Dierks Bentley may be one of Country’s biggest stars today, but it took a lot of hard work, hustle, and even a season of being banned from the Opry to get there.

During his time on the Friday Night Takeover with Audacy’s Rob + Holly, Dierks shared a story from before he made it big when he took advantage of an opportunity at the Grand Ole Opry that ultimately got him banned for a bit.

“I used to work next door to the Grand Ole Opry at a place called TNN, The Nashville Network, which is also where CMT was,” Dierks shared of his early days in Nashville. ”There was little sheet you could sign on the way out that would put you on the backstage list for the Opry, so I always signed it. I’d get done with work and be able to walk right down to the Opry — see these great performers, you know?”

Spending every weekend at the Opry watching his heroes like Little Jimmy Dickens, Porter Wagner and The Osborne Brothers, was a dream come true for Bentley, but he got a harsh dose of reality when he was told to scale back.

“Pete Fisher, who was running the Opry at the time, he sent an email over to [my work]… he said ‘Love Dierks, great guy, but he can’t be over here every weekend — you gotta space it out a little bit.’ So, I kind of got my leash yanked a little bit,” he laughed.

The reality check didn’t break Dierks spirit, he found other ways to get involved and watch the greats by heading to Nashville’s famed Lower Broadway honky tonks and even securing an internship with CMA [Country Music Association] which got him even closer to the stars.

“I just wanted to be around it all the time,” he said of his love for Country music. “I actually worked as an intern for the CMA. The Opry house is where we used to have all the CMA Awards… I had the headset on, I was walking artists around backstage. I had a chance to walk Shania Twain from the stage to her tour bus, which was pretty cool. She was wearing like, the black, leather midriff stuff and I was like, ‘Wow! Country music is pretty cool!’” He laughed.

“I remember taking Jo Dee Messina to a Fan Fair back then,” he recalled. “I was driving her in a golf cart and she had the little, purple glasses she had when she first came out. She was like, ‘I don’t think anybody’s going to know who I am,’ we came around a corner and it was like [people screaming] ‘Jo Dee!’ And I was like, ‘I think you’re going to be OK.’”

Now, a superstar star in his own right, Dierks says he hasn’t shared those memories with Shania or Jo Dee — whom he now considers a friend as he sees her at the local hockey rink with her kids.

“Jo Dee— she’s a hockey mom, I’m a hockey dad… I see her at the rink sometimes. I don’t now if I’ve told her that story or not, now we’re like friends so it would maybe be kind of weird.” He continued, “Those early years were about just trying to find any sort of traction about Country music and how the industry works.”

Worked well for Dierks, who is still experiencing success more than 20 years into his career. One of his greatest accomplishments? Becoming a member of the Grand Ole Opry so he can visit whenever and however often he wants… no leash yanks.

Hear more about Dierks’ rise to the top, his new single, tour and so much more by checking out his entire conversation with Audacy’s Rob + Holly above.

Words by Monica Rivera Interview by Rob + Holly