Josh Ross Talks Meeting Dierks Bentley And The Lessons He’s Learned From Jelly Roll

Growing up, Josh Ross says Dierks Bentley was one of the artists who first sparked his love for music. When he finally had the chance to meet Bentley, Ross wasn’t sure what to expect, but the experience turned out to leave a lasting impression on him.

In a recent conversation with Country Now, the Canadian singer/songwriter revealed that Bentely was one of the first artists who’s concerts he attended in Hamilton, Ontario. Even though he’s since established himself as a rising star in Music City, it wasn’t until earlier this year that the pair finally to meet.

Back in February, both acts were slotted to perform at the Universal Music Group (UMG) “Team UMG at the Ryman” luncheon during Country Radio Seminar (CRS) 2025. Knowing that Bentley would be backstage for the industry event, Ross took the opportunity to meet the artist that made a strong impact on him at an early age.

“So Dierks for me was one of the…I don’t always want to meet the people that I admire so much, but he’s somebody that came through and is exactly who was hoping he would be,” Ross said of the Arizona native.

Aside from the music, Ross explained that another common interest he shares with Bentley is their love for the outdoors. When he’s on the road, instead of hanging out on the bus and playing video games like many other artists admit to doing to pass the time, the “Single Again” singer chooses to find a way to connect with nature.

“I’m not as video gamey, I’m like, let’s go find a pond and go fishing…that’d be my main obsession is trying to get out and be in the outdoors. I think depending on where we are, it’s refreshing. We were down in Nashville, it’s a hundred plus degrees a month ago and we go up to Nebraska or somewhere and it’s 75 or 80 and it’s beautiful and it’s like, okay, I want to go to a pond and go fishing and enjoy the outdoors and I’m just a big outdoors person.”

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Seeing how much time Bentley dedicates to enjoying the outdoors through hiking, camping, biking, and more, Ross now aspires to find a better balance between his time performing and his time outside.

“I’m a little bit jealous. It seems like he’s got the outdoor world figured out. I think he’s the only other act that I’ve shaken hands with and been like, ‘okay, he has more cuts on his hands than I do’ in regards to just being outdoors and it’s easy to tell who likes to work on things and do things on their own. I think he’s just an all-rounded guy that’s got it figured out.”

Dierks Bentley isn’t the only artist that Josh Ross is learning from these days. Following recent runs on tours with acts like Jelly Roll and Nickleback, he’s also picked up a few other life lessons along the way.

“I feel like Jelly Roll is so new and watching how he takes a lot of life lessons and has turned that into the power of music and what that can do for people. I’ve really learned that from him. And then Chad and the Nickelback crew, for me, would just definitely be, there’s an almost 30-year career there. How do I do that? And yeah, just very much just patience. And to me, slow growth is just as good if not better than really quick growth and then trying to figure it out.”

With every lesson Ross learns, he continues building a career and a presence that further solidifies his place in the business. Most recently he shared his moments of growth through his debut album, Later Tonight. The 15-track project features stand-out songs like “Single Again,” “Hate How You Look” and “Leave Me Too.”

This fall Josh Ross will join Dylan Scott for six U.S. dates before traveling overseas for back-to-back headline shows at London’s Camden Assembly. Then in 2026, he’ll launch his 17-date Later Tonight Tour across Canada beginning February 6.