Dierks Bentley has racked up a long list of live shows since the release of 'What Was I Thinkin' in 2003, and the 'Drunk on a Plane' singer is sharing the stories behind some of his favorites.

Two of his most memorable shows come off of his current Riser Tour, which kicked off in May with support from Chris YoungChase Rice and Jon Pardi. Bentley says he remembers the first show of the tour in Charlotte, N.C.

"I’ll never forget that first night out on our tour, looking around the corner at the crowd with [concert promoter] Brian O'Connell right before we went on and throwing back a shot," he tells Billboard. "To see all those people there when my name is at the top of the ticket will always be a photograph framed in my mind."

Bentley is averaging 16,879 tickets per night, and he recently added a second leg to the successful tour, which included a stop in his hometown of Phoenix.

"Headlining my hometown was incredible," he says. "There were over 17,000 people there, with my mom watching from here and my dad looking down from above. It was at the same amphitheater where I saw my first outdoor country show, which was Dwight Yoakam. It was a pretty full-circle moment for me."

Other memorable shows include playing at Bonnaroo for the first time in 2007, his show at Nashville's historic Ryman Auditorium for his bluegrass album 'Up On the Ridge' in 2010, and a performance at Colorado's Red Rocks Amphitheatre earlier this year.

"Someone had to be crazy to build an amphitheater in a small canyon, but thank God they did," Bentley says. "It's a spiritual thing for me, every time. It feels like all the other great artists who have played before you are right there in the rocks with you."

Bentley has worked hard and taken a sometimes unconventional path to success, but he says that he's enjoying where he's at now.

“I was hoping to get to this spot, but I sure took a roundabout way to get here,” he says. “It’s nice to be able to say that we put the music first, and when you do that, good things can happen far beyond what you could actually try to make happen.

"Sometimes you work so hard and pound your head against the door so long, and now I’m kinda not. I’m really enjoying it, and I think that shows on the stage," Bentley adds. "Something’s working, I don’t know what the hell it is, but I’m going to ride it for as long as I can.”