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Greatest Hits Oldies But Goodies Ever

Four friends walked onto the stage as The Highwaymen in 1985, and by the autumn of 2024, 91-year-old Willie Nelson was the only one left to carry their songs alone. When Willie Nelson, Johnny Cash, Waylon Jennings, and Kris Kristofferson first joined forces in the mid-1980s, they stood shoulder to shoulder in a single line across the stage. Over the next four decades, that line slowly disappeared. Waylon Jennings passed away first on February 13, 2002, at age 64 after years of diabetes complications. Less than 19 months later, after losing his wife June Carter in May 2003, Johnny Cash spent his final months nearly blind and in a wheelchair in Hendersonville while Willie kept calling to check on him. When Cash died on September 12, 2003, at age 71, Willie went to the Ryman Auditorium that November to sing his friend home. For the next twenty years, only Willie and Kris Kristofferson remained. As severe memory loss from chronic Lyme disease forced Kristofferson into retirement in 2021, Willie refused to let him fade away. At Willie’s 90th birthday concert at the Hollywood Bowl in 2023, he brought Kris out, stood close beside him, and gently guided the rhythm so his old friend could still share the microphone with dignity. On September 28, 2024, Kristofferson died peacefully at his home in Maui at age 88. Days later, Willie walked back onto the stage with Trigger, the same battered acoustic guitar that had been in those 1980s recording rooms with all four men. Instead of stepping back in grief, he played a song Kristofferson had written, keeping the voices of Waylon, Johnny, and Kris alive inside his own setlist.

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When Kris Kristofferson died at his home in Maui on September 28, 2024, at the age of 88, 91-year-old Willie Nelson became the last living member of The Highwaymen, yet he did not cancel a single show.

Instead, Willie stayed out on the Outlaw Music Festival Tour with Trigger strapped across his shoulder. Only days after losing his final partner from the legendary quartet, he sat before thousands of fans and opened his set with the songs they had shared for forty years.

That brotherhood came together almost by accident in late 1984 in Montreux, Switzerland, where Johnny Cash was filming a Christmas television special. Willie, Waylon Jennings, and Kristofferson had flown in to join him, and between camera setups, the four men spent their evenings trading guitars and old stories in their hotel rooms.

Back in Nashville, producer Chips Moman brought them into Moman’s Recording Studio to capture that informal energy on tape. During those sessions, songwriter Jimmy Webb sent over an unfinished cassette of a track about souls returning across centuries, and that recording gave the group both its signature hit and its permanent name in May 1985.

Although they did not adopt the formal name The Highwaymen until years later, the debut album reached number one on the country charts and turned four individual stars into a touring institution. Between 1985 and 1995, they recorded three studio albums, finishing with The Road Goes On Forever under producer Don Was, and took their three-hour shows to arenas from the Nassau Coliseum in New York to festivals in Europe.

On stage, they stood in a straight line across the front of the bandstand, trading verses without choreography or ego. Behind the scenes, the road was already testing their health, as Waylon fought through bypass surgery and worsening diabetes while Johnny dealt with chronic pain and autonomic neuropathy.

Waylon was the first to leave that line when he died in Chandler, Arizona, on February 13, 2002, at age 64. Willie traveled to Mesa for the private service and immediately folded Waylon’s outlaw anthems permanently into his own nightly repertoire so the crowd could still sing them back.

Nineteen months later, the loss doubled. After June Carter Cash died in May 2003, Johnny spent his final summer in Hendersonville, Tennessee, nearly blind and confined to a wheelchair, while Willie called regularly from his tour bus just to check on his friend.

Johnny died on September 12, 2003, at age 71. That November, Willie walked onto the stage of the Ryman Auditorium for the public memorial broadcast and sang the songs they had traded back in Switzerland nearly two decades earlier.

For the next twenty-one years, only Willie and Kristofferson were left to carry the history of the quartet. When severe memory loss, which doctors eventually traced to chronic Lyme disease after years of misdiagnosis, forced Kris to retire in early 2021, Willie made sure his friend was never forgotten by the public.

At Willie’s 90th birthday concerts at the Hollywood Bowl in April 2023, Kris walked out as a surprise guest to perform a duet with Rosanne Cash. Watching from nearby, Willie stayed close to his old bandmate, lending quiet support as the Los Angeles crowd rose to give Kristofferson one final ovation.

When word arrived from Hawaii in the autumn of 2024 that Kris had passed away surrounded by his family, Willie answered the only way he ever had. At upcoming tour stops in Texas and across the South, he leaned into the microphone and dedicated his traditional closing medley of Kristofferson’s classic gospel and Sunday-morning compositions to the man who wrote them.

