The Untold Truth About Dierks Bentley

Country music superstar Dierks Bentley has been topping the charts for years. He signed his first record deal 20 years ago, and since then he's been living his dream of making music and selling out shows. He's even managed to pursue other endeavors along the way.

The country artist has worked hard for his career, moving to Nashville at 19 years old to reach for stardom. And he's kept his work ethic along the way. "I knew if I was ever going to get to this place, there was only one way to do it," he said to the Tennessean of his work as an artist. The place he's gotten? Selling out shows to over 20,000 people, performing at the Grand Ole Opry, and opening for legends like George Strait.

Bentley is married and has kids, likes the outdoors, and likes beer, but you could figure all that out from listening to his music or scrolling through his Instagram. But what is there about him that you don't know? This is the untold truth of Dierks Bentley.

Dierks Bentley met his wife when they were both in middle school in Arizona, and he was immediately smitten. After years of having a crush on his longtime love, Cassidy Black, the two began dating when they were in high school, per The Boot.

"It's a pretty crazy story of just going back and forth with the right time or the wrong time, or right place, wrong time, all that stuff," Bentley told The Boot of his on-again-off-again romance with Black.

The couple split up when Bentley moved to Nashville after high school to pursue his music career, but he didn't give up on his love for Black. He pursued her as fervently as he pursued success in music, and luckily for him (and for country music fans), he ended up with both. We love a romantic story about high school sweethearts, and this one definitely doesn't disappoint.

As if their love story couldn't get more romantic, Dierks Bentley and his wife, Cassidy Black, married just days after he proposed. Bentley's love letters were clearly an effective tactic.

"I was playing a show in Las Vegas, and opening for George Strait, and she walked on the bus. I kind of knew that was the moment," Bentley told The Boot about when he knew his wife was the one. As Bentley can certainly attest, when you know, you know.

Soon after, the pair was engaged. The morning after their engagement, the two flew to Mexico, and days later they tied the knot. "We got married in a little chapel in Mexico, and it was beautiful and private and real," Cassidy Black told The Boot of her wedding with Bentley.

Bentley and his wife married in 2005 and have been together ever since. Of all the celebrity love stories, this one's got to be one of the sweetest.

If there's one thing almost all celebrities have in common, aside from being talented, it's venturing into the business world. Whether it's an endorsement deal for a commercial or an ad on Instagram, celebrities know how to make money. Dierks Bentley is no exception.

Bentley started his restaurant in Arizona, and it quickly grew to include two other locations across the United States, with a fourth opening soon. The eateries are called Dierks Bentley's Whiskey Row, and they serve award-winning food in an exciting environment. The eateries' vibe is all rock & roll, "inspired by Dierks himself," according to the website.

All of the locations are important places to Bentley, but the Nashville restaurant is particularly special to him. "It's really a full-circle moment for me to be opening Whiskey Row on this street," he told The Country Note about opening his gastropub on Broadway, as he used to play there, as have many other famous country acts. "It might possibly be a place where new artists could get their start," he said of his restaurant on the famed street.

Lots of celebrities fly private, but few actually fly private. And by that, we mean that few actually pilot the plane themselves. Dierks Bentley is the exception. According to Taste of Country, Bentley got his pilot's license in 1997. After his concerts, he frequently flies home on his private aircraft. 

Bentley is generous with his plane, too, often giving his band members rides home on it, even ones who were adamant against flying. "Once they got a taste of getting home, not having to be gone all the time ... they've all started flying with me," Bently told the National Business Aviation Association. He even upgraded to a bigger plane to accommodate more passengers.

Bentley is no stranger to turbulence as a pilot. On The Bobby Bones Show, he shared with the hosts that he once lost an engine while flying from Nashville to New York. He maintained he wasn't worried thanks to his training. We just hope that as a pilot, he's never "drunk on a plane."

