Dierks Bentley on His Success: 'I Don't Know How the Hell I'm Here'

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Dierks Bentley performs on stage on Day1 of the C2C Music Festival at O2 Arena on March 15, 2014 in London, United Kingdom.

“What are all these people doing here?” Dierks Bentley wonders as he looks out at the rapidly filling lawn at the Verizon Amphitheatre in St. Louis. “Don’t they know this is an almost 40 year-old married guy with three kids?” 

Bentley, 38, will take the stage in about three hours on this steamy Sunday night in late July, and country music fans are indeed pouring in to see him. St. Louis is the latest in a run of “best nights of your life” that keep stacking up for the singer this year. Fueled by of one of the biggest hits of the summer in “Drunk on a Plane,” Bentley finally finds his name at the top of the marquee more than a decade into his career. “From a headliner development point of view, the success story of the year is Dierks Bentley,” Brian O’Connell, president of Live Nation's country touring division, told Billboard earlier this year. “He is selling a ton of tickets, [and] I’m so happy for him and his whole team. He deserves this.”

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Bentley has certainly paid his dues, starting like so many other country acts by playing for tips down on Nashville’s Lower Broadway. He has taken an unconventional path to stardom, dating back to his out-of-the-box hit “What Was I Thinkin’” on Capitol Nashville in 2003. While most artists rarely veer from playing festivals, fairs and supporting bigger stars as they work their way up the ladder, Bentley took risks and followed his muse, most recently by stepping off the mainstream country grid in cutting a bluegrass album, Up on the Ridge, in 2010.

Now, Bentley is a bona fide star, averaging 16,879 tickets per night, according to data provided by management, with support from Chris Young, Chase Rice and Jon Pardi. “I was hoping to get to this spot, but I sure took a roundabout way to get here,” Bentley tells Billboard backstage before the St. Louis show, clad in a faded Blue Oyster Cult T-shirt, jeans, worn biker boots and a Stubb’s BBQ ball cap. “It’s nice to be able to say that we put the music first, and when you do that, good things can happen far beyond what you could actually try to make happen.”

That includes headlining. Though he has co-headlined twice with Miranda Lambert, this is the first summer for Bentley to go out on his own to the large venues, a career milestone for any artist. “I was trying to make headlining happen, and sometimes you can’t do that just through work, you have to let the music steer the way,” he says, then ponders that thought. “I guess. I don’t know how the hell I’m here, really, but something’s happening. Ten years into my career, I’m headlining these places, but I wouldn’t have it any other way, man. It’s been a great climb. A slow climb.”

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Bentley realized he was taking a huge risk when he made the bluegrass record, but he says he felt like he was stuck in place on the mainstream country track. “I knew I was walking away from an easier road, but that road wasn’t taking me where I wanted to go,” he explains. “So I just made the decision to step away and make a record going back to my roots and how I started, kinda getting off the grid and see what happens.”

Bentley followed Ridge with Home in 2012, and then this year’s Riser, a deeply personal album influenced by the life-altering experiences of the death of his father and the birth of his son that has moved nearly 200,000 units in the U.S., and spurred 1.5 million in digital track sales. Bentley’s live shows are marked by an insane reception to that album’s “Drunk On A Plane,” an unqualified smash: It's been on the Billboard Hot Country Songs chart for 16 weeks (and counting) and notching 675,000 downloads. The singer's Funny Or Die video has taken on a life of its own, and exposed Bentley to a new audience, and one could assume many of those fans are checking out Bentley for the first time on this tour. Watch the clip below: 

But it appears that most of the fans in attendance have been along for the whole ride, and they’re chugging down “Drunk On A Plane.” “I didn’t even know if I wanted that song to be on the album,” he says, “and I didn’t think it should be the next single. And as soon as it comes out, it’s, ‘Why would you want that to be a single? People love that song.’”

Then again, Bentley admits he might not be the best at judging the commercial marketplace. “I don’t know that very well. I know this,” he says, gesturing toward the touring world around him. “This is what I’ve spent 15 years working on, being in front of these people.”

“These people” are completely enamored of “Plane,” and Bentley and his team have the unique pleasure of watching a song blow up in real time as he takes it to venues across America. The song has changed positions in the set list as it climbs the chart. “It started off like fourth in the set list, then we moved it down to about sixth, then eighth, and now it’s down pretty far towards the bottom,” he says. “It could be the bottom if I wanted it to be, it’s that big of a song. There’s a difference between a No. 1 and a Number One.”