He also kept the enduring duets he had recorded with Waylon and the opening tributes to Johnny right where they had been in his setlist for twenty years. At 91, seated on a stool behind the worn cedar top of Trigger, Willie often pointed toward the crowd and let the audience sing the verses his three friends used to handle.

Four voices once filled the front of that stage in 1985, and for as long as Willie’s tour bus keeps rolling down the highway, one battered guitar is still making room for all of them.

https://youtu.be/dBN86y30Ufc?si=a_wQtKtEh1qaYCiu

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When a July 2022 cycling accident left Amy Grant unable to recall songs she had sung for forty years, Vince Gill cleared his schedule to help her start over. The fall happened on July 27 at Nashville’s Percy Warner Park after her bicycle wheel hit a pothole, leaving her unconscious for ten minutes despite her helmet. She spent two nights at Vanderbilt University Medical Center with a traumatic brain injury, just two years after undergoing open-heart surgery in June 2020 for a congenital defect. Back home, the lingering effects of the concussion took hold. Sensitivity to light and noise kept her in a quiet room with the curtains drawn, while balance issues forced an avid walker to move one slow step at a time. Worse still, short-term memory loss erased family stories, the names of longtime colleagues, and the words to songs from her four-decade career. Vince immediately postponed her fall tour and canceled his own upcoming performances, turning off electronics and limiting visitors at their Nashville house. Every afternoon, he walked beside her with an arm around her waist to steady her down the hallway and along the garden path. When she cried in the dark and asked if this was all she had left, he held her and promised to do the remembering for her while she began writing daily notes in a journal. By November and December 2022, she was ready to attend the Kennedy Center Honors and join him for their annual Christmas at the Ryman residency. Vince placed large notebooks and a teleprompter in front of her onstage, staying close enough to rest a hand on her shoulder and cover any brief pause with gentle humor until she found her next line.

In 1975, while country radio was filled with songs about barroom infidelity and broken marriages, Don Reid wrote a ballad about keeping a wedding vow until the end of life. Released as a single from The Statler Brothers’ album The Holy Bible: Old Testament, “I’ll Go to My Grave Loving You” climbed to number three on the Billboard Hot Country Singles chart and became one of the quartet’s biggest records of the 1970s. Don drew the song from his own marriage to his high school sweetheart, Brenda, back home in Staunton, Virginia. With his older brother Harold anchoring the bass and Phil Balsley and Lew DeWitt completing the four-part harmony, the record sounded less like a stage performance and more like a quiet promise made in a living room. Eighteen years later, the brothers returned to that same theme from the other side of middle age. By 1993, as the group members entered their fifties and sixties, Don and Harold Reid sat down together to write “I’ve Never Lived This Long Before” for their album Home. Backed by Phil Balsley and tenor Jimmy Fortune over a sparse, unhurried arrangement, the two men traded their usual stage humor for an honest look at graying hair and the quiet surprise of growing old. Where the 1975 hit carried the steady voice of a young husband looking ahead, the 1993 recording sounded like two longtime partners talking across the dinner table after decades together. Rather than chasing a younger crowd in the 1990s, The Statler Brothers chose to age right alongside the people who bought their records. Those two songs, recorded eighteen years apart, went on to be played at countless silver and golden wedding anniversaries and funeral services across America, giving couples the words for both the promise of youth and the gratitude of old age.

Long before Conway Twitty earned 40 number one singles on the Billboard country charts, an elderly Black neighbor in the Mississippi Delta taught a six-year-old white boy how to play the blues on a cheap Sears & Roebuck toy guitar. Born Harold Lloyd Jenkins on September 1, 1933, he grew up during the Great Depression in Friars Point, Mississippi. His parents, Mississippi River ferryboat captain Floyd Jenkins and his wife Velma, raised their family among one of the few white households in a community of Black cotton pickers and sharecroppers. When Harold’s grandfather, Papaw McGinnis, ordered him a mail-order guitar with stiff steel strings around age four or five, the boy took it next door to an older neighbor he respectfully called Uncle Fred. After long days working in the cotton fields, Uncle Fred sat on his wooden porch with an old guitar and a harmonica, showing the boy how to press the strings without hurting his fingers and how to slide a glass bottleneck or pocketknife blade along the neck. Even under the strict racial segregation of the Jim Crow South in the late 1930s, Floyd and Velma Jenkins encouraged their son to learn from Uncle Fred and treat him like family. On Sunday nights, the Jenkins family stood outside the open windows of the local Black church to listen to the gospel choir, while young Harold also absorbed the rhythms drifting from nearby juke joints. When the family moved across the river to Helena, Arkansas, in 1943, the ten-year-old carried those Delta blues and gospel lessons into his first band, the Phillips County Ramblers. Decades later, whenever interviewers asked where he found the low vocal growl and phrasing that carried him from 1950s rockabilly to the top of country radio, Twitty pointed back to Uncle Fred on that wooden porch in Friars Point.

