Kenny Chesney recently shared a story about how his friendship with Taylor Swift had a rough start. When Swift was 17, she was set to open for Chesney on tour, but the beer company sponsoring the event wouldn’t allow a minor on the tour. Chesney had to personally call Swift and break the bad news, but he felt terrible about it. To make it up to her, he sent her a generous check for her 18th birthday, which helped her pay her band and tour expenses.
“They came to us right before the tour started and said, ‘We can’t have a minor on the tour,’” Chesney recalled. “Which made sense. But I had to call Taylor personally and tell her she couldn’t go on tour with me, which now seems absurd, right? “I gave her a specific amount of money… it was quite a bit of money, because I wanted to make it up to her,” said Chesney.
Years later, when Swift won the CMA Entertainer of the Year award in 2009, Chesney congratulated her backstage and jokingly asked for his money back. Swift later mentioned Chesney’s kindness in her 2023 TIME Person of the Year essay, saying his gift helped fuel her dreams. Chesney responded on Instagram, praising her talent and success.
“Well, she won,” explained Chesney, a four-time winner of the award, of Swift’s first of two CMA top honors in 2009. “So, backstage, I went up to her and gave her a big hug. I said ‘congratulations, but gimme my money back.’”
During his appearance on The Tonight Show, Chesney also talked about Megan Moroney’s playful tribute to him on tour, his close friendship with the late Jimmy Buffett, and his upcoming Las Vegas residency at the Sphere. He described the venue as an entirely new experience and is excited about the high-tech visuals that will make his show feel fresh and unique.
