October 01, 2015 08:15 PM

Different hair, same dog.

Dierks Bentley celebrated a decade as a member of the Grand Ole Opry this week, bringing his steady sidekick – pup Jake – on stage for a victory lap. It was a fitting tribute given that Jake was also by the singer’s side in 2005 when Bentley was first inducted into the famed country music club.

“It’s pretty surreal how fast the last 10 years have gone,” Bentley told PEOPLE before taking the stage as the closing act of Tuesday night’s Opry. “It feels like it was just Oct. 1, 2005 and I was here with Jake being inducted.”

With his dog dutifully perched on his lap, Bentley, 39, marveled that “I still have Jake” but jokes that his pup’s “hearing isn’t what it used to be.” PEOPLE Country’s reigning Hottest Guy then proved his point by playfully calling Jake’s name – with no reaction from man’s best friend.

Dierks Bentley and Jake in 2005; Dierks Bentley and Jake in 2015
Chris Hollo/Hollo Photographics Inc.

Bentley, who recently wrapped his “Sounds of Summer” tour and joined Taylor Swift (yes Dierks, we spotted that T.S. 1989 bracelet on your wrist!) on stage in Kansas City to perform “Every Mile a Memory,” remains grounded and grateful for his success.

Playing the Opry was such a big dream for me,” Bentley tells PEOPLE, reflecting on the days before he was a country superstar. “Becoming a member of the Opry is beyond the scope of anything I could have ever imagined.”

“Ten years – that’s crazy,” Bentley told the crowd before launching into his biggest hits. The “Drunk on a Plane” singer, who left the pilot from Riser Air at home, treated the audience to a song from each of his six studio albums, including his first No. 1, “What Was I Thinking,” from debut album Dierks Bentley, as well as his current single, “Riser.”

The musician, who’s nominated for Best Male Vocalist at the upcoming CMA Awards, will also be celebrating the 10th anniversary of his Miles and Music for Kids charity motorcycle ride and concert that benefits the Children’s Hospital at Vanderbilt on Nov. 1. Florida Georgia Line, Thomas Rhett, Cole Swindell, The Cadillac Three and more country music artists will be joining Bentley for the annual affair.

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