Dierks Bentley Dishes on His Bumpy Road to Stardom: 'I Didn't See It Working Out for Me'

Austin Hargrave
Dierks Bentley photographed on June 24, 2015 at The Land Trust for Tennessee’s Glen Leven Farm. 

By mixing bro-pleasing songs about carousing and boozing with more sober lamentations on fatherhood and death, "country's hottest guy" has -- finally -- grown into a bona fide star.

"My career has been like that ramp," Dierks Bentley says, crossing a dirt parking lot as he leaves a Billboard photo shoot. He nods in the direction of a long loading ramp that slopes up from the mud onto the rear of a flatbed truck. The simile isn't entirely accurate -- his career arc has included a precipitous dip in the middle -- but the idea of a gradual climb holds true for Bentley, a tortoise among hares.

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He climbs into his own truck, a junkyard Chevy that appears to be white underneath the layers of dirt. His former blond curls have been shorn to a semi-mohawk that's in danger of becoming a mullet. People magazine recently named the green-eyed 39-year-old "Country's Hottest Guy," which he has turned into a punchline: He likes to board his tour bus and announce to his band, "Country's hottest guy is looking for a Porta-Potty."

He rolls down a window -- like most of the truck, the AC is busted -- and drives across Nashville to a favorite lunch spot: Arnold's, a family-run meat-and-three cafeteria where the owners greet him like a favorite cousin. Soon after we sit down, complimentary orders of hush puppies and peach pie arrive. "We're going to need a wheelchair to get out of here," he groans.

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Bentley moved to Nashville in that same Chevy, driving from Arizona with his dad. The business quickly turned him off. "I didn't see it ever working out for me. I don't wear tight, starched jeans. I don't have a big belt buckle and a cowboy hat. And I've got a weird name." (It rhymes with "jerks.")

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Bentley began going to bluegrass shows at The Station Inn, which in turn made him excited about country music from the '50s and '60s. His passion for the era culminated in his memorable major-label debut in 2003, "What Was I Thinkin'," a romping song with banjo and Dobro about a night of dangerous ­adventure with "a beauty from South Alabama," and the first of his 13 No. 1 Hot Country Songs hits. "He could've become a one-hit wonder," says Luke Bryan. "Dierks has been probably the only ­artist to actually outdo that first hit."

He quickly established himself as a first-rate singer of songs about beer, and as a wit: "Garth [Brooks] made fans cry and laugh at the same time," he told CMT in 2004. "I want them to cry, laugh and throw up all at once."

Plenty more beer songs followed, and in 2009, another signature hit, "Sideways," a celebration of hanging out in bars. "It's a ridiculous song," Bentley said when this writer interviewed him that year. "Not a lot of synapses firing on this one."

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Around that time, he now says, "I was really burned out." He was opening for Brad Paisley, one of several newer singers who had pushed past Bentley in their ascent. He and his wife, Cassidy, had a baby who was less than a year old. Bentley was trying to become a headliner, and it wasn't working. And Nashville was now full of guys doing songs about beer and pretty girls.

He returned a second time to his refuge and made a bluegrass album, Up on the Ridge, which had no fewer than zero hit singles. "People thought I was crazy," he says. The slope of his career ascent hit a sudden drop.

While Bentley was working on Riser, one of the best country albums of 2014 and a follow-up to the party-crazy record Home, he nearly left off "Drunk on a Plane," which has become his best-known song. It didn't seem to fit with the rest of Riser, some of which addressed two recent events: the birth of his first son, Knox (he has three kids in all), and the death of his father, Leon, which Bentley wrote about in "Here on Earth."

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"I sent the song to Bono" -- a fan and friend -- "and said, 'It's a little rough,' " recalls Bentley. "He wrote me back and said, 'It's not rough. It's a polished gem.' "

Bentley describes his dad as a fun-loving guy who loved beer -- qualities evident in his son. He realized that making an album without fun songs wouldn't fully depict his life, so "Drunk" went back in. In a way, it's as personal a song as "Here on Earth": "I've been drunk on plenty of planes," he says.

This summer, right alongside Paisley and Bryan, he topped the bill at New York's ­inaugural Farmborough festival, and he's ­touring sheds, an established headliner at last. DJs know how to pronounce his weird name, just as they'd learned to say "Wynonna" and "Shania." It took seven albums, but he figured out how to be a headliner: Sing your life, the bad parts and the good. "I have these songs I can relate to, because they're all a piece of my life. Maybe that's why I've never had a bad show." He reconsiders. "Or maybe it's the alcohol."

This story originally appeared in the Aug. 1 issue of Billboard.