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THE CREW FILMING THE HIGHWAYMEN AT NASSAU COLISEUM IN 1990 HAD ONE RULE: JOHNNY CASH COULD ONLY BE SHOT FROM ONE SIDE OF HIS FACE. It was March 14, eleven days after Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson opened the first tour they ever ran as a group, out behind Highwayman 2. The cameras in Uniondale were not there by chance. Lou Robin, Cash’s longtime manager, said everyone knew this was the show to film: a big crowd, and four men who had finally been on the road together long enough to trust each other onstage. They gave the crew two hours and thirty-nine minutes. They raided each other’s solo catalogs, “Folsom Prison Blues,” “Always on My Mind,” “Me and Bobby McGee,” “Sunday Morning Coming Down,” and kept stepping back so the next man could take a verse. At the end of Kristofferson’s “The Pilgrim: Chapter 33,” he pointed at each of the other three and grinned. Jessi Colter, Waylon’s wife, said they were always on it, but that one was fantastic. And Johnny Cash sang every minute of it with one side of his face turned away from the lens. Robin gave the reason in the liner notes, decades later, when the complete film was finally released in 2016. It was not the lighting, and it was not vanity.

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The One-Sided Light on Johnny Cash at Nassau Coliseum On March 14, 1990, The Highwaymen walked onto the stage at…

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WAYLON JENNINGS RECORDED 12 SONGS WITH ONLY HIS GUITAR, HIS VOICE AND ROBBY TURNER’S BASS. TEN YEARS AFTER WAYLON DIED, THE MAN BESIDE HIM RETURNED TO FINISH THEM. During the final years of Waylon’s life, he spent hours in the studio with Robby Turner, his longtime musician and close friend. Waylon sang and played guitar. Robby played bass. Together, they recorded the foundation of 12 songs and discussed the instruments that would eventually be added. But Waylon’s health was failing. He died on February 13, 2002, before the album could be completed. The recordings remained untouched for years. Then Robby received Jessi Colter’s blessing and brought several of Waylon’s longtime musicians back into the studio. Their guide was simple: finish the songs as Waylon would have wanted them. The work was not easy. While adding steel guitar to one track, Robby looked down and saw one of his tears fall onto the instrument. In 2012, the finished album was released as Goin’ Down Rockin’: The Last Recordings. Waylon was gone. But the men who had once played until he smiled came together one last time and finished what their friend had started.

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Waylon Jennings, Robby Turner, and the Songs Left Waiting for the Right Ending Some records arrive like a celebration. Others…

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JANIS JOPLIN PLAYED THE GUITAR PART HERSELF ON THE ONLY NO. 1 SHE WOULD EVER HAVE, AND SHE NEVER LIVED TO HEAR IT ON THE RADIO. She cut “Me and Bobby McGee” during the Pearl sessions in 1970, in the weeks before October 4, when she was found dead in a Hollywood hotel room at 27. Kris Kristofferson, who wrote the song with Fred Foster, was off in Peru working on a film. Bob Neuwirth had taught it to her. Kristofferson didn’t know the recording existed. The day after she died, her producer Paul Rothchild asked him to come to the office and listen. He said he walked all over Los Angeles afterward, in tears. In March 1971 the record reached No. 1 on the Billboard Hot 100, one of the first posthumous chart-toppers in the history of that chart, and the song that made his name as a writer. Then came the part nobody prepares for. Every audience wanted to hear it, and he couldn’t get through it. So he sat down with his friend Donnie Fritts and they played Joplin’s version over and over, until he could listen to it without coming apart. He sang it for the rest of his career. He said he thought of her every single time.

