Kenny Chesney Recalls Telling Taylor Swift She Couldn’t Tour With Him Early In Her Career

During a recent appearance on The Tonight Show Starring Jimmy Fallon, Kenny Chesney recounted a story about his planned tour with Taylor Swift in her early days that never materialized. The 56-year-old country star said that Swift was set to open for him back when she was a rising 17-year-old country singer, but because the tour was sponsored by a beer company, Swift couldn’t take part because she was a minor. “I had to call Taylor personally and tell her she couldn’t go on tour with me, which now seems absurd, right?” Chesney recalled, saying he felt bad because “she was going to lose some money.” So Chesney personally wrote Swift a check to make up for it. Later that year, both singers were nominated for CMA Entertainer of the Year. “Well, she won,” Chesney said. “So backstage I went up to her and gave her a big hug. I said, ‘Congratulations but give me my money back.’” (People)