OldiesSong

Greatest Hits Oldies But Goodies Ever

During The Highwaymen’s March 1990 tour stop at New York’s Nassau Coliseum, Willie Nelson and Kris Kristofferson quietly adjusted the show onstage whenever Johnny Cash or Waylon Jennings began running out of breath. To the 16,000 fans in the arena, the four stars promoting their album Highwaymen 2 still looked like the untamed rebels of the 1970s. Behind the curtain, they were men in their fifties and sixties carrying heavy physical wear. Jennings was fighting diabetes and recovering from triple-bypass heart surgery in December 1988, while the 58-year-old Cash was dealing with chronic pain, heart and blood pressure trouble, and a strained voice. Their history went back to the 1960s, when Cash and Jennings shared a small Nashville apartment and Kristofferson swept studio floors while trying to get his songs heard. By 1990, the wild all-night parties were gone. Before each show, the four friends sat around a dressing room table with cups of warm water, talking about their kids and checking on each other’s breathing and energy for the night ahead. Once the lights came up, Nelson kept a close eye on Cash and Jennings while playing his guitar, Trigger. Whenever Jennings winced or Cash labored for air, Nelson and Kristofferson stepped forward to draw the crowd’s focus, signaling the band to stretch out a guitar solo, thickening their vocal harmonies, or adding to their own sets so their brothers could rest without losing their pride in front of the audience. That March 1990 concert was filmed and later released as The Highwaymen Live: American Outlaws, capturing one of the last great peaks of all four men standing side by side before Jennings passed away in 2002 and Cash followed in 2003. The crowd in New York heard four outlaws in full command, never realizing how much of that night was held together by two friends covering for the other two in plain sight.

Please scroll down for the video. It is at the end of the article!

On March 14, 1990, Johnny Cash, Waylon Jennings, Willie Nelson, and Kris Kristofferson walked out before 16,000 fans at Nassau Veterans Memorial Coliseum in Uniondale, New York. While the two-and-a-half-hour concert was recorded as a showcase for their newly released album Highwayman 2, the night required Nelson and Kristofferson to quietly pace the stage so their two older bandmates could make it through the set.

Only fifteen months earlier, both Jennings and Cash had been patients at Baptist Hospital in Nashville during the same week in December 1988. Jennings underwent triple-bypass heart surgery on December 12 after forty years of heavy smoking, and seven days later, the 56-year-old Cash was admitted for double coronary artery bypass surgery.

By March 1989, the four friends had regrouped with producer Chips Moman at Emerald Sound Studio in Nashville, Three Alarm Recording Studio in Memphis, and Nelson’s Pedernales studio in Spicewood, Texas, to cut Highwayman 2. Released by Columbia Records in February 1990, the album reached No. 4 on the country chart and sent the quartet onto a multi-city arena tour.

Their bond stretched back to the 1960s, when Cash and Jennings shared an apartment in Nashville and Kristofferson worked as a janitor at Columbia Recording Studios while trying to pitch his songs. Two decades later, the backstage routine looked very different from their early years on the road.

Before going onstage in 1990, the four men sat together around a dressing room table with cups of warm water, talking about their children and checking on each other’s breathing and stamina. Jennings, then 52, was managing diabetes alongside his heart recovery, while the 58-year-old Cash was contending with chronic pain, blood pressure issues, and a fatigued voice.

The Nassau Coliseum setlist spanned more than thirty songs, opening with “Highwayman” and moving through “Mammas Don’t Let Your Babies Grow Up to Be Cowboys,” “Folsom Prison Blues,” “Always on My Mind,” and “Me and Bobby McGee”. Trading verses across a marathon show demanded constant physical adjustments under the arena lights.

Playing his battered acoustic guitar, Trigger, the 56-year-old Nelson kept watch over Cash and Jennings throughout the performance. Whenever Jennings showed signs of discomfort or Cash began running short of breath, Nelson and the 53-year-old Kristofferson stepped toward the front of the stage to pull the audience’s attention.

Without breaking the flow of the concert, Nelson signaled the band to stretch out instrumental solos, while he and Kristofferson thickened the vocal harmonies or extended their own turns at the microphone. Those small shifts gave Cash and Jennings time to catch their breath in plain sight without sacrificing their pride in front of the New York crowd.

First issued in an abbreviated video release in 1991 and later restored in full in 2016 as The Highwaymen Live: American Outlaws, the Long Island concert captured the group on one of its final major arena runs. They continued touring intermittently, filming a show in Aberdeen, Scotland, in 1992 before gathering at Ocean Way Recording in Hollywood in late 1994 with producer Don Was.

