Dierks Bentley: The Struggles Made Him Stronger

The Lows and Highs of His Country Career So Far

What doesn’t kill you — or crush your intensely sensitive ego — makes you stronger. And Dierks Bentley is proof of that.

On Monday (Feb. 5), the first day of the annual Country Radio Seminar, Bentley shared some of his stories with the country music industry crowd. And within those stories, he revealed some of the defining moments and humbling experiences that made him the artist he is today. In other words, it hasn’t been all sunshine and rainbows.

Bentley took the audience all the way back to the early days when he was initially content to be playing in bars and clubs with Cross Canadian Ragweed and Stoney LaRue. But then he wanted more.

“I was all about making a fan one handshake or one beer at a time, and playing those rock bars and clubs,” Bentley said, adding that he was then invited to be the opener on a couple of arena tours. “I’d done George Strait and Chesney, so what else was there to do? I was enjoying where I was. It was a big party. But what happened for me is we started getting into arenas at the end of 2006.

“I got into these arenas, and I remember walking into The Palace in Auburn Heights in Detroit, and the place holds 20,000 people. And we’re playing for like 2,500 people. After two years of kind of banging my head against the wall trying to make that work, you realize then you’re either moving in one direction or another. You can’t play clubs for the rest of your life. That’s just not the case.”

He recalled how critics would come and review the show and write things like, “God bless Dierks, he sang like it was a sold-out building, but only about 2,000 people were there.”

Bentley even faced a personal obstacle right out of the gate, when he released his debut single to radio. His hometown country radio station wouldn’t play it. “When you’re a new artist, and you release a song, it feels so good. But one of my hometown stations in Arizona wouldn’t play it right away. How could they do this to me,” was what he was thinking. “I couldn’t believe they wouldn’t play it the first week, the second week.

“What I learned is that, man, you are not the only one. You get so caught up in your own little world. Just because they don’t play your song doesn’t mean they don’t like you or don’t like the song. You learn to separate your feelings. Music is so personal, but at the same time, there’s the business part that is a big part of it, too.”

Later on in Bentley’s career, he said, when you would think that any new release would be an automatic add on country radio, he sent “Bourbon in Kentucky” — his 2013 collaboration with then newcomer Kacey Musgraves — to radio. “I was playing Stagecoach, and I got a call, and we were just going over songs. And ’Bourbon in Kentucky’ was really cool, so it was like, ’Let’s lead with that.’ It was summertime, and I just remember listening to Florida Georgia Line on the radio. And their music’s so fun. And then ’Bourbon in Kentucky’ comes on, and it’s like a funeral. It was not fun at all. It was like a train: getting it loaded up and the coal and it’s a slow start, and you’re pushing it, and then to have to stop that train and then pull it back and release another single. That’s a hard thing to do.”

The train stopped when the song peaked at No. 45 on the charts. But being the eternal optimist that he is, Bentley told the CRS crowd what that cloud’s silver lining was. “’I Hold On’ might not have even a single if ’Bourbon’ had worked out,” he said.

Bentley’s Q&A at CRS followed the presentation of his 2018 Artist Humanitarian Award. He was honored for all he’s given back through his charitable initiatives and events. Bentley has raised more than $4 million for children’s charities through his Miles & Music For Kids motorcycle ride and concert, and more than half a million dollars for the families of the Granite Mountain Hotshots with his Country Cares Concert in Arizona.

Alison makes her living loving country music. She's based in Chicago, but she's always leaving her heart in Nashville.