Los Angeles, California (CNN) -- The saddest-looking pair of black boots outside of a Goodwill bin sit in the corner of Dierks Bentley's dressing room at "The Late, Late Show with Craig Ferguson." Are they cowboy boots or motorcycle boots? No one really knows, because the style is completely obliterated by four neatly-wound rows of black duct tape.
"It's hockey tape," Bentley corrects. "Once I put my jeans on, you can't see anything except the tape. I've put a lot of miles on these boots. I feel like they deserve to go everywhere I've been."
The 34-year-old singer-songwriter has an instinctive need -- almost a gravitational pull -- to stay connected to his past. "I like old things. Old things have memories attached to them. It just makes them have character -- old guitars, old trucks, old boots."
Bentley was raised in Arizona, and at age 19, his dad helped him load up his Chevy pickup and move to Nashville, Tennessee. "I still own that truck. It's a special truck."
He's similarly attached to his well-worn acoustic guitar and is particularly proud of a fragile, half-inch hole below the pick guard.
It's a baby version of the big hole Willie Nelson sports on his instrument, the result of massive amounts of strumming. Nearby are autographs from some other legends: George Jones, George Strait, Del McCoury.
There's also a small cheat sheet taped to the top of Bentley's guitar. "It's actually embarrassing. It's the song 'Eastbound and Down' from 'Smokey and the Bandit.' I can probably take it off now because I do know it. But why?"
The six-time Grammy nominee's fifth CD for Capitol Nashville is called "Up on the Ridge."
Instead of offering up a new collection of rock-tinged country tunes and sexy, slow-burning ballads, he's released a bluegrass album, perhaps not what some where expecting from an artist with potential to cross over into the mainstream. But it pays homage to music that inspired him when he first moved to Nashville. In Dierks Bentley's world, a tree can't branch out without securing its roots.
The singer recently spoke with CNN about his new project, working with musical icon Kris Kristofferson and the Arizona boycott.
CNN: It kind of took some people by surprise that you put a bluegrass album out at this point in your career.
Dierks Bentley: I think my longtime fans knew that I was going to do something like this, because every record I've had has had a bluegrass track on it at the end. I moved to Nashville when I was 19, and discovered this world of acoustic bluegrass music, and I just thought it was really authentic.
CNN: You've got some great collaborators on the new album.
Bentley: I brought Alison Krauss in, of course, who's one of the greatest singers of all time, and then Jamey Johnson and Miranda Lambert, my friends from the country world. But then Del McCoury and Sam Bush and Tim O'Brien from the bluegrass world. And Kris Kristofferson. He's undefinable. He crosses all genres.
CNN: What was it like to get into the studio with an icon like Kristofferson?
Bentley: I had my iPhone out, and I'm like taping us while we're singing together in the vocal booth.
It was really fun. Couldn't be a nicer guy. He's one of those guys you look up to and hope you have some sort of career that would be looked upon the same way his was, just as far as leaving something behind that's worth remembering.
CNN: One of the great songwriters, but he also had the courage to speak up politically with some ideas that perhaps didn't sit well with some of his fan base.
Bentley: Kris is one of those guys like Merle Haggard. They can say stuff, and it doesn't come across as political. It comes across as authentic. It just feels like someone cares a lot about the country we're living in.
CNN: You've taken pains to not put yourself out there politically, but you're an Arizona native. Do you have any thoughts about the immigration bill that was just put into place?
Bentley: Having worked in Arizona many summers, I spent a lot of time with folks from Mexico that work their butts off every day building houses and stuff. They're the hardest-working people, and people that Arizona really needs to keep the economy moving forward. So it's a double-edged sword.
I understand that there's resources that are being used up that were not going into the system to pay for the hospitals, but at the same time, it's a pretty harsh way to deal with the situation. So I'm hoping a real policy will come out that everyone can kind of be happy with, but I think it's a pretty hardcore, pretty extreme way to approach the situation.
CNN: There are artists who are signing on to boycott Arizona. Do you think it'll be effective?
Bentley: I read about Willie Nelson doing some stuff, and as far as anti-Arizona stuff, I don't know. I try to find a middle ground in everything I do. You watch TV, and there's a left, and a right and nothing in the middle.
But I've toured the country. I've been touring for the last seven years. I hang out with folks every day in my Meet 'n' Greet. I meet a hundred people before the show, or I'm at a bar afterward hanging out, talking to regular folks all the time.
I find there's much more of a sense of common ground than you perceive if you just watch the different news channels. There really is a center, and I think in Arizona, they need to find that center.