Now, as Chesney heads into the Country Music Hall of Fame’s Class of 2025, Vassar is speaking out about why his longtime pal deserves the honor.
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Vassar, 63, explained that the “She Thinks My Tractor’s Sexy” hitmaker is the kind of person who shows up first and leaves last. “He’s always been that guy,” he said. “We always had so much fun when I was on the road with him.”
Still, it wasn’t just the grind that impressed him. Vassar shared that Chesney also offered career guidance when he was getting started—everything from navigating record labels to decoding contracts. “He’s a really smart guy and he doesn’t let things get out of whack,” he added. “I got a lot of good advice from him.”
“This is the guy who has made country music, made the live show, made his fans his life’s mission,” @DierksBentley says of @kennychesney, ahead of Chesney's @countrymusichof induction. t.co/eYJjv5AIcQ pic.twitter.com/xOIkN8QLwG
— Everything Nash (@EveryNashThing) August 4, 2025? SIGN UP for our The Voice newsletter to get access to exclusive news, interviews, insider info, sneak peeks & more ?
Pure joy on stage this summer with @_megmoroney. #SunGoesDownTour pic.twitter.com/XVXURO6iBA
— Kenny Chesney (@kennychesney) June 19, 2024This fall’s Class of 2025 pairs the East Tennessee native with June Carter Cash and Tony Brown. Chesney is this year’s Modern Era Artist inductee, celebrated for more than 30 years of hits, from “How Forever Feels” and “The Good Stuff” to anthems like “No Shoes, No Shirt, No Problems.” He’s also one of country’s most consistent touring draws, headlining stadiums for over two decades.
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