Taylor Swift and Kenny Chesney have had a very sweet mutual admiration society for a long time. But when the “Take Her Home” country star appeared on Tonight’s show On Thursday evening (January 16), he revealed that the early stages of their friendship got off to a rocky start.
Chesney recalled the oft-repeated story that, when Swift was 17, she was booked to open for him on a tour sponsored by a beer company. “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 seems absurd now, right?
Chesney said he made the difficult decision and told Swift he felt bad about the bait and switch because he knew she was going to lose money from the Scottish concert . “I gave him a specific amount of money…it was a big amount of money, because I wanted to make it up to him,” Chesney said.
Later, both singers were nominated for the CMA Entertainer of the Year Award. “Well, she won,” said Chesney, a four-time winner of the award, the first of two major honors given to Swift in 2009. “So, backstage, I walked up to her and gave her a big hug. I said “congratulations, but give me my money back.”
The question came after Fallon mentioned that Swift had yelled at Chesney in her TIME in a 2023 Person of the Year magazine article, noting that she began touring at the age of 17, at a time when she thought the release “was going to change my career…I was so excited” .
She then confirmed that the generous country star sent her a card and check for her 18th birthday, “for more money than I’ve ever seen in my life.” I was able to pay my group’s premiums. I was able to pay for my tourist buses. I was able to fuel my dreams. Chesney was one of the first to congratulate Swift on her Person of the Year title, writing on Instagram at the time: “Taylor, I knew when I looked into your eyes the first time on stage with us, you had it. It was great to see you shine! »
During the chat, Chesney also shared a fun photo from his summer tour with Megan Moroney, when the message “Am I okay?” » The singer surprised the headliner by heading onto his tour bus and donning one of his signature tank tops and white cowboy hats before taking the stage dressed as him. “It shows that Megan is not only a great songwriter, but she has a really good personality,” he said.
Chesney also spoke about his long friendship with Jimmy Buffett, his tribute to the “Cheeseburger in Paradise” singer at last year’s Rock and Roll Hall of Fame induction ceremony alongside James Taylor and Mac McAnally, a longtime member of the Coral Reefer Band. “It was a difficult evening. It really was,” Chesney said. “Jimmy taught many of us how to paint pictures with words. This is why I have always admired Jimmy Buffett.
The singer, who just announced an upcoming residency concert at the immersive Sphere in Las Vegas, told Fallon that he signed up for the race even though he had never seen a show at the stunning, state-of-the-art venue . But when he went to see it, he said, “It’s like we’re all just… the band, the audience, are all in a completely different state of consciousness.” And I looked at my crew and my team and I was like, “There’s no way we’re not going to do this!” »
The only downside, he said, is that because all of the stunning visuals are shot in 36K super high definition, all of the visuals and footage Chesney has used over the years in his stadium shows were not going to work. not enough. “Which is good, because it makes it really new and fresh,” he promised of the show he’s already in rehearsals for.
Chesney’s Sphere residency will begin on May 24.
Watch Chesney on Tonight’s show below..
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