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REVIVAL: Son of a Highwayman Shooter Jennings revives the legendary outlaw supergroup

by Joel Elliott

Occurrences later deemed legendary sometimes arrive by happenstance. As Waylon Jennings told it, The Highwaymen first came to be in the winter of ’84. He and Willie Nelson and Kris Kristofferson were all in Switzerland doing Johnny Cash’s television Christmas special.

“We got along so ‘handsomely’ as John put it,” Waylon later wrote. “We started trading songs in the hotel room after we worked on the special, and someone said, like they always do, we ought to cut an album.”

Sometime after, Willie and Johnny were in the studio working on a duet for Johnny’s latest album when Waylon dropped by for a visit, and later, Kris wandered in. They remembered the Jimmy Webb song, “Highwayman” that they had liked so much in Switzerland and since they were all there, in a studio together, they decided to record it. It would become their namesake. Their anthem. The first song on their first album: The Highwaymen. They didn’t write it, but in that moment, it became their own.

The original Highwaymen, clockwise from upper left: Johnny Cash, Waylon Jennings, Kris Kristofferson, and Willie Nelson

Waylon’s son, Waylon Albright “Shooter” Jennings, was born at the height of his father’s legendary, unhinged and drug-fueled guerilla rearrangement of a rapidly stagnating Nashville music scene dominated primarily by executives. Backed by his pit bull of a lawyer, Waylon and his friends did things their way and took no prisoners. They wrestled creative control away from the “suits” and put freedom in their own hands and in the hands of fellow artists. In reward for embarking upon such a grand bender, and along the way kicking the establishment firmly in the figurative groin, they became affectionately known as the “outlaws” of country.

Having spent the first several years of his life in a crib on Waylon’s tour bus, Shooter is no stranger to those original country outlaws and that extended family of misfit and rebel troubadours that always have been and forever will be queens and kings of the road. At five years old, he was out on tour with the original Highwaymen. So, it fits that he should be the one to bring them home. Introduce them to a younger audience that may not yet understand. Reintroduce them to those that remember. Was a time when those voices were found only on carefully tuned dials between walls of static sound or grinding through jukes and tin cans from dusty 45’s.

“Those guys really loved each other. They were all close friends, and that’s where the magic was,” observed Shooter, speaking from a place few have stood, before pivoting to the future, “I want this to be my version of this. I want to bring in family, and I want to bring in friends.”

The Revival began at last year's BeachLife Ranch, when Shooter brought in a widely varied group of musical luminaries to bring his father’s songs back to a live stage. Backed by Mike and The Moonpies, the first revival featured Devon Allman, John Doe, Orville Peck, White Buffalo, Chris Shiflett, James and the Shame, Gethen Jenkins, John Brennan, Willie’s son Lukas Nelson, and of course, Shooter’s mother, Jessi Colter, Waylon’s great love. The spunky little lady he allowed to tame and save him.

This year’s Revival promises a roster picked from the festival’s eclectic lineup, including reigning outlaw Cody Jinks. And, as one would expect from the son of an outlaw, Shooter’s got some surprises up his sleeve.

“Let’s do this every year,” he said, “and let’s make it bigger and better every time.”

In his own music, Shooter has done everything from industrial rock to R&B and back again. He’s established a distinct voice for himself. But when he’s doing country, there’s an unmistakable family resemblance that finds its way through the work. And he embraces it. The elder Waylon has bestowed in his boy the undeniable Jennings thunder and vocal depth first honed before the sawdust, the fists and boot heels, and the flying beer bottles of the dives and the honky tonks.

There are things in life, the great cycle that it is, that we are unable to escape. Where we come from, what we are, and where we might go in the end. Certainly, these four highwaymen, legends though they remain, could not have known what prophetic significance their cut of the song might someday hold.

“I was a highwayman,”meanders Willie, as he does, before imparting a legendary and entirely illicit tale of gallant and adventurous exploits. “The bastards hung me in the spring of ’25. But I am still alive”

“I was a sailor” Kris laments, in that aching voice of his. Having round’ the Horn on his way to Mexico, he climbed aloft in a blow, “and when the yards broke off, they said that I got killed. But I am living still.”

“I was a dam builder,” growls Waylon, somehow gently, from beyond. Bare hands having helped construct a monolith across the wild Colorado, “where steel and water did collide,” like country, he gave it everything he could. And then a little more. In the end, having firmly established himself as a permanent part of its very foundation. That great history, full of sound. “I slipped and fell into the wet concrete below. I am still around….I’ll always be around.”

And then with a boom: “I’ll fly a starship.” It’s Johnny doing just what Johnny does. Effortlessly making it sound big. Bigger’n that even. Chock full of middle finger. There he is out there somewhere up ahead, blasting fearlessly through the void, having gone to take a look at exactly just what’s beyond, “across the universe divide/and when I reach the other side/I’ll find a place to rest my spirit if I can/I may become a highwayman again/or I may become a single drop of rain /but I’ll be back again and again and again and again…”

The Highwaymen are back, just as they promised us they would be. This time around, a much younger Waylon will be plugging into the familiar hum and buzz of the gig. It’s been nearly 40 years since Switzerland. This time around, it may not be Willie or Kris, or John but when The Highwaymen take the stage, a connection will be made to a time when four close friends sat laughing and singing together just for the sake of laughter and song.

Shooter Jennings Revival takes place September 23 at BeachLife Ranch.


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