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Waylon Jennings: Outlaw

by Legacy Staff

Sometimes country singer Waylon Jennings was just a little bit more than the law would allow.

Waylon Jennings, one of the prime movers behind the Outlaw Country sound of the 1970s, was an outlaw in more ways than one. Not only did he insist on recording country music outside the bounds of the mainstream Nashville sound; he also cultivated a bad-boy image that ranged from temperamental behavior to an arrest for cocaine possession.

Born in Littlefield, Texas on June 15, 1937, Jennings learned to play guitar at age eight and formed his first band at age ten. He was meant for the music world, but he almost didn’t make it past age 21.


As a young DJ, Waylon Jennings met Buddy Holly, and the two musicians became friends. They began playing together, and Holly invited Jennings to play bass on his 1959 Midwestern “Winter Dance Party” tour. On February 3, Jennings was prepared to get on a plane with Holly, Richie Valens and others. Music fans probably know the fate of that plane — it went down shortly after takeoff, killing all the passengers. Jennings wasn’t one of those passengers only because he agreed to give up his seat to J.P. “The Big Bopper” Richardson, who was fighting a case of the flu.

Jennings’ career languished in the years after the crash (perhaps due to his severe survivor’s guilt). Then in the mid 1960s, Jennings began working as a session musician and recording his own albums, and he headed to Nashville to pursue country music fame in 1965. What he found when he got there were limitations.

In the decade before Jennings arrived in Nashville, country music had moved out of the hills and honky-tonks and into the mainstream, thanks to the Nashville Sound. With instrumentation inspired by pop music, heavy-handed production, and a smooth, citified sound, the country music hitting the charts in the 1950s and ’60s was very different from its roots, and it was the exact opposite of what Jennings wanted to play.

The Nashville establishment liked to use their own studio musicians — Jennings preferred his band, the Waylors. The Nashville Sound relied on lots of syrupy strings and crooning vocals — Jennings liked a rougher sound with more traditional country-music instrumentation. And the big label heads liked a certain sameness to the music they put out, playing to the masses — Jennings wanted artistic freedom to create the music that he liked.

Jennings began to fight the architects of the Nashville Sound, egged on by his new friend Willie Nelson. Nelson was based in Texas, successfully blazing a trail as an early outlaw, recording country music outside the establishment. Jennings took his inspiration from Nelson and, in 1972, pushed back hard against his record label, RCA. He ended up winning the battle and getting what he wanted: lots of money, lots of artistic freedom, and a shot at being one of country music’s first rock stars. He ran with his good fortune and started releasing records that were a blend of stripped-down rock ‘n’ roll and a throwback honky-tonk sound. His first few albums released under his artistic control did well, and then came 1976 — the year he released both Wanted: The Outlaws!, a compilation with Willie Nelson and others, and Are You Ready For the Country. Fans tired of the slick countrypolitan sound went wild for this edgy music played by guys who looked like long-haired rockers. Waylon Jennings became a superstar.

Suddenly, the outlaw sound was hot, and classic Nashville sounded stuffy and dated. Waylon Jennings and Willie Nelson collaborated on several songs that hit the country charts and even crossed over to the mainstream, including the smash “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.” Their albums went gold, platinum, even multi-platinum.

As his career as one of country music’s premier outlaws skyrocketed, Jennings became an outlaw in more ways than one. In 1977 he was arrested for cocaine possession (though the charges were eventually dropped due to police mishandling the case) and by 1980, he was an addict.

Neither the arrest nor the addiction hurt his career. Jennings landed a role on TV’s The Dukes of Hazzard playing The Balladeer, a narrator who always seemed to have the inside track on what was going to happen to the Dukes — particularly as their General Lee hung in the air in a freeze-frame cliffhanger. Not only did The Balladeer provide wisdom and humor — he sang the show’s theme song.

In 1984, toward the end of the show’s run, Jennings quit cocaine for good. About the same time, outlaw country began falling out of fashion. But being drug free and no longer the face of the outlaw movement didn’t make Jennings exactly squeaky clean. He kept up his bad boy image for the rest of his life — from storming out of a “We Are the World” recording session in 1985 due to a lyrics dispute, to refusing to show up for his induction into the Country Music Hall of Fame in 2001.

On February 13, 2002, just a few months after that final public act of defiance, Waylon Jennings died from complications of diabetes. But while he lived, his outlaw image helped change the face of country music. And it inspired future country artists to play outside the mainstream — from the ’80s roots rock of Steve Earle and John Mellencamp to the ’90s alt-country of BR5-49 and Uncle Tupelo, on through today’s neo-traditionalists like Old Crow Medicine Show and The Low Anthem. True, there’s still slick, over-produced country at the heart of Nashville’s mainstream… but as long as there’s a country music establishment, there’ll be outlaws of country like Waylon Jennings.

Originally published February 2011

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