Shooter Jennings went to Madison Square Garden a few weeks ago, saw Kanye West crash-land a spaceship and talk to computers on stage, and thought of one person: Dad. Joined by girlfriend/actress Drea de Matteo, Jennings had taken time out from his tour to catch West's otherworldly performance with Rihanna, Lupe Fiasco and Pharrell Williams' outfit N.E.R.D. He left the Garden blown away by not only West's showmanship, but the musical transcendence that conjured images of his father, Waylon.
"That's what I'm talkin' about, that's big. Back in the day, Willie [Nelson] and my dad did that," Jennings says. "They sold out the Hollywood Bowl one time in, like, '79."
Jennings has similar aspirations, but a much bigger dilemma. At 29, he wants to have his latest album, The Wolf, viewed in the same vein as works by indie acts such as Drive-By Truckers and Old Crow Medicine Show. He wants to tour with the Hold Steady and the Raconteurs, and to play festivals including Bonnaroo and Coachella. However, being born with the name Waylon Albright Jennings; playing with Charlie Daniels, Hank Williams Jr. and George Jones; and releasing a debut album titled Put the O Back in Country all tends to fuel certain expectations.
Jennings hasn't shied away from his country roots. He joined family friend and "Rainy Night in Georgia" writer Tony Joe White on mom Jessi Colter's 2006 comeback album Out of the Ashes, and portrayed his dad in the Johnny Cash biography Walk the Line.
Yet fond memories of working with Alice in Chains and seeing Nine Inch Nails on their Downward Spiral tour with Marilyn Manson echo his father's cosmopolitan approach to his craft.
"He grew up as Buddy Holly's protg, so he cared about music being this raw energy," Jennings says. "I think that's why he and Willie and those dudes could sell out the Hollywood Bowl because people in L.A. weren't into the Nashville sound, but liked them because they were great songwriters with a harder edge and spoke to other rock musicians."
Child of the road
If Jennings sees his father's experiences as the foundation for his own career, it's because he's been along for the ride since birth. From the crib installed in the back of Waylon and Jessi's tour bus, he shadowed his parents through most of his childhood. Summer vacations consisted of joining his parents on cross-country tours and jaunts overseas and eventually learning to play with his father's band.
"It wasn't until I was 16 that I started saying, "I don't wanna go, I've got friends,'" Jennings recalls. "I feel like they did a pretty good job and that I had a good model to look to."
It's a period Jennings has been revisiting more often since the birth of his and de Matteo's daughter, Alabama Gypsyrose, in November. Jennings, who started his solo career in 2005, has looked to Jessi for advice on how to raise a child through 250 tour dates a year.
"I've just been asking her normal questions, like, "How old was I when we went out the first time?' and "What was your crib like on the bus for me?'" Jennings says. "We kind of figured it out on our own, though."
Building on Waylon and Jessi's efforts, Jennings had his tour bus retrofitted with a "glorified sandbox" of a crib and stole a shopping cart from Babies 'R' Us to haul Alabama's belongings from the bus to various hotels. Such ingenuity has paid off thus far.
"She was out on the road for over a month and she handled it like a champ," Jennings says. "She didn't even cry she cried a total of an hour the entire month."
Branded an outlaw
That'll be the first trip of many for the youngest Jennings; Shooter's beginning his Volunteer Jam tour with Daniels and .38 Special after a run on the Axis of Justice tour with Rage Against the Machine's Tom Morello. He's also playing in Kansas with Merle Haggard.
But after Morello helped introduce Jennings to Hold Steady lead guitarist Tad Kubler, he's looking for a sound and status that's more Jack White than Clint Black.
"I don't believe my reach as an artist is restricted to the Dierks Bentley audience," Jennings says. "I hoped that there would be a place for an indie rock version of country music, but a lot of bands like the Drive-By Truckers have learned the same thing: Nobody wants to be Americana, nobody wants to be alt-country, they just want to play their music and get it out there. But there's no outlet for it."
The support Jennings has received within the country community has been tempered only by what he perceives as Nashville's indifference. He bemoans his lack of radio play and, despite a recent appearance on CMT's Unplugged at Studio 330, dismisses the country channel's awards broadcasts as "just the same crap every year," with few exceptions.
He talks bluntly about wanting "rock 'n roll money" and the freedom to leave the road every so often, but faces an environment in which artists considered country have to pack Central Park (Garth Brooks), threaten America's enemies with freelance proctology (Toby Keith), or be completely ostracized for telling Keith where to stick his boot (Dixie Chicks) to cross over.
The key to Jennings' indie rock dream comes in the independent spirit passed down not only from his parents, but from the artists he admires. Jennings has shrugged off country radio with his own show on Sirius' Outlaw Country channel, taken gigs with like-minded bands including Earl Greyhound, and released a pseudo-spoken track in "This Ol' Wheel."
"I'm not in the box that a lot of people put me in," Jennings says. "They've already tried to not let me do everything I've already done. Even if it's not realized until I'm long gone, I totally want to fuck it up as much as possible for everybody else."