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Janis Joplin, “Me and Bobby McGee,” and the Song She Never Heard on the Radio There are songs that become…

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CHET ATKINS WAS THE GUITARIST NASHVILLE TRIED TO COPY. THEN JERRY REED CAME ALONG, AND EVEN “MR. GUITAR” BEGAN LEARNING FROM HIM. When Jerry Reed arrived at RCA in the mid-1960s, Chet Atkins was already one of the most respected men in country music. He was a legendary guitarist, a successful producer and the man who had helped shape the Nashville Sound. But Chet heard something different in Jerry’s playing. Jerry did not pick the guitar like anyone else. His fingers attacked the strings with unusual rhythms, sudden pauses and complicated patterns that seemed almost impossible to repeat. Instead of asking Jerry to become more conventional, Chet encouraged him to sound like himself. Then something remarkable happened. The established master began incorporating some of Jerry’s musical ideas into his own playing. Chet recorded Jerry’s songs, shared the studio with him and treated the younger guitarist not as a student, but as an equal. In 1971, their album “Me and Jerry” won a Grammy for Best Country Instrumental Performance. Jerry had entered Nashville hoping to earn the respect of one of his heroes. He left behind something even greater. He had given “Mr. Guitar” a few new things to learn.

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Chet Atkins and Jerry Reed: When the Master Learned Something New By the mid-1960s, Chet Atkins was already a giant…

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WHEN THE STATLER BROTHERS RETIRED, THREE MEN WERE READY TO STOP. JIMMY FORTUNE WAS 47—AND HAD TO LEARN HOW TO BEGIN AGAIN WITHOUT THEM. On October 26, 2002, The Statler Brothers gave their final concert in Virginia. For 21 years, Jimmy had stood beside Don Reid, Harold Reid and Phil Balsley, adding his high tenor to one of country music’s most recognizable harmonies. When the last note ended, the other three stepped away from touring. Jimmy was not ready. But continuing meant starting over. There would be no Statler name above him, no three familiar voices surrounding his own and no guarantee that audiences would follow him. Jimmy considered writing songs and performing wherever he could. Then he chose to keep singing. In 2003, he released his first solo album. Its title said exactly where his life stood: “When One Door Closes”. The Statler Brothers had given Jimmy the greatest opportunity of his career. Their retirement took away the only musical home he had known for two decades. At 47, he did not try to replace it. He simply opened another door.

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When The Statler Brothers Retired, Jimmy Fortune Had to Begin Again On October 22, 2002, The Statler Brothers stepped away…

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DOCTORS THOUGHT KRIS KRISTOFFERSON WAS LOSING HIS MEMORY TO ALZHEIMER’S. THEN A LYME DISEASE TEST CAME BACK POSITIVE — AND AT 80, HE RETURNED TO THE ROAD. By his mid-70s, Kris was struggling to remember names, lyrics and what he had been doing only moments earlier. Doctors suspected Alzheimer’s disease or dementia, possibly connected to the blows he had taken while boxing and playing football and rugby. He began taking medication, but his condition kept getting worse. Then, in 2016, a doctor tested him for Lyme disease. The result was positive. Kris stopped medications for illnesses he apparently did not have and completed three weeks of Lyme disease treatment. His wife, Lisa, said many of his symptoms improved, though some short-term memory problems remained. That same year, he toured again, including performances with Willie Nelson and shows in Europe. He also released “The Cedar Creek Sessions”, which earned a Grammy nomination. The family had feared they were watching Kris disappear. Instead, at 80, one of the Highwaymen found his way back to the stage.

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Doctors Thought Kris Kristofferson Was Losing His Memory. Then a Lyme Disease Test Changed Everything. By the time Kris Kristofferson…

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HE WROTE IT ALONE. NO CO-WRITER. THREE WEEKS AT NO. 1. June 1978. Waylon Jennings put out a song with nobody’s name on it but his own. Ten months earlier, federal agents had walked into a Nashville studio while he was standing at the mic, headphones on, singing harmony for somebody else’s record. August 23, 1977. He was arrested that night. The case never held up. He didn’t dodge it afterward. He opened the song by owning the arrests — the ones that were his doing, and the ones that weren’t. He refused to say he was proud of any of it. But there was one thing he would not let anyone take from him. One sentence he wrote in his own defense, and it’s the reason people still hear that song as an apology instead of a brag. Then the third verse turns. He stops talking about himself and speaks directly to a woman — and it isn’t a love song. It’s a warning. Sixth No. 1 of his career. Thirteen weeks on the chart.

