Academy of Country Music Awards and a television special marking Nelson’s 70th birthday. After the show, Nelson invited his younger singing partner aboard his famed bus, Honeysuckle Rose. Standing over six feet tall, Keith carried the reputation of a burly Oklahoma powerhouse who could hold his own anywhere. He had actually quit smoking years earlier to keep up with his work schedule, yet nobody in country music said no when Willie Nelson offered to share on his own bus. It took very little to knock the younger star flat. Dizzy and overwhelmed, Keith made his way back to his room at the Mirage, slept for hours, and missed his plane the following day. Once he woke up aboard his own bus, Big Dog Daddy, he told the whole story to his longtime guitarist and co-writer Scotty Emerick. Laughing at the misadventure, the pair grabbed acoustic guitars and wrote “I’ll Never Smoke Weed with Willie Again.” Before releasing it, Keith played the demo for Nelson to make sure the joke landed right. Nelson laughed until tears came to his eyes and gave his full blessing. Keith included the recording as a hidden bonus track on his November 2003 album Shock’n Y’all, and fans requested it at his shows for the next twenty years. Even after Keith passed away in February 2024, that night in Vegas stayed with listeners as a favorite memory of a superstar who never minded making himself the punchline alongside his hero.