Those California sessions produced their third and final studio album, The Road Goes On Forever, released in April 1995. A supporting tour carried the four friends through North America, Australia, and New Zealand later that year, even as circulatory problems and diabetic nerve pain made travel increasingly difficult for Jennings.

After their final full-group appearances in the mid-1990s, Jennings curtailed his road schedule in 2000 and passed away from diabetic complications on February 13, 2002, at age 64. Cash died nineteen months later on September 12, 2003, at age 71, and Kristofferson remained close with Nelson for another two decades until his death on September 28, 2024, at age 88, leaving Nelson as the last surviving member.

In his autobiography, Jennings looked back on the four of them standing together around the microphones and wrote that there were no other four people like them. At Nassau Coliseum in March 1990, the 16,000 people in the seats heard four country outlaws in full voice, carried through the night by two friends watching the other two from a few feet away.

https://www.youtube.com/watch?v=bMdeg-WKt1U

Related Post

In May 1981, while stepping off his tour bus during a long road stretch, Conway Twitty slipped and fell backward, striking his head against the metal steps and the ground until he lost consciousness. Emergency care saved his life and left his mobility intact, allowing him to return quickly to the stage to perform his hit Tight Fittin’ Jeans. In 1981, medical awareness of how closed head injuries could alter personality was still limited, and fans who saw him singing smoothly assumed he had fully recovered. Only his family and the members of his band, the Twitty Birds, saw the neurological toll that followed, as the patient, gentle husband known at home as Harold Jenkins grew uncharacteristically distant, irritable, and depressed. For his wife, Temple “Mickey” Medley Jenkins, who had stood by him since 1956, the hardest part was not the physical recovery. It was watching the affectionate man she had loved for twenty-five years become a stranger under their own roof, subject to sudden anger and impulsive decisions he never would have made before the fall. Already worn down from more than two decades of raising their children largely alone while her husband toured over 200 days a year, Mickey now managed the sprawling nine-acre Twitty City complex that opened in 1982 in Hendersonville, Tennessee, to house their extended family. Inside that dream estate, she absorbed his mood swings in silence, never once speaking to the press so the public could keep its image of the polished country gentleman. Although Mickey held the household together for several more years, the lingering change from that 1981 accident eventually strained their 36-year marriage to a late-1980s divorce. Years after his passing in 1993, their children, including Joni and Jimmy Jenkins, still remembered how that fall on the tour bus steps took away part of their father’s warm spirit, and how their mother quietly carried the family through the darkest years behind the scenes.

In 1989, Randy Owen turned his living room in Fort Payne, Alabama, into a makeshift call center that went on to raise more than $800 million for St. Jude Children’s Research Hospital. That effort began when St. Jude founder Danny Thomas asked the Alabama frontman to rally country radio and its listeners around children fighting life-threatening illnesses. Having grown up poor on a cotton farm on Lookout Mountain, Owen knew the fear working families faced when medical bills arrived, and St. Jude’s rule that no family ever pays for treatment, travel, housing, or food struck a personal chord. At the peak of Alabama’s career, Owen did not simply write a check and hand the project to staff. He, his wife Kelly, and their three children, Alison, Heath, and Randa, sat around their farmhouse telephone calling station directors across the country and mailing out letters by hand to launch Country Cares for St. Jude Kids. When Danny Thomas died in early 1991, Owen treated that 1989 request as a lifelong promise. What started with a few dozen stations grew into an annual network of more than 200 country radio outlets and Generations of Nashville stars, powered largely by truck drivers, farmers, and factory workers pledging $15 or $20 a month. Over three decades, Owen kept visiting the halls in Memphis without cameras around, learning children’s names and holding exhausted parents. The hardest moments came when he returned the following year to find a familiar bed empty, a loss that kept him coming back to the phone lines. St. Jude later honored him with the Michael F. Tamer Award and named a memorial garden and patient lobby for the Owen family. Those farmhouse calls in Fort Payne helped ensure thousands of parents walked through the hospital doors without ever seeing a bill.

