Chesney once paid Taylor Swift not to tour with him. After booking her as a support, he realized he’d scheduled a minor to open shows sponsored by Corona Light beer. “I had to call her and tell her she couldn’t be on the tour,” he says. He also gave her a hefty check by way of apology. Not long afterward, Swift ended Chesney’s four-year run as the Country Music Association’s entertainer of the year, keeping him from breaking a record he still shares with Garth Brooks. “I went up to her backstage, gave her a hug and told her I wanted my money back.