The Songs of Waylon Jennings: Shooter Jennings and friends celebrate the late great Hoss

by Mark McDermott


Nobody brought the thunder like Waylon Jennings.

His thunder took many forms. Jennings rattled the suits in Nashville when he refused to play by the established music industry rules, growing long hair and a beard and seizing total artistic control of his work at a time when that was unheard of and in so doing launching the outlaw movement that reshaped country music.

Jennings was also a legendary hellraiser. There’s a story about a young Waylon holding court at a honky tonk one night and irritating an older man with his brashness, which led to a standoff.

“Who the hell do you think you are are?” the man said to Waylon. “You’re just a kid. You don’t know nothin’.”

“Sir,” Waylon cooly replied. “I may be younger than you, but I’ve been awake a long, long time.”

This was true figuratively and literally. Jennings lived several lives within his lifespan, which ended at 64 in 2002. In Waylon: Tales of an Outlaw Dad, his oldest son Terry Jennings, who toured with Waylon 13 years, recalled weeks they barely slept. Waylon sang about this, too, later in life, in a song called “I Don’t Do It Anymore,” “Stayin' awake, for a week at a time/Doing them doobies, and drinking that wine…’” But of course he also had a $1,500 a day cocaine habit. “I did more drugs than anybody you ever met,” he once told a reporter.

Waylon was thunderously prolific in all he did. His son recalled routinely booking four hotel rooms for his dad – one for his Waylon and his wife, and three for other women, each on a different floor.

“I thought it was my duty to take every woman that I could ever find that looked good and seemed like it was goin’ be alright….to take ‘em to bed,” Waylon later told Country Music Television. “And I did.”

“Here he’d come running up the fire escape, he wasn’t even using the elevator, taking care of all them girlfriends,” said Richie Albright, Waylon’s longtime drummer. “I said ‘Hoss, you goin’ to kill yourself.’”




Waylon was also a legendary a guitar player. He developed a signature Telecaster sound that combined Buck Owens’ Bakersfield Sound with rock ‘n roll, injecting a sharp-edged rawness into country music the likes of which the genre had never known. He was so naturally musically gifted that Buddy Holly, a fellow Texan, from Lubbock – not far from Littlefield, the little farm town Waylon came from – befriended him when he was still a teenager. Holly, at the peak of his stardom, showed up in town one day, and literally tossed Jennings a bass guitar. “You’re going on the road with me,” he told Waylon. “You have two weeks to learn this thing.”

That was the tour that ended tragically in a plane crash that claimed the lives of Holly, Richie Valens, and the Big Bopper. Jennings gave up his seat on the plane for the Big Bopper, and Holly good-naturedly gave him a hard time about riding the tour bus across the plains in the cold of Midwestern winter. “I hope that ol’ plane crashes,” were Jennings’ last words to Holly, a fact that would haunt him for decades to come.

The biggest thunder Waylon Jennings brought, however, was in his voice, and in the songs he sang. Maybe only Johnny Cash, his former Nashville roommate, had a voice that rivaled Jennings’ for its depth, largeness, and raw masculine power. But even the Man in Black followed behind Hoss in some significant ways. In fact, Waylon’s nickname is telling – hoss is a southern turn of phrase which means a big, strong man, who is dependable and can carry others like a horse. Waylon was the outlaw who led the charge – aided and abetted by a ruthless lawyer and manager named Neil “Maddog” Reshen – something that would not have been possible if he didn’t have that voice and that genuine badassedness to back it up.

“You start messing with my music, I get mean,” Waylon said at the time.

Waylon made Nashville play by his rules. He made the suits back down, seizing artistic control not only for himself but for all those who followed, from Cash to Nelson to current country stars.

“He really did stir it up and kick down a lot of doors,” Dierks Bentley told American Songwriter. “For the rest of us, a lot of things are taken for granted, like having a say on who plays on our records and writing our songs and how they sound. A lot of that is an ode to Waylon and his lawyer at the time, who really changed the way things were done in Nashville. I think he has a real mystique and coolness about him that you can’t manufacture.”

Once those doors were kicked down, the songs of Waylon Jennings cut loose across the land like a stampede. He released two records in 1973, his first recordings free of the Nashville assembly-line system of making records (often with string sections), Lonesome, On’ry, and Mean and the seminal Honky Tonk Heroes. He didn’t write most of these songs. Billy Joe Shaver wrote nine of the songs on Honky Tonk Heroes, which is now considered one of the greatest country albums of all time, along with Willie Nelson's Red Headed Stranger (Shaver reportedly barged into the recording studio and threatened to kick Waylon's ass if he wouldn't at least listen to his songs -- a credible threat, given Shaver would later shoot a man "between the mother and the f****r" in a honky tonk parking lot).

But every song he ever sang became a Waylon Jennings song. Over the next 10 years, Waylon had 14 number one hits, and the first country album ever to go platinum, Wanted! The Outlaws. He became the first country singer to reach rock star status, with a body of work that included “This Time,” “Amanda,” “Because You Asked Me To,” “I’ve Always Been Crazy,” “Good Hearted Woman,” “Luchenbach, Texas,” and “Mama Don’t Let Your Babies Grow Up to Be Cowboys” (the latter three with his good friend and fellow outlaw Willie Nelson). Later in his career, he scored a number one hit for his Dukes of Hazard TV show theme and served as its wise narrator, and formed the supergroup The Highwaymen with Cash, Nelson, and Kris Kristofferson. Even his very last record, Going Down Rockin’, recorded when he could barely hold a guitar due to the ravages of diabetes and surely knew his time was coming, contains that unmistakeable combination of defiance and sideways humor that set him apart. Country music was forever changed by Waylon Jennings.

Shooter Jennings, his only son by the last of Jennings’ four marriages, to Jessi Colter, the love of his life, has carried on his father’s legacy – both by most decidedly doing things his own way, but also by keeping Waylon’s songs sung. He’ll lead an all-star cadre of performers through a set of his father’s songs at BeachLife Ranch, including Lukas Nelson (Willie’s son), John Doe (of X), Yelawolf, Devon Allman, The White Buffalo, and at least one heralded country star whose name is being kept secret as yet by festival organizers.

Shooter, talking about a tribute record to his dad’s music a few years back, acknowledged that the songs of Waylon are an impossibly steep mountain to climb.




“I’m very passionate about my dad’s music but I’m always pretty skeptical of other people doing it,” Shooter told American Songwriter. “It’s never going to be the same as him, but that’s why I think we got some really good music when these people do it their way.”

The songs must go on. Hoss lives on through them, and in the artists who make independent country music in that same raw and defiant spirit as he did. Fifty years ago, when Waylon first broke out of the Nashville cage, his manager Maddog booked him at Max’s Kansas City, the hippest rock club in New York City at the time, with an audience that included Andy Warhol and other hipsters. Waylon knew this crowd didn’t know country music. He was undaunted. He announced at the outset that he and the band were from Nashville, they’d be playing country music, and they hoped everyone would like it.

“But if you don’t like it, you better keep your mouth shut, ‘cause we will kick your ass,” Waylon told the audience.

“Who the hell are you?” someone yelled.

“Waylon goddamned Jennings,” he replied, before tearing into his guitar and raising his voice to hell and heaven and back, a West Texas storm erupting before the stunned city folk. Because Waylon was the thunder.

Shooter Jennings, John Doe, Yelawolf, Devon Allman, The White Buffalo, and special guests yet to be announced play BeachLife Ranch September 17.


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