Dierks Bentley Doesn't Give a Damn About His Legacy

Dierks Bentley is searching for a signal.

This isn’t some kind of metaphor. The multi-platinum singer-songwriter is calling in from a beach in Florida and his phone connection is sketchy. Fighting through annoying technical challenges, though, is a small price to pay for taking advantage of a two-day break in his tour schedule to sneak in extra time with his family.

Bentley, 49, takes more pride in prioritizing his wife and three kids than in his 20-plus years of country music stardom—to the point of piloting his own plane to take his band on the road, for greatest efficiency in getting everybody back home. “I don't think anyone has been able to do it the way I've done, as far as incorporating my family time into the touring thing,” he says. “It's easy to chase the numbers when you're single or not a great dad, but it's a lot harder to do when you actually care a lot.”

But Bentley’s new album, Broken Branches (out now), mostly hearkens back to a different chapter in his journey. On his eleventh LP, he examines what drives young people to do something as crazy as move to Nashville and stake it all on the dream of being a musician.

Since he made that move himself from Arizona to Music City USA in the mid-‘90s, Bentley has gone on to a career of remarkable consistency, with eight Number One albums and 22 Number One singles on the country charts, while creating a distinctive and daring sound incorporating traditional bluegrass and U2-style anthemic rock. Though he’s never had a big crossover hit or celebrity spotlight moment, Bentley was recently recognized as one of the 20 biggest country artists of the 21^st Century by Billboard magazine.

The themes of the new album also led Bentley to establish the Broken Branches Fund, to provide mental health resources to the music community in partnership with Music Health Alliance. “We’ve always made sure that my guys and girls have health care on the road,” he says, “so we’re trying to bring awareness and hopefully some actual, real support.”

Before he runs off to rejoin his kids surfside, Dierks Bentley goes long on country music hopefuls, the emotional toll of a life in music, and how he measures his own success: “I found a long time ago, the work-life balance stuff—it's just one thing,” he says. “It's just life, and you’re either winning at that or you're not.” This conversation has been edited for clarity and length.

Esquire: Did you go into this album with any particular target?

Dierks Bentley: I really let the songs lead the way on this one. When I found the song “Broken Branches,” I'd already been working on the record for a year or so, but it really gave me a kind of core to dig in around—this idea that everyone in Nashville is some sort of broken branch off the family tree. I just love that idea, and so I really kind of built everything around that particular song.

ESQ: How did that shape where you went from there?

DB: I was thinking about myself moving to Nashville when I was 19 and exploring Music City and the highs and lows, the ups and downs, the heartbreak, the drinking—that was a big part of it. Faith, I went to so many different churches during that time, just searching, thinking all the time, trying to find some thread to hold on to and pull you through to the other side. All those themes are pretty pervasive in country music to begin with, but I came to this idea of leaving your family and going off and chasing a dream.

ESQ: You ended up writing less on this album than you usually do. Was that a choice, or was that just what shook out as you were going along?

DB: I've never had a lot of ego around writing my own songs, but the longer I do this, I just put more importance on the overall album and making something that really is structurally sound. I can write 70 songs—which I do every time—but alongside that, I can be pulling from thousands of songs, poring through them to find the ones that are a little bit different and say things in a way that I could never have said it. Whether I wrote them or where they come from, I care less and less every album. I’m just looking for the best song.

ESQ: You’ve never shied away from classic country wordplay in your lyrics. When you hit on a phrase like “Cold Beer Can” or the line “Jesus loves me but she don't,” do you have that feeling of, ‘Damn, that's been sitting there the whole time?’

DB: The difference between other kinds of songwriting and Nashville songwriting—the craft, the hours put into it, learning the wordplay and the editing—"Jesus Loves Me” is the song I’d play for anybody like, this is what good Nashville songwriting sounds like. That song blows me away, and that's another good thing about having songs on the record that you didn't write, is that you can really brag on them. I'm not going to sit here and talk about my songs, but that song is so good. Even a great songwriter probably gets two or three A-pluses per year, and I was lucky enough to find one of them.

ESQ: What inspired this mental health initiative you’ve started?

DB: It all ties back into this idea of broken branches. It's a different lifestyle you're choosing when you want to be a country singer or work in the business in any capacity. Leaving your family and friends behind can be isolating at times. It can be just like any workspace; it can be challenging.

ESQ: These issues have gotten so visible in the pop world. Is the country community as open to that discussion?

Oh, it's definitely wide open. You look at younger country singers’ Instagrams and social media, they're bawling, crying on there. They're very open with what they're feeling, what they're going through, there’s no shame or stigma about it now. These kids have brought it to the forefront of our consciousness, so we're not leading anything, we're just following their lead.

My generation was a little different. When I was raised, if my mom was stressed out, she would just say “I don’t believe in stress”. There's been times I wish I'd had this kind of support when I was going through it. But mine has been just country records and a beverage along with it; the music has been my therapy since day one. But I can't even imagine trying to be a country singer these days, having to put out content to show that you’re happy and you’re having fun, and that life's so great. They're dealing with pressures that we never had to deal with.

ESQ: I'm sure you saw Billboard just put out a list of the 20 biggest country artists of this century…

DB: Am I on the list? Did I make it, or am I number 21?

ESQ: You’re right there at number 20.

DB: OK, squeaking in there. I’m very, very appreciative, but I have zero overall cares about legacy or who thought what of me, other than the fans. The fan experience is everything I focus on—that and my kids, what number they'd have me ranked at. I think they'd have me at number one and that's the overall goal.

There's no gold records at the house, there's no indications that I'm, like, a top 20 artist in country music. My kids aren’t aware of that. They just know me as a dad that's always available, that says yes to whatever I'm being asked to do, whether it's play catch or put some toenail polish on and do the ballerina stuff, and there’s still a lot left to do with them before they're fully baked and out the door.

ESQ: You really don't think about your legacy?

I don't think about any of it. I've done all that stuff. If I don't get invited to the ACM awards, I'm like, man, I've had my time. I've been doing this 20-some odd years. I'm so happy with the younger generation coming up getting their shot to go do the whole thing and have their moment.

I don't hold onto anything in that realm at all. I just love playing music and I’m not planning on leaving anytime soon. We always get compared to NASCAR, and we’re lucky enough to be one of the cars that's not just getting out there so other cars can pass them. We’re one of the cars up front that's got a chance to win Daytona every year.