That’s quite an experience. Kenny Chesney shared a great story with Ashley Till during a special town hall on SiriusXM’s No Shoes Radio this week in celebration of his new book, Heart Life Music, which is set for release soon on November 4th. While he’s clearly had a long and successful career, Chesney recalled a time back when he first started and was selected to go on tour with George Jones and Tammy Wynette for their reunion tour in 1995. He of course grew up listening to Jones’ music, and when George’s wife Nancy offered to let him fly on their private plane, he jumped at the chance. It was the first time Chesney, a young man at the time from East Tennessee, had ever been on a private jet, and he sat there and talked to George about his life, his family and how he grew up. They hit it off, and Chesney says it was the beginning of a “really great friendship”: “Well, all of it. I mean, there’s a couple. When I first started, about a year after I went on the road, somehow, I was picked to go on the George Jones and Tammy Wynette reunion tour, and all of a sudden, there was this kid from East Tennessee that heard George Jones and his grandmother’s kitchen, and I was out on the road with them. One night, after a couple of weekends, George’s wife Nancy came up to me and she goes, ‘Would you like to fly home with us?’ and I’d never seen a private jet much less ridden in one, so all of a sudden, I’m on the plane with George and we’re talking about my life. I’m telling him about my family and how much we loved him, and I didn’t want to go overboard because I didn’t want to seem like that guy, but I mean, he really took it in and loved it and that was the beginning of a really great friendship.” I can’t even imagine not only that being his first time to ride on a private plane, but to do it with George Jones… it must’ve been incredible to just get to sit and talk to him like that. Chesney also told a great story about meeting Bruce Springsteen, and how he walked right up to his bus and knocked on the door. His manager gave him a heads up, and he thought it was a joke, but a few minuets later, Bruce came up on his motorcycle. He had watched their show from the front of house sound area, and of course, was an almost out of body experience for Kenny: “One night, I was in Holmdel, New Jersey. This was several years later, way after the ‘No Shoes’ album came out and we were rolling really hard and we were playing the amphitheater in Holmdel, New Jersey and I get a call from my tour promoter, Louis Messina, and he says, ‘Bruce Springsteen’s getting ready to knock on your bus door.’ And you’re not really, I went, ‘Okay,’ and the next thing you hear is, and I open the door and it’s really Bruce Springsteen, and he comes up on the bus and we chat a little bit and I had a couple of my guys. He came by himself on his motorcycle, and I had a couple of my crew guys walking him out. He literally, he didn’t watch from the side of the stage. He walked right through the audience and sat up at the front of house sound, at the front of house mixing board and watched the whole show, and then he came back to the bus and we sat and talked I bet for two hours and it was one, I talk about that moment in the book, and that started a really, really amazing friendship with Bruce and he didn’t have to do that, but I’m glad he did.” With both of those experiences happening pretty early in his career, it had to have been invaluable to have that type of support from two of the world’s most iconic musicians. Both Jones and Springsteen are absolute legends in their genre, who of course had a huge influence on Kenny and his music. It must’ve been even more special to have a personal relationship with them once he really started to get some momentum in his early country career, and I’m sure there are tons more stories like that in his book that I hope to get my hands on at some point. In addition to putting out the book, Chesney will return to the Las Vegas Sphere in 2026 for several more shows there. I Go Back 2026 Las Vegas Sphere Dates Friday, June 19 Saturday, June 20 Wednesday, June 24 Friday, June 26 Saturday, June 27The post Kenny Chesney Recalls First Time Ever Riding On Private Jet Was With George Jones: “Beginning Of A Really Great Friendship” first appeared on Whiskey Riff.