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Waylon Jennings and the Song That Sounded Like a Confession In June 1978, Waylon Jennings released a song that stood…

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IN 1995, A WRITER WALKED INTO WAYLON JENNINGS’ LIVING ROOM AND FOUND HIS WIFE SINGING SCRIPTURE. Lenny Kaye was there to help Waylon put his autobiography together. Jessi Colter went to the piano with a Bible near her and began setting the Psalms to melodies she was inventing as her hands found the chords. Kaye said he was transfixed. Jessi has said it wasn’t something she normally did. It fit her, though. Her mother was a Pentecostal preacher who performed her wedding to Waylon in Phoenix in October 1969, and Jessi had been the church pianist since she was eleven. She married a man with three marriages behind him, and she stayed through the cocaine years that nearly ended the marriage in the early 1980s, through the heart bypass in 1988, through the diabetes, through the amputation of his foot in December 2001. In her memoir she writes that Waylon came to faith that Thanksgiving. He died in his sleep on February 13, 2002. She and Kaye finally recorded those songs in New York in 2007 and 2008, just her voice and piano and his guitar. They came out in March 2017 as an album called The Psalms, twenty-two years after the first of those melodies was played in a house where Waylon Jennings was still alive.

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The Day Jessi Colter Turned a Living Room Into Scripture In 1995, Lenny Kaye walked into Waylon Jennings’ living room…

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IN OCTOBER 2016, RANDY TRAVIS ROSE OUT OF HIS WHEELCHAIR AT THE COUNTRY MUSIC HALL OF FAME AND SANG — THREE YEARS AFTER DOCTORS TOLD MARY TO LET HIM GO. The room at the Medallion Ceremony went silent because nobody in it expected a sound out of him. He had not sung in public since 2013 and still could not put a full sentence together, so Mary read his acceptance for him. Then she said, “Randy stared death in the face, but death blinked,” and handed him the microphone. Garth Brooks was crying before the first verse ended. She had watched every inch of it. In July 2013 a virus settled in his heart and put him in a Texas hospital with both lungs full of fluid. His heart failed, he went on life support, and a stroke took the voice. One to two percent was the number the doctors gave her. Months later a staph infection and other hospital-borne bacteria piled on, and his team told her he did not have the strength left for any of it. Before she gave them an answer, she went and stood at his bed. He could not speak, could not sit up, could not tell her anything. He squeezed her hand, and a tear ran down his face. She turned around and told the doctors that man wanted to fight, and they were going to fight with him.

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When Randy Travis Stood Up and Sang at the Country Music Hall of Fame In October 2016, the Country Music…

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HE BURIED HIS WIFE AND MOTHER WITHIN WEEKS OF EACH OTHER. A YEAR LATER, HIS ONLY SON DIED. THEN BILLY JOE SHAVER’S HEART GAVE OUT ONSTAGE — AND HE KEPT SINGING. In 1999, Shaver lost his mother and his wife, Brenda, to cancer within a month of each other. Then, on New Year’s Eve 2000, his 38-year-old son Eddy died from an accidental heroin overdose. Eddy was not only his son. He was the guitarist who had stood beside him onstage and helped write “Live Forever.” Billy Joe later admitted that after those losses, part of him wanted to die. On August 25, 2001, while performing at Gruene Hall, the oldest dance hall in Texas, he suffered a massive heart attack. But he continued the show long enough that much of the audience never realized what was happening. He thought Gruene Hall might be a fitting place for an old outlaw to die. “It didn’t work out,” he later joked. Doctors performed a quadruple bypass. Billy Joe survived, returned to the studio, released another album in 2002 and kept performing for nearly two more decades. He had already buried the three people closest to him. But when his own heart tried to stop, Billy Joe Shaver kept singing.