We love when celebrities' kids share their parents' passions. Why else would we be so invested in North West and Blue Ivy? Dierks Bentley and his wife share three kids, two girls and a boy. His love for music and singing, like with many other celebrities, has apparently been passed on to his children. "All my kids love performing," Bentley told WIN 98.5.

Bentley's oldest is especially passionate about singing, and will perform with him on stage. "It's a special thing to get to share together," he said of taking the stage with his daughter Evie, who entertained fans at a concert, taking Elle King's part in her duet with Bentley, "Different For Girls." Bentley told Good Morning America he won't push anything on her, though. "I want her to just explore it on her own terms," he said. We love a supportive father.

Bentley is pushing one thing on his kids, though — taste. "I'm trying to help them with a playlist," he told E! News. "We love Lizzo and Dua Lipa and of course Maggie Rogers. They have a big influence on me too."

While becoming a bona fide country music superstar, Dierks Bentley lived in Nashville for 26 years, but amidst the COVID-19 pandemic, he and his family moved to Colorado, per E! News, joining many other Americans in a mass exodus to rural areas.

"I've wanted to move out there for a long time, so I kinda used it as an opportunity to sneak out there," he told Taste of Country of his migration west. And Bentley loves that he can be virtually anonymous while living in Colorado. "Nobody cares. Which is great, to have the ability to just go somewhere where you can be whoever you wanna be."

Bentley doesn't plan to remain in Colorado forever, though. He added that his children love Nashville, and he intends to return, but they're having fun for now. In fact, Denver, Colorado is the soon-to-open fourth location of his restaurant chain, Dierks Bentley's Whiskey Row — one more reason to visit Colorado.

Many celebrities use their resources to give back. Whether it's Rihanna hosting the Diamond Ball or Jennifer Aniston starring in commercials to raise awareness for St. Jude Children's Research Hospital, celebrities often aid worthy causes. Dierks Bentley is just as giving, hosting his own event. Bentley founded Miles & Music For Kids, a motorcycle ride that raises money for children's hospitals. And although the ride has been suspended for the time being, they raised $4 million in 10 years, per Sounds Like Nashville.

Bentley gives back in other ways, too. When the pandemic forced a worldwide shutdown, Bentley's restaurant workers were left without an income. To help out, he gave his restaurant employees bonuses to compensate, he shared in a tweet.

Bentley also continued paying his road staff, keeping 25 people on full salary throughout the shutdown. "I'm trying to take care of them through this time," he told E! News. That's the celebrity news we like to hear.

We know Hollywood and Nashville are full of ghost songwriters, but Dierks Bentley writes his own music. "I probably have written more songs on my albums than anyone I know, except maybe Taylor Swift," he told Taste of Country. If you know anything about Taylor Swift (if you don't, how's that rock you're living under?), you can surmise that Bentley's clearly written a lot of songs.

Bentley likes to write with many different people, too. "Maybe they've had hits, maybe they've not," he said of the fluid nature of his songwriting team. "Writing for me changes with every record."

That sentiment was certainly true for Bentley while writing his last album, "Make My World Go Black," as much if it had to be done via Zoom due to the pandemic. "I didn't even know what Zoom was until March and now I've used it a lot to write songs," he told E! News of his newfound use of the video communication platform.

Not only is Dierks Bentley a singer, songwriter, pilot, and restaurateur — he's now a fashion designer, too. Like many celebrities, Bentley took his personal style and turned it into a lucrative deal. He's once again giving us Rihanna vibes (Fenty, anyone?). Who knew they had so much in common?

The country music star joined forces with the menswear brand Flag & Anthem to design a lifestyle collection called Desert Son. "This has been such a fun thing to create and develop," Bentley told MR Magazine.

The line features clothing you might picture Bentley wearing himself, like flannel prints, distressed graphic tees, and button-downs. "I love clothes that are perfectly worn-in," he said of his fashion sense and added that he's "learned over the last few months that there's a real art to getting that just right." The collection has pieces available for men and women, according to their website. (BRB — browsing Desert Son for another WHF sweatshirt.)

