Kenny Chesney and Phil Vassar go way back. Long before the 57-year-old Hall of Fame inductee was selling out stadiums and headlining the Sphere in Las Vegas, the two were crossing paths in writing rooms and on the road. Vassar even toured alongside Chesney in the early 2000s, cementing a friendship that’s lasted for decades.
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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In a Taste of Country Nights interview published Friday, August 15, the “Six-Pack Summer” singer didn’t hesitate when asked why Chesney belongs in the Hall: “The thing I’ve always admired about Kenny is his work ethic.”
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.”
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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.”
Vassar isn’t the only one singing Chesney’s praises. In a separate Taste of Country Nights interview published July 30, Dierks Bentley—who first toured with Chesney as an opener on the 2004 Guitars, Tiki Bars and a Whole Lotta Love tour—called him “such a great mentor.”
“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.https://t.co/eYJjv5AIcQ pic.twitter.com/xOIkN8QLwG
— Everything Nash (@EveryNashThing) August 4, 2025
“I love Kenny to death. I’m so proud of him for being in the Hall of Fame,” Bentley said, adding, “I learned so much about how to treat your band, how to treat your crew and how to treat your fans.”
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But praise didn’t stop with country vets—newer stars showed love, too. When Chesney’s induction was announced in April, rising country artist Megan Moroney—who broke out with “Tennessee Orange,” won CMA New Artist of the Year in 2024 and opened on Chesney’s 2024 Sun Goes Down tour—replied to his Instagram announcement with one word: “Deserved!!!!”
Pure joy on stage this summer with @_megmoroney. #SunGoesDownTour pic.twitter.com/XVXURO6iBA
— Kenny Chesney (@kennychesney) June 19, 2024
This 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.