Waylon Jennings: Righteous Outlaw Until the End (2002)

courtesy Hot Schatz PR

Originally published in the March 19, 2002 issue of Country Weekly magazine. 

The cold is unbearable in Clear Lake, Iowa. 

Twenty-one-year-old Waylon Jennings, playing bass on tour for Buddy Holly, has just given up his prized seat on a chartered plane to J.P. “Big Bopper” Richardson. He will travel by bus instead. 

“I hope your damn bus freezes up again,” teases Buddy. 

“Well, I hope your old plane crashes,” responds Waylon with a chuckle. 

When the bus pulls into Moorhead, Minn., Waylon learns that his joke has come horribly true – Buddy’s plane has crashed, killing all aboard.

Fate spared Waylon Jennings’ life on Feb. 3, 1959. Waylon had been given a second chance, and he used it to change the world of music forever. And after he had done that, Waylon Jennings died peacefully as he slept on Feb. 13, 2002, at age 64

“Waylon kicked ass right to the end, and ruled the roost right up to the last minute,” says his wife of 32 years, Jessi Colter. “Waylon always did things his way, and even won the final battle, because he got to die his way: at home and in his sleep.”

The man who had spearheaded the 1970s “Outlaw” movement, unleashed classics like “Luckenbach, Texas,” “Amanda” and “I’m A Ramblin’ Man,” and changed the way business was done in Nashville, died at his house in Chandler, Ariz. 

His road had begun some 700 miles east of Chandler: Waylon Arnold Jennings was born in Littlefield, Texas, on June 15, 1937. There he grew up poor, idolizing country stars like Ernest Tubb, Hank Williams and Carl Smith. He began making his own music at an early age – as he wrote in his autobiography, “It was a way out.”  

By his mid-teens he was working as a radio DJ in nearby Lubbock, where he met hometown boy Buddy Holly. Buddy took young Waylon under his wing, producing his first recordings. (Those early songs are collected in a new album, Phase One: The Early Years 1958-1964.) “Buddy was the first person to have faith in my music,” Waylon recalled later. 

After Buddy’s death, Waylon settled in Phoenix, where singer Bobby Bare heard him sing at a club. On Bobby’s recommendation, Chet Atkins – then a producer for RCA Records – gave the brash youngster a shot.  

Wild-eyed Waylon bumped heads immediately with laid-back Chet over control of his music – the first of many dustups with the Nashville establishment. Nonetheless, he began scoring hits: his first Top 10, “(That’s What You Get) For Lovin’ Me,” came in 1966, and he reached No. 2 with “Only Daddy That’ll Walk The Line” two years later. By then, Waylon had moved to Nashville, at first rooming with fellow hellion Johnny Cash – which only increased the amount of trouble he could get himself into. 

In 1969, a calming influence entered Waylon’s life when he married fellow singer Jessi. The marriage, his fourth, would last for the rest of Waylon’s life. “I never got tired of her,” he once said, “and she never got tired of me, I guess. She’s the most even-tempered person I ever met.”

The couple would have one son, Waylon Albright, nicknamed “Shooter,” in 1979. Waylon already had sons Buddy and Terry and daughters Julie Rae and Deana from previous marriages, and he adopted two daughters: Tomi Lynne, and Jessi’s daughter Jennifer. 

In the early 1970s, Waylon began securing his position as a country outsider – a baritone-voiced, black-hat-wearing rabble-rouser who succeeded despite breaking all the rules. With the aptly-titled 1973 album Lonesome, On’ry And Mean, he began producing his own records and letting his regular band play on them – both Nashville no-no’s. “It was a big battle for me to get control of my career,” he said later. 

Just as Waylon was straining at the Nashville leash, some like-minded compatriots – such as Willie Nelson, Tompall Glaser and his own wife, Jessi – were doing the same. In 1976, RCA released an album of cuts by those four rebellious artists, calling it Wanted: The Outlaws. It was an instant smash, becoming the first country album to sell a million copies and bringing the underground “outlaw” movement to the masses. 

But just as Waylon’s career was hitting its heights, a punishing $1,500-a-day cocaine habit was wreaking havoc in his personal life. In 1977, he was charged with conspiracy and possession of cocaine with intent to distribute, although the charges were later dismissed. Waylon finally kicked the habit cold turkey in 1984.

By then, the “outlaw” was revered in the business whose rules he had railed against so furiously. His 1979 Greatest Hits album had sold four million copies, he had made two smash duet albums with Willie, and he had spread his fame to a younger generation via his voice-over role as “The Balladeer” on The Dukes Of Hazzard. In 1985, Waylon teamed with fellow renegades Willie, Johnny Cash and Kris Kristofferson to form the supergroup The Highwaymen.

But as Waylon’s mythic stature grew, time started taking its toll on his body. He had a triple-bypass in 1988, and surgery for carpal tunnel syndrome six years later. Illness all but forced him to stop touring by 1998.

By then, Waylon had made peace with his place in the music world. “I was king of the mountain one time,” he said. “But if somebody said to me, ‘You can be the number-one singer in the country again,’ I would say no. I like it right where it is.”

Last October, Waylon was given the ultimate symbol of acceptance by the Nashville establishment: induction into the Country Music Hall of Fame. True to form, he did not show up to accept the honor. 

Perhaps it wasn’t just stubbornness, but poor health that kept him from appearing. Waylon’s left foot was amputated two months later and replaced with a prosthetic one. In January, he left the hospital and returned to the Arizona home to which he and Jessi had moved just over a year before. 

And on Feb. 13, the endlessly restless spirit of the man they called “Waymore” moved on from this world. 

He was once asked how he’d like to be remembered. “I was a good ol’ boy,” he said. “As good as the best, and as bad as the worst. That’s about it in a nutshell.”

Waylon’s Hits & History

Many of Waylon’s victories – for artists’ rights and musical freedom – were won behind the scenes. Here are a few of his more public achievements:

  • He racked up 16 No. 1 hits and recorded more than 60 albums in his lifetime. 
  • Two Grammys, both for Best Country Performance By a Duo or Group – one for his version of “MacArthur Park” with The Kimberlys (1969), and the other for “Mamas, Don’t Let Your Babies Grow Up To Be Cowboys,” one of many duets with friend Willie Nelson (1978) 
  • Four CMA awards: Male Vocalist of the Year (1975), Vocal Duo of the Year (with Willie, 1976), Single of the Year (“Good Hearted Woman,” 1976) and Album of the Year (Wanted: The Outlaws, 1976) 
  • One ACM Award, for Single of the Year (“Highwayman,” with Willie, Johnny Cash and Kris Kristofferson, 1985)
  • Induction into the Country Music Hall of Fame (2001)

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