It's a lot to expect musicians to drop unheard music completely out of the blue. Not everyone is Beyoncé, after all. But Dierks Bentley surprised fans on this tour by playing them an unheard single, "Beers on Me," per Country Now, which his fall tour is named after. The song is now available on all platforms.

Bentley wrote "Beers on Me" with other writers — a few industry staples and two new acts to the genre — Breland and HARDY — who were both included on the record. He loved working with the young songwriters on this project, saying, "it's just fun being around them — [seeing] the way they write, the way they operate, the way they work."

The song is "about the importance of just letting go," Bentley told People, adding that he'd "love at [his] live shows to buy every single person that is 21 years old a beer." We'd love that, too.

Dierks Bentley, like many celebrities, and some politicians, doesn't go by his first name. His given name? "It's Fredrick Dierks Bentley, but my whole family goes by their middle name — my sister, my brother. So from day one, I've always been called Dierks," he told Glamour.

Bentley added that the tradition runs so deeply in his family that his mother was upset when he didn't carry it on with his son. Actually, none of his kids go by their middle names. Evelyn Day, Jordan Catherine, and Knox are all called by their first names, unlike his immediate family growing up, per Country Fancast.

Bentley is in good company in Nashville when it comes to stars who don't use their real names. Luke Bryan, Tim McGraw, Faith Hill, and Shania Twain all go by different names than the ones they were born with. Even Bentley's hero, Hank Williams, changed his given name, Hiram King Williams, for his career, per Wide Open Country.

We all remember our first concert, right? Dierks Bentley certainly does. Bentley shared with co-anchors of the Today show that his first concert wasn't country, it was rock — Bon Jovi and Skid Row.

Even though his first concert wasn't country music, he's always loved it, and he added that his dad's taste in music had a huge impact on him. "We always drove around listening to country radio — George Strait and Hank Williams and Randy Travis," he told Taste of Country. "Without him I wouldn't be doing this, for sure," he added.

Although Bentley looks to many other musicians for influence, his biggest inspiration for his music is his own life. He noted to The Guardian that his "first record was all about the musicians," but that a "transformation happens when a young artist goes on the road," noting that his second album reflected that, and his succeeding albums have continued reflecting his life and where he's at. "I think it's always evolving."

Everyone starts somewhere. Justin Timberlake and Britney Spears started in The Mickey Mouse Club. Dierks Bentley started in Uptown Ramblers, a band he was part of in the '90s, per CMT News. "We didn't do the hits. We didn't do anything current, just '50s and '60s country," he said of the former cover band.

Bentley's current band is called Hot Country Knights, a parody group. In a piece titled "Riding 'The Mullet to Success,'" NPR wrote that the band was inept and unprofessional, adding that they acted like it was the year 1992 and they'd stepped "right out of some country bar." Which is exactly what the group is going for.

And they're a little more legitimate than Uptown Ramblers. Bentley's parody band has signed a record deal with Universal Music Group Nashville, per Variety, noting we have yet to see whether they'll release original music or stick to covers. "It's what we look forward to more than anything else, honestly," Bentley said of performing with the band.

Through his music and various business ventures, Dierks Bentley has accumulated a $30 million net worth, according to Celebrity Net Worth. His restaurants, recording deals, tours, and collaboration with Flag & Anthem have all been worthy enterprises, financially speaking.

Bentley's financial success all stems from his incredible music career, though. The country music star has had 27 songs on the Billboard Hot 100 chart and 11 albums on the Billboard 200 chart, per Billboard. Thanks to hits like "Drunk On a Plane," "Somewhere On a Beach," and "What Was I Thinkin'," Bentley is doing quite well.

Despite his massive success, family is the most important thing in his life, and he makes sure to spend as much time as he can with his wife and kids. He told The Boot, "one of the things I'm most grateful for is some of the success coming later as it has, because it's really nice to share it with somebody."