Sure, he vowed never to become a country singer once - but never seriously.
"(I did) when I was a little kid," he confesses. "But that doesn't count. Because when you're little, you don't want to do what your parents did. And then you get older, and you realize, 'Boy, I'm pretty good at this!'"
These days, it's not so unusual to see Jennings' meld of rock with country, so his label doesn't really need to treat him like some kind of a unique case.
"I don't think they're doing anything special," he says. "I don't think they're trying to do anything different from what they do for anybody else. I think they're just trying to get my personality out there. My whole thing is that I'm a kid who loves rock and roll, and who loves his Seventies music. I love the Seventies country and rock and roll. I think it's all great, and I feel there are a lot of kids out there like me. And I feel like there is a whole generation of people that understand country in a whole different way and the old real artists, like the Waylons, and the Willies and the Merles and the Hank, Jr.s and the Johnny Cashes and the Jimmie Rodgers and the Hank Williams, Sr.s, you know?"
"There's a generation who appreciate that and appreciate those ' people telling their stories and the real deal. And I think what I want to do, and what the label wants to do, is just appeal to that audience, because I believe it exists. They're not being catered to, you know what I mean?"
However, his country music debut may have been delayed significantly, had he been asked to join one particular LA band that he once auditioned for.
"I sang with all those guys (from Guns 'N Roses)," he says. "It was basically Velvet Revolver. It was before they got Scott Weiland. They were auditioning singers and auditioned another guy and stuff. And then they asked me to do a show with them. I ended up doing a couple of shows with them. They asked me to do them, and it was awesome. It was crazy. I moved to LA because I loved that (Guns 'N Roses) band so much. And I was really excited about being in a rock band. But after I did that thing, I said, 'Well, I think I'm done with rock and roll right now.'"
Just like his dad, Shooter also has a wild side. He's certainly not been the perfect little church boy. But at the same time, he's smart enough to have avoided becoming yet another music business casualty."I feel like I've calmed down a lot," he explains. "We (speaking of his prior group Stargunn) were definitely the real rock band, so we were definitely wild and everything like that. But now that I've gotten a little older, I think I've settled down because Stargunn was a wild experience. Those guys were great, but drunk all the time, and that kind of stuff. Now I try to take it a little bit easier."
It's no secret that his dad battled substance abuses. But Waylon never took a heavy hand with Shooter when it came to teaching his son about this chemical dark side in the music business.
"He talked to me about drugs because he took drugs," Shooter says frankly. "He was on cocaine a lot in the Seventies, and whatnot. Basically, he just said it like this: 'I'm not going to tell you not to do it, and I'm not going to tell you that it's bad.' Because, he said, 'If I didn't have a family and all that, I'd probably still be doing it.' He said, 'When you have people that depend on you...when you live in a cave, you can do it. But when people depend on you, it affects them, and it's not fair to them.' It was a very good way of putting it. It definitely put me in a place where I was very balanced about it. Because a lot of kids whose parents say, 'Don't do drugs. It's bad, it's bad, it's bad.' They want to do it really bad. So he put me in a position of like, hey, 'You're probably going to mess around with all that stuff. But you need to know you can't do it and control yourself'."
Jennings had the distinct advantage of hanging out with other kids that knew exactly what it was like to be the daughter or the son of a music legend.
"Johnny, Willie and Kris' kids, I got to know a lot," he explains. "When I was younger, they (his dad and his dad's artist friends) were doing the Highwaymen thing, and we were all out on the road together at the same time. We so we all kind, in a way, grew up around each other. And we still connect. I still connect with different ones from time to time. I was talking with Amy Nelson just the other day. They're great people, and we're the only people in the world that understand each other because we've all been through the same thing. The same kind of gypsy life, that normal people don't really understand."
And does it concern Shooter that he'll forever be compared to his father's great accomplishments?
"No. I mean, I'm proud of that stuff. I feel like what I do is my own because I've been working at it for so long. It doesn't bother me. If they compare me to him, that's great. If they say I'm not as good as him, I'll agree."
No doubt about it: Shooter is a one honest, straight shooter, just like his old man.