When fans across America in the 1970s assumed Conway Twitty and Loretta Lynn were secret lovers, Conway’s wife Mickey responded by welcoming Loretta as a close family friend. Starting in 1971, Conway and Loretta recorded a string of dramatic duets including After the Fire Is Gone, Lead Me On, and Louisiana Woman, Mississippi Man, winning four straight CMA Vocal Duo of the Year awards from 1972 to 1975. Because their songs often dealt with temptation and unfaithful hearts, and the pair sang holding hands while looking straight into each other’s eyes on television, viewers and the press constantly whispered about an offstage romance. Temple “Mickey” Medley Jenkins had married Conway in 1956 when he was still an unknown singer named Harold Jenkins, and together they raised three children, Joni, Kathy, and Jimmy. Instead of letting the gossip or her husband’s image as a matinee idol rattle her, Mickey trusted his character and treated those intense stage moments as honest work that supported their family. Both Mickey and Loretta, who came from humble Kentucky coal country, were hardworking Southern wives and mothers. Backstage and on tour buses, the two women spent hours talking about recipes, children, and home life. Conway also built a genuine brotherhood with Loretta’s famously fiery, jealous husband, Oliver “Doolittle” Lynn, putting any suspicions to rest inside both marriages. Whenever reporters pressed Loretta about a secret affair, she laughed and told them she loved Mickey, Doolittle got along well with Conway, and their closeness offstage made acting out love songs effortless. In Tennessee, where the families visited each other at home in Hendersonville and Conway’s children grew up treating Loretta like an aunt, Mickey’s steady grace across 36 years of marriage gave the duo the peace of mind to record five consecutive number-one hits and eleven studio albums.

When Hank Williams Jr. turned 18 in 1967, his fiercely protective mother trusted only one musician in Nashville to take him out on the road, Waylon Jennings. Since age eight, Hank Jr. had been sent onstage in suits and cowboy hats like his father’s to sing the late star’s catalog. His mother, Audrey Williams, controlled his career tightly because Hank Williams Sr. had died in the back seat of a car on tour at age 29, and she feared the road would take her only son the same way. Jennings, then around 30, knew how fragile a musician’s life could be after giving up his seat on the 1959 flight that killed Buddy Holly. Though Nashville saw him as a rebel, he kept his word to Audrey. Riding the tour bus with Jennings and The Waylors gave the teenager his first freedom away from home under the eye of an older brother who knew where to draw the line. On that bus, he was treated as Bocephus rather than a copy of his father. During long drives between states, Jennings told him plainly that he could not spend his life imitating a ghost and pushed him to find his own music. That push helped Hank Jr. leave the tribute act behind in the 1970s and build his own style of Southern rock and outlaw country. When a 1975 fall down Ajax Peak in Montana nearly cost him his life, Jennings stood by him during recovery and produced the music that helped bring him back. The trust Audrey placed in Jennings in 1967 turned into a lifelong brotherhood, giving a teenager in his father’s clothes the room to become his own man.

On May 6, 2006, while her debut album was selling millions across America, Carrie Underwood put on a green cap and gown to graduate from college in Tahlequah, Oklahoma. Education came first in her home long before music became a career. Her mother, Carole, taught sixth grade in Checotah for 25 years, including one year with Carrie in her own classroom. Carrie grew up watching her mother stay up late at the kitchen table grading papers after long days at school. After graduating as salutatorian of Checotah High School in 2001, Underwood studied broadcast journalism at Northeastern State University so she would have a steady job if singing fell through. In the fall of 2004, just one semester short of her degree, she auditioned for American Idol and won the competition in May 2005. Her debut album, Some Hearts, soon sold millions of copies and put her on a heavy North American tour schedule. Still, she had promised her mother she would graduate and refused to waste nearly four years of classes. To complete her final three internship credits, the university let her study television production backstage during her tour and at American Idol tapings, turning in written reports between shows. When commencement arrived in May 2006, Underwood turned down special arrangements for celebrities. She lined up alphabetically with more than 1,300 students, sat with her classmates, and walked the stage to receive her degree in mass communication magna cum laude. Her parents, Stephen and Carole, watched from the audience as she finished what she had started before the fame. For a Checotah teacher who had spent a quarter century in the classroom, that diploma mattered every bit as much as the platinum records already hanging on her daughter’s wall.

In the crowded wings of Nashville’s Ryman Auditorium on January 14, 1967, Rozene Pride squeezed her husband Charley’s hand before he walked out onto the Grand Ole Opry stage. To get past racial bias, RCA Victor had mailed his first three singles to radio stations without publicity photos until his third release, Just Between You and Me, cracked the country top ten and earned a Grammy nomination in late 1966. Stepping onto the Ryman stage that Saturday night made him the first Black performer on the Opry since harmonica player DeFord Bailey in 1941. At an earlier 1966 concert in Detroit, ten thousand people had fallen dead silent for twenty seconds when they saw his skin color. Amid the tensions of 1967, the couple knew the real test was how a Southern auditorium would react to seeing the face behind the radio voice. Growing up picking cotton in Sledge, Mississippi, and later working at a Montana lead smelter in the early years of their marriage, Charley had listened to Saturday night Opry broadcasts on WSM radio. Dressed with quiet elegance in a backstage area where a Black headliner and his wife were an unfamiliar sight, Rozene stood tall and held his hand until his nerves settled. Traditional country legend Ernest Tubb stepped to the microphone first, giving the newcomer a warm introduction before the Ryman crowd and millions of WSM radio listeners. Once Charley began singing in the familiar baritone fans had played for months, accompanied by the cry of the pedal steel guitar, the auditorium broke into thunderous applause and rose to its feet. Watching from the wings as the crowd swayed to his voice, Rozene knew the hardest door in Nashville had finally opened for their family. Twenty-six years later, when Charley was officially inducted as a member of the Grand Ole Opry in May 1993, Rozene was still standing right beside him backstage.

