Since Waylon Albright “Shooter” Jennings first made his presence felt on the music scene in 2005 with the release of Put the “O” Back in Country, he has maintained a streak of independence. Over the past decade he’s become a genre-busting musician, releasing albums that defy categorization — like the rock opera Black Ribbons and last year’s spoken word effort, The Magic. With constant touring, as well as a thespian turn in portraying his father in the Johnny Cash biopic Walk the Line, Jennings has managed to make himself known to music fans that otherwise might consider him just another struggling Americana artist. Jennings’ current tour has perhaps the largest amount of buzz since his debut album. And now, the singer takes the stage each night backed by Waymore’s Outlaws, former members of his father Waylon’s recording and touring band, The Waylors.

The City Paper managed to catch Jennings on the phone recently in-between gigs. “The tour is going great, man. Just, you know, having a good time,” the singer drawls into the phone. “I’m traveling around, playing with Waymore’s Outlaws, and just enjoying a pretty special experience. The crowds are great, we’re selling out rooms, and it’s nice.”

Concentrating on just entertaining a crowd of fans is a welcome change of pace for Jennings. A leading figure in the alt-country movement, Jennings started an indie record label in an attempt to harness the groundswell of support for a change in mainstream country music. His label, Black Country Rock, which also became the name of a genre, still produces new music, but the radio format was a venture apparently best left in the past.

“I was really trying to push that, but there became so much in-fighting that it became embarrassing,” the singer readily admits. “There was just so much bickering and anger that the only good thing to come out of it was that I met a lot of really good artists, a lot of really legitimate country artists. There are a lot of really great people in that scene, but there are also a lot of folks just copying those people in the attempt to get attention. There’s a lot of fighting involved in the genre right now.”

Jennings gives off the vibe of an artist who has waged a lot of battles in a short amount of a time. “There is fakeness in everything now,” Jennings says. “That whole attempt at gaining clout is so worn out. Country wanted outlaws, then bro-country stars, to now — I have no idea what’s going on.”

Figuring out what Nashville wants is something that Jennings has never had much of a desire to do. While his first three albums could all be comfortably placed under the country music umbrella, the raconteur could be found traveling the country as part of the Warped Tour and sharing stages with the likes of mall punk-rockers, Paramore.

This musical adventurousness has led to Jennings being embraced by a fandom that welcomes artists who takes chances. Meanwhile, detractors point toward his public disputes with fellow musicians, painting the singer as a wealthy young man prone to tantrums. Some have even questioned Jennings’ commitment to country music, using his Los Angeles home (and former wife, actress Drea de Matteo) and forays into the rock world (he joined L.A. rock band Stargunn in 2001) as evidence.

When asked if his appreciation of country music is a mere by-product of his upbringing, Jennings pauses a moment before answering.

“A lot of country music consists of really great songs,” the singer says, “so I think I would have found it sooner or later. There’s no way of really knowing or a real way to answer that. I think if I were to become a musician either way, good songwriting and composition would have drawn me to country, just because it’s so hard to ignore good music.”

And we all know that bro-country doesn’t necessarily rely on strong songwriting, and that’s why it’s slowly losing its grip at the top of the country charts. But Jennings has little hope that the next big gimmick to take its place will be much better.

“I don’t think there is much of a point in attempting to predict what the next phase of country music is,” the musician states emphatically. “I would think the seed that has been planted over the past 10, 12 years is going to continue to grow into the trees that the industry will lean on. Whatever is coming, or whatever form it will take, is always there in its own way. Look at Garth Brooks: when he was there at the top, as many people that fucking hated it would kill for him to be at the top again, just to get rid of what’s there now. And Garth can’t even sell records anymore!”

Jennings continues, “As far as the whole ‘bro-country’ thing goes, there was a band in the ’90s called Pop Will Eat Itself, and I always liked that because it’s true. It’s like all of the popular shit will just eat themselves until the next thing comes along. Everybody keeps saying they want a revivalist movement in country music, but that just means that three or four years after that movement comes through it’ll become uncool, just like Willie (Nelson) and Waylon became uncool.”

Jennings knows that he is no longer the young man who came onto the scene a decade ago, boldly proclaiming to have the cure for country music’s ills. Content for now to roll down the road with a few of his father’s friends, he reflects upon his beginnings for a moment.

“I’m not sure that it was a changing of my philosophy as much as I’ve just learned a lot over the time that I first started out. Just starting out by yourself, and building from the ground up, finding the right people that you feel understand what you’re trying to do,” he says. “I’ve learned a lot while not really changing my goals.”