Dierks Bentley had just released the song that would launch him into overnight stardom when he made his debut on the Grand Ole Opry on April 18, 2003.

Bentley performed his debut single, "What Was I Thinkin',' during his first-ever performance on the hallowed stage of the country music institution.

According to the Opry's website, the song was actually inspired by a girl Bentley had met backstage at the Opry long before he was signed to a label deal. He was working a day job at the Nashville Network, which was located on the grounds of Opryland where the Opry House also resided, and Bentley would stay late on weekends and slip into the backstage at the Opry to hang around and visit with the musicians.

He did it so many times that Opry management had to start banning him, but Bentley got the last laugh when Opry fixture Ricky Skaggs personally introduced him at his debut performance.

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"I just want to add my name to the list of people that said this was the biggest night of their life, because this really is a dream come true," Bentley told the audience.

"What Was I Thinkin'" reached No. 1 on Billboard's Hot Country Songs chart in September of 2003, launching Bentley on a career path that would see him become one of the most consistent hitmakers of his generation. He was inducted into the Opry two years after his debut, and performing there remains an important part of his career.

"I actually come to the Opry even when I'm not playing," Bentley says. "I just come out because there's always great music."

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26 Country Stars You Won't Believe Aren't Grand Ole Opry Members

Fifteen living CMA or ACM Entertainers of the Year are not members of the Grand Ole Opry, and a few of them barely recognize the vaunted stage. George Strait, Kenny Chesney and Willie Nelson are three legends who rarely play the Grand Ole Opry. Why?

That answer is often difficult to determine, but this list suggests reasons where appropriate. Membership into the Grand Ole Opry comes with an obligation to play the show frequently, but that's often set aside (Barbara Mandrell is an inactive member, for example). Only living artists are considered, and once a member dies, they are no longer a member.

As of 2023, there are more than 70 members of the Grand Ole Opry. Historically, nearly 250 men, women and groups were members — so, it's a select group that excludes several Country Music Hall of Famers.

Gallery Credit: Billy Dukes

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