Kenny also had the chance to chat about a few other country music superstars.
“I was really proud and really happy that he won,” Chesney said of Brad Paisley’s Entertainer of the Year win. “To stand in that spot, it isn’t free, it’s not. People don’t give that to you. You’ve to go out and put yourself in a position to win in it. Then after that, you’ve gotta go even further and win it. I saw him at the party after and gave him a big hug and told him how proud I was for him and happy that he’s gonna do down in history as being one of the guys that got to stand in that spot.”
Chesney also gave Paisley some words of wisdom that he once received from the King of country music.
“Like [George] Strait told me, the first year that I won Entertainer of the Year I also won Album of the Year, and he sent me this great letter and he said, ‘winning album of the year says a lot, winning entertainer says it all.’ I told Brad that too.”
Chesney also reveals that he’s close with another superstar who holds an Entertainer of the Year title.
“Taylor [Swift] and I are very good friends and I’ve known her for a while,” he said. “The first time she won Entertainer of the Year, the year before she was gonna go out on the road with us. That was the first year that my tour was gonna be sponsored by Corona and so there was some sort of legal, contractual thing where people weren’t comfortable with having an alcohol sponsored show and having a 17 or 18 year old on the show. So, I had to call Taylor and tell her that she couldn’t do that tour. And I gave her, as an ‘I’m sorry’ present, I gave her a lot of money. So fast forward [to] the next year and she’s nominated for Entertainer of the Year, as am I, and she wins. So, I’m backstage and I come up behind her, she was hugging her band, and I come up behind her and gave her a hug and I said, ‘I want my money back.’
“So I haven’t gotten it back yet, but maybe I will one day, who knows,” he said with a laugh.