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WAYLON JENNINGS FIRST SANG ON THE RADIO AT 12. TWENTY YEARS LATER, HE WON HIS FIRST MAJOR AWARD — FOR A SONG THAT SOUNDED NOTHING LIKE THE OUTLAW HE WOULD BECOME. Waylon Jennings was still a boy in Littlefield, Texas, when he began singing country songs on his own radio program. He was 12 years old. By 14, he was working as a disc jockey. He left school, formed a band and began chasing music long before Nashville knew his name. The road did not open quickly. Buddy Holly produced Waylon’s first record and hired him as a bass player. Then Holly died in the 1959 plane crash that Waylon survived only because he had given away his seat. Waylon returned to radio, played clubs in Phoenix and spent years trying to rebuild a career that had barely begun. RCA finally signed him in 1965. The records started reaching the country chart, but the awards still did not come. Then Waylon recorded “MacArthur Park” with the Kimberlys. At the 1970 Grammy Awards, the performance won Best Country Performance by a Duo or Group with Vocal. It was Waylon’s first Grammy and his first major national award. He was 32. Twenty years had passed since the 12-year-old boy first sang into a radio microphone. The trophy arrived before the black hat, before outlaw country and before “Good Hearted Woman.” America had finally rewarded Waylon Jennings—years before Nashville fully understood who he was becoming.

Waylon Jennings: The Boy Behind the Voice Waylon Jennings was still a child in Littlefield, Texas, when music found him…

THEIR FIRST ALBUM ARRIVED ON MAY 6, 1985. EXACTLY 3,863 DAYS LATER, JOHNNY CASH, WAYLON JENNINGS, WILLIE NELSON AND KRIS KRISTOFFERSON PLAYED THEIR LAST RELIABLY DOCUMENTED CONCERT TOGETHER. They were not four young singers hoping Nashville would notice them. By 1985, Johnny Cash, Waylon Jennings, Willie Nelson and Kris Kristofferson had already survived broken marriages, addiction, rejection, changing tastes and long years on the road. Each man had built a career strong enough to stand alone. Then they decided to stand together. Their first album, Highwayman, arrived on May 6, 1985. Its title song gave each man a different life: Willie was the highwayman, Kris the sailor, Waylon the dam builder and Johnny the traveler who would one day cross the universe. The song reached No. 1, and the album became both a country chart-topper and a platinum record. Over the next decade, they recorded three albums and carried four separate catalogs onto the same stage. A Highwaymen concert could move from “Folsom Prison Blues” to “Me and Bobby McGee,” from “Luckenbach, Texas” to “Blue Eyes Crying in the Rain”—four lives sharing one evening. On December 3, 1995, they performed at Neal S. Blaisdell Arena in Honolulu. The surviving setlist includes “Highwayman,” followed by songs that each man had spent a lifetime making his own. There was no planned ending written into that first album. But 3,863 days after it arrived, the road had quietly reached its final stop for all four men together. The title said the road would go on forever. The four voices had been given ten years, six months and twenty-seven days.

The Night The Highwaymen Rode Together for the Last Time They were never just four famous names on one poster.…

JESSI COLTER STAYED THROUGH THE FAME, THE COCAINE AND THE RECOVERY. AFTER 32 YEARS OF MARRIAGE, SHE AND WAYLON WERE GIVEN ONLY 110 DAYS OF THEIR 33RD YEAR. Waylon Jennings and Jessi Colter married in Phoenix on October 26, 1969. Both had been married before. Jessi already had a daughter, Jennifer, whom Waylon helped raise as his own. Ten years later, they welcomed their son, Shooter. Then outlaw country exploded. Waylon fought Nashville for control of his music. Jessi found success with “I’m Not Lisa.” In 1976, they appeared together on *Wanted! The Outlaws*, the first country album ever certified platinum. But the life behind those records was far more difficult. Waylon’s cocaine addiction grew until he was reportedly spending $1,500 a day. It damaged his finances, weakened his career and pushed his marriage toward its breaking point. Jessi could not fight the addiction for him. She could only decide whether there was still a man beneath it worth waiting for. She stayed. In 1984, Waylon finally quit cocaine. The recovery did not erase the years of pain, but it gave their family back the husband and father addiction had been taking away. Jessi remained beside him as diabetes slowly damaged his health. Waylon eventually stopped touring, and his final years became quieter than the outlaw days that had made him famous. On October 26, 2001, they completed 32 years of marriage. Waylon died from complications of diabetes on February 13, 2002. He was 64. Only 110 days of their 33rd year had passed. The world remembers the outlaw who refused to let Nashville control him. Jessi lived with the harder victory—the man who finally stopped letting cocaine control him, and came home to the family that had nearly lost him.

Jessi Colter Stood Through the Fame, the Cocaine, and the Recovery Waylon Jennings and Jessi Colter built a life together…

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