It’s hard to even imagine the Grand Ole Opry without Brad Paisley, so great has been his contribution to the country music institution. But on May 28, 1999, the then 26-year-old artist was just another country newcomer making his debut on the hallowed stage of the Opry.

Paisley’s debut performance on the Opry stage came just days before the release of his debut album, Who Needs Pictures, which dropped on June 1, 1999. His debut single, the album’s title track, had been in release since February, so Paisley was not entirely unknown when he hit the stage in Nashville for what would turn out to be one of the most important gigs of his life.

Opry legend Little Jimmy Dickens was one of Paisley’s heroes, and he followed Paisley’s performance that evening. As Paisley recalled to Nashville’s Tennessean newspaper, the mostly unknown singer mustered up the courage to approach Dickens backstage and ask him to go fishing, which he agreed to do, sparking a friendship that would last until the end of Dickens’ life in 2015.

As Paisley progressed from newcomer to hitmaker to one of the biggest stars in country music and co-host of the CMA Awards, Dickens often appeared in CMA skits as comic relief for his good friend.

It didn’t take long for the rest of the Opry family to appreciate Paisley’s talents, either. Dickens, Bill Anderson and Jeannie Seely asked him to join the Opry on Dec. 16, 2000, just a year-and-a-half after his debut. By that time, he had performed at the Grand Ole Opry 36 times. Paisley was inducted into the Opry on Feb. 17, 2001, and it’s still one of his favorite gigs to play.

“I love the Opry. I would call it my favorite place in the city of Nashville,” Paisley says. “That hallowed place that feels like home that has accepted me from the beginning.”

The Best Guitarists in Country Music