In 1970, rather than staging a celebrity wedding in Nashville or Texas, 45-year-old Hank Thompson married Ann Williams quietly in her home state of Michigan without a single reporter present. By then, the Western swing star was a millionaire who had dominated the country charts for over two decades, sold tens of millions of records, and performed under bright lights in custom rhinestone Nudie suits worth thousands of dollars. Behind the scenes, a wartime breakup in 1945 and the sudden collapse of his first marriage to Dorothy Jean Ray in 1951 had kept him single for 19 years. Meeting Ann in Michigan during the late 1960s had finally ended that long solitude, and at 45, Thompson knew a loud spectacle had nothing to do with a lasting home. Holding the wedding in her northern hometown honored the place where they first met while shielding a grounded, private woman from the glare of the entertainment press. Leaving his flashy stage persona behind, Thompson exchanged vows in front of only their closest family members and a handful of dear friends. For the veteran musicians in his band, the Brazos Valley Boys, who had watched him walk back into lonely hotel rooms after shows for nearly two decades, the day brought deep relief that their bandleader had found a true partner. While many honky-tonk stars of his era went through three, four, or five publicized marriages in the tabloids, those quiet vows in Michigan began a steady life together in Texas. The promise made in that small room without flashing cameras lasted 37 years until November 2007, when Thompson took his final breath in Ann’s arms at their home in Keller.

In 1997, Capitol Records prepared a recording contract for Carrie Underwood at age 14, then canceled the offer after a sudden change in company leadership. Until then, she had sung mostly in church and at local festivals around Checotah, Oklahoma. Her father, Stephen, worked at a paper mill and tended the family farm, while her mother, Carole, taught elementary school. When a local contact arranged a Nashville audition, that trip was paid for through her parents’ steady working wages. Her audition convinced the staff at Capitol Records, and the family went home waiting for the final paperwork. Before the contract was ever signed, a management shakeup inside the label wiped out the deal. Rather than staying in Nashville to knock on other doors, Underwood returned to Checotah and focused on school. For the next eight years, she lived a normal life in Oklahoma. She graduated as salutatorian of Checotah High School in 2001, studied mass communication at Northeastern State University, and worked shifts at a pizzeria and a veterinary clinic. By age 21, she believed her music dream was behind her and planned to pursue a career in television news after graduation. An audition for the fourth season of American Idol in 2004 changed that plan. When she won the title in 2005 at age 22, the label that signed her and released her platinum records was Capitol Records Nashville, the very company that had turned her away eight years earlier. Underwood later called that canceled 1997 deal a blessing in disguise, admitting she had not been ready at 14 for the pressures of the business. Those eight ordinary years in Oklahoma gave her the grounding to handle stardom when the same door opened a second time.

Backstage at the CMA Awards in Nashville on November 11, 2020, 86-year-old Charley Pride spent his final press interview bragging about how beautiful his wife Rozene was. Moments earlier inside the Music City Center, he had performed with Jimmie Allen and accepted the Willie Nelson Lifetime Achievement Award. Looking out at the socially distanced tables where Rozene sat in her eighties with her familiar grace, he held the trophy and thanked his “special Rozene” for keeping him steady through 64 years of marriage. When reporters in the press room afterward asked about their six decades together, Charley’s face lit up with a memory from his early years at RCA Victor. He recalled how Chet Atkins, the famously reserved Nashville producer who signed him in 1966, could never hide his admiration whenever the couple walked in and always remarked on what a striking, beautiful woman Rozene was. For a Black couple navigating 1960s and 1970s Nashville, that respect from one of country music’s quietest gentlemen stayed with Charley for more than half a century. Beaming like the 22-year-old baseball player who first met a young cosmetologist by a Memphis ballpark in 1956, he told the reporters that Rozene also had a sharper business mind than he did, managing their family and career so he could focus on singing. No one in that room knew he had just 31 days left to live before passing away from COVID-19 complications in Dallas on December 12, 2020. After winning Grammy Awards, entering the Country Music Hall of Fame, and receiving a lifetime achievement trophy, Charley used his last moments before the cameras to make sure the world knew how much he still admired his bride.