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10 Things You May Not Know About Dierks Bentley

How many of these things did you know?

10 Things You May Not Know About Dierks Bentley
Dierks Bentley performs at Nissan Stadium on Saturday, June 8 during the 2019 CMA Music Festival in downtown Nashville. Photo courtesy of CMA

Dierks Bentley has been a constant hit maker in the country music world since his debut single “What Was I Thinkin’” hit radio airwaves in 2003. Since he’s been in the spotlight so long, it’s easy to think that we know everything about him, but there are still a few lesser-known facts about the singer. Here are 10 things you may not know about country mainstay Dierks Bentley.

  1. Dierks isn’t his real first name.

The first thing you learn about someone when you meet them is their name, and it may surprise some fans that Bentley’s legal first name is actually Frederick. Dierks is his middle name though, and he’s never been called anything different. He told Glamour in 2015, “My whole family goes by their middle name—my sister, my brother. So from day one, I’ve always been called Dierks. My mom was really upset when I named my son properly. I told her that his first name was actually going to be his first name! That’s how normal people do it, so I don’t know why she did it that way!”

2. He used to be in a band called the Uptown Ramblers.

Before Bentley was selling out amphitheaters and arenas all over the country as a solo act, he had another musical project in the 1990s: a band called the Uptown Ramblers. Dierks told CMT in 2012 that the group mostly played covers of ‘50s and ‘60s country songs. A flyer from one of the band’s gigs was displayed at Bentley’s 2016 Country Music Hall of Fame exhibit, Dierks Bentley: Every Mile A Memory.

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Happy Bday Cass! I love you (so does Doug…)

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3. He met his wife in eighth grade.

Bentley and his wife Cassidy, who has inspired countless songs and his 2016 album, Black, are middle school sweethearts! The two met in eighth grade in Arizona, and dated for a little while. They soon were separated by time and distance, but later reunited when Cassidy attended a George Strait show in Las Vegas where Dierks was the opening act. They eloped to Mexico in 2005 and now have three children together.

4. He spent many of his pre-famous days at a bluegrass venue in Nashville.

When Bentley first moved to Nashville, he was drawn to a small bluegrass venue called the Station Inn, which is located in the now-modern neighborhood of the Gulch. Bentley has often talked about how this venue shaped him as a young artist, and he’s certainly infused that bluegrass sound into his own music, especially with his all-bluegrass album, Up On The Ridge.

5. He has a mysterious first album called Don’t Leave Me In Love.

When country music fans think of Bentley’s first album, their minds most likely go to his 2003 self-titled debut on Capitol records that produced hits like “What Was I Thinkin,’” “How Am I Doin’” and more. However, as hardcore Bentley fans have found out, he has a mysterious first album called Don’t Leave Me In Love, which he released in 2001. You won’t find the album on any streaming services or in stores, but it can sometimes be found for sale online — for a hefty price, of course.

6. He’s a pilot.

Don’t worry — he wasn’t the one flying the plane in his 2014 hit, “Drunk On A Plane,” but in real life, Bentley does hold a private pilot’s license and owns a Cirrus SR22T plane. He has documented a few of his flying journeys on Instagram and often flies himself to and from shows.

7. He went to boarding school.

Bentley grew up in Arizona and went to school there for the first part of his life, but his parents later sent him to boarding school — first to Culver Academies in Indiana and then to the The Lawrenceville School in New Jersey. He once told The Press of Atlantic City that his parents sent him due to “troubles” in his adolescent years.

8. He attended the University of Vermont.

After graduating from high school in New Jersey, Bentley added another state to his list of residences by attending the University of Vermont. He only spent a year there before he moved to Nashville to attend Vanderbilt University. He graduated from Vanderbilt in 1997 and soon started his journey to becoming a country artist.

9. He was an intern at the Country Music Association.

Once Bentley moved to Nashville, he didn’t instantly become a star. He had a few gigs in the music industry prior to launching his music career, including interning for the Country Music Association. Bentley told USA Today that he attended and worked at CMA Fest back when it was called Fan Fair and held at the Tennessee State Fairgrounds. “I was running around with a headset,” he says of his internship. ”Jo Dee Messina was in the back of my golf cart, and I was taking her to booths.”

10. He has an alter-ego.

By now, most people probably know about Bentley’s alter ego, Douglas D. Douglason, lead singer of the ‘90s-inspired band, the Hot Country Knights. The band, made of of Bentley’s own band members, has been opening shows and playing sets for the past few years. However, the Hot Country Knights are turning out to be more than a fun cover band. They recently signed a real record deal and released their first single, “Pick Her Up,” featuring Travis Tritt. Be looking out for those guys on the radio!