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Bentley has reconciled the double lives of family man and touring artist, and believes now that the former improves the latter. “When I was single and drinking Jager bombs, I was focused entirely on the show and I didn’t think you could be married and have kids and have great shows, because you’re splitting your attention,” he says. “Now I tell the guys, ‘We’ve been here in this parking lot for 20 hours. My wife misses me, my kids miss me, I’m missing them. We need to pour everything we’ve got into this show tonight to make this day of sacrifice worthwhile. If we don’t, what the hell are we doing here? Just getting older, and we’re getting older away from them. We have to kill this show.'”

A prayer and a chant, and the band takes the stage. All ragged ringmaster, Bentley, wearing a T-shirt and ripped jeans, would not stand out at all in this crowd of mostly 20-somethings were he not the star attraction. Tight and and on point, he and his band charge through well-received party anthems like “5150” and “Tip It Back,” and a rumbling “Not a Lot of Leavin’ Left to Do,” and the crowd sings along rapturously to a galloping “Free And Easy (Down the Road I Go),” “Every Mile a Memory,” and the pulsing “Come a Little Closer.” Every bit the life of the party, Bentley pulls a fan on stage for a beer shotgunning competition (Bentley wins), then shifts gears with power-charged “Up on the Ridge,” which becomes a spooky barnburner in this electrified configuration. That song leads to a real musical moment when the band heads out to the B stage for sing-along on Bon Jovi’s “Livin’ on a Prayer” in tribute to Bentley’s first amphitheater experience.

By the time “Drunk on a Plane” rolls around, the crowd is going wild, and Bentley lifts more fans in flight attendant and pilot garb up on the stage to take a turn at the mic. They, as do the rest of the crowd, know every word, and this is what a big ol’ hit looks like. Reality or not, Bentley comes across as one of them, as if only a few chords and a bit of luck stood between him and the crowd.

But, as with most stars, talent and hard work are the difference makers, even if this mid-career surge is a bit puzzling to the artist, given he has tried to back off over-thinking every detail. “I don’t know what the hell is going on,” Bentley repeats backstage, “but this seems to be working. Sometimes you work so hard and pound your head against the door so long, and now I’m kinda not. I’m really enjoying it, and I think that shows on the stage. Something’s working, I don’t know what the hell it is, but I’m going to ride it for as long as I can.”

DIERKS BENTLEY'S MOST MEMORABLE SHOWS

1. Hometown Phoenix Show of Riser Tour (July 2014)
"Headlining my hometown was incredible. There were over 17,000 people there, with my mom watching from here and my dad looking down from above. It was at the same amphitheater where I saw my first outdoor country show, which was Dwight Yoakam. It was a pretty full-circle moment for me."

2. Playing Bonnaroo for the First Time (June 2007)
"Up to this moment, I had always felt like we drew fans from all genres, but this gig was a physical test of that theory. Having Sam Bush and Buddy Miller join us for a of couple songs sealed our 'roo moment."

3. Bluegrass Show at the Ryman for Up On the Ridge (May 2010)
Up On the Ridge was a return-to-my-roots type record, and the Ryman is part of the physical foundation of country music. I was collaborating with Chris Thile and the Punch Brothers and, later, the one and only Del McCoury. Even Ketch [Secor] from Old Crow Medicine Show got up for the finale. It was a big night for a kid who used to run his hands along the bricks of the Ryman back in the honky-tonk days and dreamed of playing it." 

4. Pre-Grammy show at Troubador in Los Angeles with Surprise Guests Miranda Lambert, Blake Shelton, Black Keys, Zac Brown and Del McCoury (February 2011)
"It was a legendary rock bar that Nashville took over for the night, and it was awesome. I had done this once before with Dwight Yoakam, Mike McCready of Pearl Jam, and Hayley [Williams] of Paramore. But this time we included our country friends, as well as Nashville transplant Dan Auerbach of The Black Keys."

5. Red Rocks Amphitheatre Show, Morrison, Colo. (2014)
"Someone had to be crazy to build an amphitheater in a small canyon, but thank God they did. It's a spiritual thing for me, every time. It feels like all the other great artists who have played before you are right there in the rocks with you."

6. The First Night of the Riser Tour (2014)
"I’ll never forget that first night out on our tour, looking around the corner at the crowd with [concert promoter] Brian O'Connell right before we went on and throwing back a shot. To see all those people there when my name is at the top of the ticket will always be a photograph framed in my mind."