“I’ll show you this,” says country music superstar Dierks Bentley as he walks me through his Nashville home to his bedroom closet. When we arrive in his bedroom, he holds up a gray and white check-print flannel shirt. In his closet, he shows off more.
He’s not wearing a flannel right now but a green, short-sleeved T-shirt with Skiv in black, capital letters. I can’t tell if it’s in reference to the dungeon-crawling role-playing game on Steam, the London-based rock band, or the British slang word for “sovereign.”
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Bentley isn’t just a member of the Grand Ole Opry—the very place he was once kicked out of when he was younger. Nor is he just a three-time CMA Award winner, or a 15-time Grammy nominee with 22 No. 1 songs and eight billion streams. No, Bentley is also a bit of an entrepreneur. Besides his Row 94 Kentucky Straight Bourbon brand and his chain of Dierks Bentley’s Whiskey Row country bars in Arizona, Colorado, and Tennessee, he also has a clothing line with Flag & Anthem.
“That’s another thing I jumped into,” he tells me. “I didn’t mean to, but these guys found me on the road. They were like, ‘We love what you wear and we want to get involved with you.’”
Talking to Bentley is like talking to a friend. He’s present and enthusiastic and personable; traits that have helped build his legion of fans over his more than two decade-long career.
Originally from Phoenix, Arizona, Bentley remembers hearing Van Halen for the first time when he was 13 years old. “It kind of blew my mind,” he says. It wasn’t until he was 17 that he began getting into country music.
Dierks moved to Nashville in 1994 to attend Vanderbilt University and discovered a bar called the Station Inn. “Seeing a bunch of guys my age, wearing whatever they were wearing that day, walk in and walk up on stage wearing the same clothes…they weren’t dressed for showtime,” he says. “And they were just playing the crap out of these instruments and singing and harmonizing and laughing. I think that’s what made me want to really try to get better at playing the guitar.”
He decided to pursue a country music career. Since then, the “Drunk On A Plane” singer has released nine studio albums, his most recent, 2023’s Gravel & Gold.
Now, he’s at work on his 10th album and gearing up for his summer tour, which launches on May 29 in Austin, Texas.
On Valentine’s Day, Dierks released a new single, “She Hates Me,” a sort of comedic anti-love anthem about a vengeful ex-girlfriend. “It’s one of those songs that wasn’t really even meant to be written,” he says. He had been working on some other songs with longtime collaborators Ashley Gorley, Chase McGill, and Ross Copperman. But they started fooling around on their guitars, making each other laugh, and the single was born.
Between his music career, his business ventures, and his family, Dierks is a busy man. “People talk about retirement and stuff, or you have to take a break. And I always think, well if I’m getting to do what I want to do, with who I want to do it with, when I want to do it, why would I ever stop?”
Here’s a day in the life of Dierks Bentley.
Date 2/12/2025
Time I woke up I didn’t wake up today until 6:30. It was 5:30 yesterday for my son’s hockey practice. But today was a nice little sleep-in.
Every day starts with A cold plunge. I went out this morning and walked straight into it. I’m not usually in the best spirits in the morning but a little cold water and I chirp right up a little bit.
Breakfast consists of Coffee…black coffee. That’s it.
To get going I always listen to I’ve got to be honest, I love Frank Sinatra. Put on a little Frank and just ease into the morning.
I don’t feel dressed without A good flannel, preferably from Flag and Anthem.
Before I start working I must A morning workout class is the key to my mental morning health.
Currently working on A new record. Yeah, it’s going to come out this June. I was just in the studio today with John Anderson. Really fun. That, and just putting together the tour for the summer.
But I’d really love to be Hanging out with my buddies out in Colorado, doing a little outdoor adventuring, whether it’s some pond hockey or some skiing. I love this. You know, I love the winter. It’s oddly my favorite time of the year, and I just love being outside doing stuff in it. So anywhere just in the mountains is where I’d usually prefer to be.
Book I’m reading I just finished a great book, Long Island Compromise. I’m reading a book called The Hunter right now.
I don’t know how anyone ever… I hate social media, so this is my answer to that question. Hopefully, our kids one day will look back and go, “I don’t know how my parents’ generation lived that way, connected to an iPhone and always on social media.”
If I had to play one album on repeat, it would be How about the Del McCurry band? Cold Hard Facts,1996. That’s a good album.
The perfect midday consists of What I did yesterday. I do it every Tuesday. I play pickup hockey with some ex-pros and some up-and-coming kids, and some people like me who shouldn’t be out there. But it’s the perfect once-a-week midday thing.
To help get through the day Music to regulate my emotions.
Not a day goes by without speaking to Gosh, my wife. I mean, not an hour goes by. We’ve been together for 20 years and there’s not a single day that goes by that I don’t talk to her.
My daydreams consist of An empty schedule. I mean, there’s nothing better than seeing somewhere where you go, “Oh my gosh, I have nothing going on that day. Wow!” Those days when you’ve got nothing on the schedule.
I’ll always fight for Is it weird to say you always fight for your kids? I’ll do whatever it takes to try to help those guys out.
Currently in love with Tennessee. I’ve lived here for 30 years, and there’s been times I wanted to be back out West. You kind of have a love-hate relationship with it over the years of being here. But I just really love Tennessee.
Hoping to make time to watch I know there are some new shows out there, but I don’t know. I don’t know.
By my bedside I always have Earplugs. I found out early on that earplugs are the key. It’s kind of a weird thing to have as a parent in the house. But just a little blockage between me and the noise of the house.
To help get through the night Trazodone sleep gummies.
When I think about tomorrow I’m usually pretty stoked. I love what I get to do for a living. I love playing live music. I love my band, and my crew. I wake up thinking about tomorrow… another chance to do something that I love to do so much.
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