By 19, he was off to Nashville.
"That's all I knew about country music. As far as I knew, Nashville was the place to be if you want to make country music? I didn't have a whole lot of skill at the time. I could barely sing and play at the same time. I really had to learn, and I knew that coming into it. I moved to Nashville with an open mind to study and learn and try to get better."
"You have a dream that burns so badly that the decision is made for you. It's like a disease. Fortunately, I didn't have to make too many decisions."
He received support from his parents, his banker father and his mother, a housewife. "My mom's the kind of person that says follow your heart, and I've always done that."
When Bentley got to Nashville, he hit the bars and clubs, including haunts like Springwater and the Market Street Brewery where he got good enough to give up the pay of free draft beer for greenbacks.
Bentley also worked at The Nashville Network back when it used to be about country music. He searched through old music footage in the tape library for a documentary.
Bentley reached the point where he wanted to put out his own album. "Don't Leave Me In Love" came out in 2001. (The disc is now out of print, although Bentley says he will reissue it at some point).
About the same time that Bentley released an album on his own, he got a publishing deal with Sony writing songs. A song plugger there (pluggers pitch songs to singers to record) matched Bentley and Beavers, who also was writing at Sony.
Bentley says that what attracted him to Beavers was that he "kind of discovered we liked the both kind of country music. As soon as we started writing songs together, I knew he had the same kind of musical vision that I did."
Beavers says what makes writing combos work is "one of the things you can never figure it out, why it works with some people...I met him, and I really liked him. Within 15 minutes of sitting around and talking, I could tell...His idea of real country music was George Jones and Buck Owens, not someone of the '90s. We hit it off immediately."
Bentley and Beavers hit the recording studio to record demos, which ended up being passed onto record companies. A few became interested, and Bentley liked what he heard from Capitol.
Part of the deal for Bentley was that Beavers was going to produce him even though he only had done demos and "smaller things because it was kind of a first time for both of us," Bentley says.
Record companies tend to want someone tried and true at the production reins, and given that Bentley was an unknown artist, he was given a lot of freedom.
But why did Bentley want Beavers?
"You got to trust your instincts," he says. "I'd been in Nashville long enough. I'd already made a record on my own. I knew what worked for me. It felt right for me. Working with Brett felt like the right guy to work with."
"The first record made me know what I wanted to do. When I made a record deal, I knew I was going to stick to my guns," he says.
"From day one, they knew that I would be writing most of the songs. They knew Brett Beavers would be producing the record. They knew that was the only way I would sign with them."
Beavers says he "was definitely very concerned about doing a really good job. I knew this guy Dierks finally got his shot on a great label...I did not want to screw it up...Going in, I was feeling my way around a little bit."
The self-titled Capitol debut came out in 2003.
Bentley had a hit out of the box with "What Was I Thinkin'," a fast-paced, funny number about hooking up with a girl from an oddball family.
But don't give Bentley any credit for choosing the song to be his introduction to country fans. If Bentley had his druthers, he would have picked the ballad "Wish It Would Break."
Fortunately, Capitol Nashville did not listen to Bentley.
Bentley also scored a hit with another revved up song, "How Am I Doin'."
And he hit the road - hard - playing about 300 dates after the album was released.
"We're a real touring band. We really do build up our following with touring...We haven't done the Tonight show (though that actually is slated for mid-May). We make a fan one handshake at a time."
Bentley clearly is jazzed about "Modern Day Drifter."
Based on the lyrics, Bentley doesn't seem like he wants to be tied down. On "Lot of Leavin' Left to Do," which he wrote with Beavers and Deric Ruttan (they also wrote "What Was I Thinkin'" together), Bentley sings "Guess the Lord made me hard to handle/So lovin' me might be a long shot gamble."
But Bentley turns around and gets sensual on "Come a Little Closer" where he sings "we'll steal away/Off into the night 'til we make things right/The sun's gonna rise on a better day."
Referring to "Lot of Leavin'," Bentley says, "That song really sums up where I am in my life right now not only musically, but personally. It's hard to have a relationship with a girl when you're leaving town every night. When I do back to Nashville, I don't even have a house. I have a hotel room. Hopefully, there'll be a time when I settle down a little bit and have a regular schedule like everybody else does."