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When Billy Joe Shaver Kept Singing By the time Billy Joe Shaver reached the stage at Gruene Hall, he had…

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Fifteen years after John Denver and Annie Martell’s marriage ended, Annie revealed something unexpected after his death: her favorite John Denver love song was not “Annie’s Song.” John and Annie married in 1967, when they were both young. Years later, after a difficult period in their marriage, John went skiing in Aspen. While riding a chairlift, the words to “Annie’s Song” came to him. He returned home and wrote down one of the most famous love songs of the 1970s. Annie later said she still cried when she heard it. But their marriage did not survive. They separated in 1982 and eventually divorced. During that painful period, John wrote another song for Annie: “Perhaps Love.” John died in a plane crash on October 12, 1997. He was 53. The very next day, Annie was interviewed about him. She said her favorite song of his was “Perhaps Love.” Not the song John wrote when their love was strong. The one he wrote while they were losing each other.

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Kris Kristofferson bought a ticket to Nashville in November 1970. He never used all of it. He met Rita Coolidge at the gate in Los Angeles. They were on the same flight and talked the whole way, and when the plane stopped in Memphis, he got off with her. Before that night ended they had already picked a name for a child they hadn’t had yet. She called it love at first flight. They married in 1973. Their daughter Casey was born the next year. They won two Grammys singing together. Then it came apart. They divorced in 1980, and when Rita finally wrote about it, she softened nothing — the drinking, the betrayal, crying every single day. She said it was not a good way to live. She asked for nothing when she left. But around that same time, asked about Kris, she wasn’t bitter at all. She said the two of them still had a bond nobody else could follow. Asked whether they might ever sing together again, she smiled and said, “Never say never.” They never got the chance. Kris died on September 28, 2024, at his home in Maui. He was 88. By then they had been divorced forty-four years.

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In 1978, Willie Nelson gave Columbia the last kind of album anyone expected from the face of outlaw country: ten old pop standards, some of them written before he was born. Willie had wanted to make that record for years. The problem was finding someone who could arrange songs as sophisticated as “Stardust” and “Moonlight in Vermont” without burying the way he naturally sang. Then he met Booker T. Jones. The legendary soul musician happened to be living in the same Malibu apartment building. Willie asked him to arrange “Moonlight in Vermont.” When he heard what Booker T. had done with it, he knew he had found the man to produce the entire album. Columbia executives were far less certain. Willie later remembered that they looked “stunned” when they heard what he was making. The audience answered for them. Stardust reached No. 1 on the country album chart. “Georgia on My Mind” and “Blue Skies” both became No. 1 country singles, and the album remained on Billboard’s country album chart for a decade. Willie Nelson had built his reputation by refusing to sound like everyone else. Then Booker T. Jones helped him prove that even the oldest songs could sound completely like Willie.

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In 1968, Kris Kristofferson was driving from Nashville toward the Gulf of Mexico when the end of a real relationship began turning into a song. He called it “For the Good Times.” Kris wasn’t writing about anger or trying to win someone back. The relationship was over, and the song simply imagined two people spending one last tender moment together before saying goodbye. Two years later, Ray Price recorded it. Price had been one of country music’s biggest stars, but he had gone 11 years without a No. 1 country single. On March 16, 1970, he walked into Columbia Studio A in Nashville and recorded Kristofferson’s song with a full orchestra behind him. That version changed things for both men. “For the Good Times” reached No. 1 on the country chart and crossed all the way to No. 11 on the pop chart. For Price, it was his first country chart-topper in 11 years. For Kristofferson, it became his first No. 1 as a songwriter. Kris had written the song because something in his own life was ending. Ray Price sang it, and suddenly two careers were beginning a new chapter.