On October 12, 1991, over 2.2 million American households tuned in at 9 p.m. to watch four men in tailored suits sing gospel and country harmonies, breaking the all-time premiere record for The Nashville Network. By the early 1990s, commercial country music was rapidly chasing younger crowds with pyrotechnics and arena rock production. Harold Reid, Don Reid, Phil Balsley, and Jimmy Fortune went the opposite direction. Stepping onto the stage just over a year after losing founding tenor Lew DeWitt in August 1990, the quartet built The Statler Brothers Show around the classic variety format they grew up loving. For seven seasons and more than 150 episodes, the formula never changed. The four men stood close together at the microphones, traded clean Vaudeville-style comedy sketches featuring Harold as Lester “Roadhog” Moran, and closed every single Saturday night broadcast with a solemn gospel hymn. Three generations of families could sit in the same living room without ever reaching for the remote. While mainstream country radio was quietly pushing older pioneers off the airwaves, the Statlers used their top-rated stage to welcome them home. They gave a place of honor in their first season to Johnny Cash, the mentor who had carried them on tour for over eight years early in their career, and regularly hosted veterans like Loretta Lynn, George Jones, Conway Twitty, and Roy Rogers. The show remained the number-one program on the entire network until its final broadcast in May 1998, ending only because new corporate owners wanted a younger demographic. After each taping in Nashville, all four men still packed their bags and drove straight back to their families and local churches in Staunton, Virginia, leaving behind a seven-year television run that proved old-fashioned grace never actually lost its audience.

In February 1979, five years after Dolly Parton wrote “I Will Always Love You” to say goodbye to Porter Wagoner, her former mentor sued her for $3 million, and years later she still stepped in to save him from losing everything. When Parton left The Porter Wagoner Show in 1974, their careers moved in opposite directions. She crossed into pop music with her 1977 hit “Here You Come Again,” won the 1978 CMA Entertainer of the Year award, and prepared to film “9 to 5” in Hollywood, while Wagoner faced stalling sales and financial trouble. In his 1979 federal lawsuit in Nashville, Wagoner demanded 15 percent of Parton’s future earnings and claimed co-ownership of Owe-Par, the publishing company she had founded at age 21 with her uncle Bill Owens to protect the hundreds of songs she wrote between 1967 and 1974. While smiling on the “9 to 5” film set by day, Parton spent months dealing through lawyers with the man who had once defended her against booing audiences in 1967. In 1980, she agreed to pay Wagoner $1 million in installments out of her studio, touring, and film income to settle the suit and keep full ownership of her songwriting catalog. Seven years later, Parton ended the silence by inviting Wagoner onto her 1987 television show, where they embraced on stage. When severe IRS debt threatened to wipe Wagoner out in the late 1980s, Parton bought the rights to their shared duet catalog to help him clear his debts, then returned those rights to him once he recovered financially. In 2007, Parton sat by Wagoner’s hospital bed and held his hand shortly before he passed away, having long since forgiven the lawsuit between two proud partners who had shaped each other’s lives.

In February 2021, Tennessee lawmakers from both political parties united to place a statue of Dolly Parton on the State Capitol grounds, and she wrote a letter asking them to stop. Weeks earlier, State Representative John Mark Windle had introduced House Bill 0136 to honor Parton in Nashville for everything she had given the state. Even though the monument would be funded through private donations rather than taxpayer money, the bill was moving easily toward approval when Parton stepped in on February 18, 2021. Given everything the world was enduring during the height of the COVID-19 pandemic, she told the legislature that she did not think putting her on a pedestal was appropriate at that time. While thousands of families were grieving and struggling to buy food and medicine, she did not want private funds or public attention spent casting her likeness in metal. Months before turning down the monument, Parton had donated $1 million to Vanderbilt University Medical Center in Nashville to help fund early research for the Moderna COVID-19 vaccine. The gift grew out of her friendship with Dr. Naji Abumrad, who had treated her after a minor 2013 car accident, and Parton was surprised when her name later appeared in the New England Journal of Medicine. She always cherished the modest 1987 bronze statue on the courthouse lawn in her hometown of Sevierville, yet she repeatedly stepped back from grander honors, twice declining the Presidential Medal of Freedom while her husband was ill and initially asking to withdraw from the 2022 Rock & Roll Hall of Fame ballot. To soften the refusal for Nashville lawmakers, Parton ended her 2021 letter by joking that if they still felt she deserved a Capitol statue several years down the road or after she was gone, she would proudly stand there as a grateful Tennessee citizen.

