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Dierks Bentley: Road Dogs

Web-exclusive outtakes from our Sept. 21 cover story

The Sept. 21 issue of Country Weekly features our latest cover story on Dierks Bentley, focusing on his life on the road with beloved dog Jake, as well as his music and his growing family at home. Presented exclusively here at is some more of our candid and wide-ranging discussion with Dierks.

What was the hardest part about getting a break in the music business?
Getting your foot in the door is tough. I worked all over town. I worked at CMA, TNN, the Hall of Fame, the Gospel Music Association. I temped all the way up and down Music Row through a temping organization called Randstad. Sometimes you feel like a loser. I remember working at this driving range cleaning golf balls, and the kid I was cleaning golf balls with was 14 and I was 26. It was like, ‘God, I’ve got a college education and I’m cleaning golf balls at a driving range. What the hell am I doing?’ That’s tough. Your parents questioning what you’re doing. Sometimes the only person that believes in you is yourself. It’s crazy to think back on it. The good old days are good because they’re old. A lot of great times, but there were a lot of moments of doubts, a lot of lonesome times.

Does any one gig stand out as the worst you ever endured?
There’s never been a bad show. Not one, from the crappiest little bar to a middle-of-the-day hot fair, to a night when I was really tired before I walked onstage. I’ve always found a way. Not just for the fans, but for the crew that has worked so hard for me, the band, and their families that are all riding this star together. If you’re fighting your way through a rough night, if your guitar’s out of tune or you break a string or something’s not working, just jump offstage and go into the crowd or pull someone up. Find a way to break that fourth wall between you and the crowd. Now the most painful gig would probably be Biloxi, Miss., with [Kenny] Chesney in 2004, when I jumped off a riser and tore my ACL [knee ligament] completely in half. I’ve still got the scar. But as far as just a bad gig, I can’t say we’ve had one.

You often surprise fans by heading into the parking lot before shows in your Jeep. What model is it?
It’s a ’77 CJ-7. The doors come off, the roof comes off—it’s made for tailgating. I’ll drive through festivals and people won’t know or care who I am. They’ll just be like, “Dude, great Jeep. What you got underneath there? Is that a six-popper? Has it got a V-8?” I’m like, “Uh, I don’t know. It’s got some sort of engine. It goes forward when I put it in first.” It’s an inline six-cylinder. When we go out into the parking lots it’s a bigger star than I am.

How long have you had it?
I got it three years ago. I remember I wanted to buy it, but I couldn’t find my checkbook that day. I was out with [wife] Cass getting some breakfast one day and I was all set to go buy it at 2 o’clock in the afternoon. I said, “Do you have your checkbook on you?” She said, “Yes.” I said, “Do you want to go look at a car? Let’s check this thing out.” She’s like, “All right.” We get there and she’s like, “You’re buying a Jeep for the road, aren’t you?” I’m like, “Well, not me, necessarily—I don’t really have a checkbook on me. But I thought maybe you would buy it.” So we always laugh about that: It’s the Jeep that I bought for her that she paid for that I actually drive.

How do you transport it on tour?
In a trailer that cost twice as much as the Jeep! The Jeep was four grand and the trailer was at least twice as much. I used to carry motorcycles, and I loved that, but riding a motorcycle is such a solo deal. With the Jeep you can bring other guys in the band along, or crew guys, go work out or something. It’s a lifesaver out here. A lot of times the schedule says you’re playing Chicago, but really you’re playing 20 minutes outside Chicago. To be able to get around is great.

You go back and forth between playing large and mid-size venues. Does that help keep things interesting?
One thing that makes the road great is having that variation. Just doing one thing all the time gets old. Next year I want to get out there with [Cross Canadian] Ragweed and do a small bar tour. You can’t always be on a stage that’s nine feet tall and seven feet away from the audience. I like jumping into that mosh pit of people, I like getting my hands dirty. Playing a small stage, there’s no defenses. An element of fear comes into play, which is nice. That heightens your senses. There’s nowhere to hide. People can yell at you, pour tequila on your boots. It hones your edges, keeps you sharp. I think playing small rooms tests us. It’s just like the greatest movie ever made, Young Guns: Billy the Kid says, “You’ve got to test yourselves every day, boys. You stop testing yourself, that’s when you become slow. And that’s when they kill you.”

A Nashville newspaper recently published the address of your new house. Did that bother you?
I think it’s kind of a dick move to do that, but what can you do? That’s the world we live in. I wish they wouldn’t, but there’s nothing I can do about it. It’s just the way it is. We have an alarm system. I have dogs, we have several guns. My wife doesn’t look like she’d be a gun person, but I’ve made sure she’s comfortable using one. The guy that did it had to go out of his way to do it, just looking for a reason to be a jerk. If he sleeps well at night, then good for him. If I don’t sleep well one night because of him, then he won’t be sleeping well. I’ll put it that way.

Have you ever had a problem with stalkers?
I haven’t. I think if you remove the pretense of trying to be a celebrity, people treat you pretty normal. I’m such a regular dude. I stay low-key and down to earth. I live in Nashville. I’m always out walking around. I don’t travel with an entourage. I’ve been living in town for 15 years. I know a lot of people in Nashville. It’s a great city. Even around CMA Music Fest, country fans tend to be pretty cool. I’ve got great fans.

Everyone knows about Jake, but how did you find your newest dog, George?
I was working on the [Feel That Fire] record, and Jake was in the studio with me. Jake started barking like crazy, I looked out the window and there this dog was. I let Jake out and immediately he went over and his tail started going back and forth, which is weird. He really liked him. He had a collar but no tag, so I put up signs all over town saying ‘Found Dog.’ Ended up falling in love with that dog.

What are your plans for the next few months? Will you have some time off in the winter?
I am really looking forward to November, December and January and February, and getting back into the creative zone. For a while there I was just using one gear, wide open, doing it all at the same time. But I do enjoy the process of getting away from the road and working on music. Take time to set up a tour, then you’re touring and not having to worry about music. I’m just getting a chance to do that now because we’re having some success. I guess that scales it back a little bit.

Do you have a long-term goal at this point?
I think the goal still just involves having a great collection of music that you can look back on and be proud of. I know that sounds cliché, but it’s about trying to write great songs and make great music. I want to keep going on tour, playing the biggest rooms we can play, going back out there and headlining our tour next year. Broadening out and trying new things. I do really want to make an album of bluegrass music and explore that area as well. It’s a huge love of mine. But basically I want to write great songs, make great records and, most importantly, put on the best live show that we know how.