Kenny Chesney Paid Taylor Swift ‘Quite a Bit’ When a Joint Tour Fell Apart, Then Said ‘Gimme My Money Back’ After Her CMA Win

Taylor Swift and Kenny Chesney have long had a very sweet mutual admiration society. But when the “Take Her Home” country star appeared on The Tonight Show on Thursday night (Jan. 16), he revealed that the early stages of their friendship famously got off to a rocky start.

Chesney recalled the oft-repeated story about how when Swift was 17 she was booked to open a tour for him that was 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 now seems absurd, right?”

Chesney said he made the difficult call and told Swift he felt terrible about the bait-and-switch because he knew she was going to lose money from the scotched gig. “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.

Later, both singers were nominated for CMAs entertainer of the year. “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.’”

The question came after Fallon mentioned that Swift gave Chesney a shout-out in her TIME magazine Person of the Year essay in 2023, noting that she got kicked off his tour when she was 17, at a time when she thought the outing was “going to change my career… I was so excited.”

She confirmed then that the generous country star sent her a card and a check for her 18th birthday, “for more money that I’d ever seen in my life. I was able to pay my band bonuses. I was able to pay for my tour buses. I was able to fuel my dreams.” Chesney was one of the first to congratulate Swift her her Person of the Year honor, writing on Instagram at the time, “Taylor, I knew looking in your eyes that first time on stage with us, you had ‘it.’ It’s been awesome watching you shine!”

During the chat, Chesney also shared a funny pic from his summer tour with Megan Moroney, when the “Am I Okay?” singer surprised the headliner by going to his tour bus and put on one of his signature tank tops and whit cowboy hats before taking the stage dressed as him. “It just goes to show you that not only is Megan a great songwriter, she’s got a really good personality,” he said.

Chesney also talked 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 and longtime Coral Reefer Band member Mac McAnally. “That was a tough night. It really was,” Chesney said. “Jimmy taught a lot of us how to paint pictures with words. For that reason I’ve always looked up to Jimmy Buffett.”

The singer who just announced an upcoming residency gig at the immersive Sphere in Las Vegas, told Fallon that he signed up for the run despite never seeing a show at the eye-popping, state-of-the-art venue. But when he went to check it out, he said, “it’s like we’re all just… the band, the audience, is all in a completely different state of consciousness. And I looked at my crew and my team and I went, ‘There’s no way we’re not not doing this!’”

The only downside he said, is that because all the mind-bending visuals are shot in super hi-def 36K, all the visuals and footage Chesney has used over the years during his stadium shows were not gonna cut it. “Which is good, because it just makes it really new and fresh,” he promised of the show that he’s already in rehearsals for.

Chesney’s Sphere residency will kick off on May 24.

Watch Chesney on The Tonight Show below..