On August 26, 2026, the clock tower at the Sevier County Courthouse rang for five straight minutes to say goodbye to a local farmer’s daughter who once walked past those steps barefoot. One day after Dolly Parton’s passing, Sevier County officials held an official hometown memorial in the center of Sevierville, Tennessee. As the historic bells echoed toward the Great Smoky Mountains, thousands of residents, visitors, and county leaders gathered on the courthouse lawn. When the final chime faded, the entire town entered five minutes of silence. Along the Parkway and the streets surrounding the square, drivers pulled over, turned off their engines, and stepped out with their hats in their hands. Nearby shopkeepers paused their work and stood in the doorways. The crowd gathered around the bronze statue of a young Dolly holding a guitar, sculpted by Jim Gray and placed on the lawn in May 1987. Parton often said that hometown tribute meant more to her than any Grammy or Hollywood award, and she loved telling how her father, Lee Parton, used to sneak out at night with a bucket of soapy water and a broom to scrub bird droppings off the bronze himself. In the 1950s, the fourth child of Lee and Avie Lee Parton rode into town from Locust Ridge in a worn-out truck, wearing patched clothes past that same courthouse. Decades later, her Dollywood park, Buddy Program scholarships, hospital funding, wildfire relief, and Imagination Library had created tens of thousands of jobs and supported generations across East Tennessee. At the base of the stone pedestal, former 1964 Sevier County High School classmates and young children who grew up receiving her monthly books left mountain wildflowers, small guitars, paper butterflies, and children’s storybooks on the grass where her father once stood with his bucket and broom.

For seven years, audiences watching Dolly Parton and Porter Wagoner sing together were convinced they were secret lovers, while her husband Carl Dean quietly trusted her from their Nashville farm. When Dolly joined The Porter Wagoner Show in September 1967 at age 21, Porter was separated from his second wife, Ruth Olive Williams, and newly split from former singing partner Norma Jean. Dolly had been married for over a year to Carl Dean, an asphalt paving businessman she wed on May 30, 1966, in Ringgold, Georgia. After attending one BMI awards dinner in a tuxedo in 1966, Carl told Dolly he loved her rather than her industry and stayed home, never letting gossip cross their threshold. Between 1967 and 1974, Porter and Dolly recorded 13 studio albums together and won CMA Vocal Duo of the Year in 1968, 1970, and 1971. The way they held hands and looked at each other during songs like “Holding On to Nothin’,” “Just Someone I Used to Know,” and “Please Don’t Stop Loving Me” left millions of viewers and Nashville reporters certain they were hiding a romance. Both maintained their bond was never physical. Behind the curtain, Dolly was one of the few people willing to argue with Porter over every note and arrangement, and that stubborn friction gave their stage performances an unusual charge. On the Wagon Masters tour bus, she kept clear boundaries, spending her spare hours writing songs alone or calling Carl. Porter later admitted that he loved Dolly deeply, mixing a mentor’s pride with the bond of seven years side by side, though he knew her heart belonged to her husband and her own music. In October 2007, long after their 1970s legal battles had faded and hours before Porter died of lung cancer at age 80, Dolly stood by his hospital bed, held his hand, and softly sang to him one last time.

For six years, millions of television viewers knew her as Pretty Miss Norma Jean, while behind the curtain she was trapped in a secret relationship with Porter Wagoner. Norma Jean Beasler joined The Porter Wagoner Show in 1961 at age 23 and quickly became a favorite in American living rooms. Off camera, she entered a six-year romance with Porter, who remained married to his second wife, Ruth Olive Williams, and had three children at home. Afraid of ruining his family-friendly television image, Porter never kept his promises to end his marriage. Instead, he dictated her wardrobe, her song list, and her personal life. Traveling as the only woman on a tour bus with the all-male Wagon Masters band, she was barred from talking freely with anyone outside the troupe. At RCA Victor, Porter stood in the studio supervising her sessions while she recorded hits like “Go Cat Go” and country ballads about betrayal and waiting in vain. Guilt and isolation pushed her into depression, and she began drinking heavily alone in hotel rooms after shows. The breaking point arrived during a tour stop in Atlanta, when a fierce argument over their relationship turned physical in a hotel room and put Norma Jean in the hospital. That night ended her hopes for a future with him. In 1967, at the height of her popularity and with a Grammy nomination to her name, she quit the show, vacating the spot soon filled by a young Dolly Parton. That September, Norma Jean married singer Jody Taylor, wanting simply to walk beside a husband in daylight, and retreated to a quieter life in Oklahoma. Though old emotional scars lingered into that marriage, Norma Jean said in her later years that leaving Porter’s show in 1967 was the decision that saved her life before alcohol and despair could destroy her.