Kenny Chesney Is Waiting for Taylor Swift’s ‘Payback’

From 2004 to 2008, Kenny Chesney was crowned Entertainer of the Year a total of eight times: four by the CMA ('04, '06, '07, '08) and four consecutive times by the ACM ('05 - '08). Not once, over the course of those years, did the superstar take for granted the enormity of those honors.

"To stand in that spot, it isn't free ... it's not," the 'Somewhere With You' singer tells CMT Country Countdown USA. "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."

In 2009, Taylor Swift was crowned CMA Entertainer of the Year, usurping Kenny's three-year reign. "Taylor and I are very good friends and I've known her for a while," he shares. "The first time she won Entertainer of the Year, the year before she was going out on the road with us. That was the first year that my tour was gonna be sponsored by Corona, so there was some sort of legal 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."

Hoping to make up for any disappointment that then-teenaged Taylor might have felt, Kenny figured he'd give her a little something. "I gave her, as an 'I'm sorry' present, I gave her a lot of money," he continues. "So fast forward [to] the next year [2009] 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!' [laughs]"

Three years later, Kenny says -- tongue planted firmly in cheek -- that he's still waiting. "So I haven't gotten it back yet, but maybe I will one day ... who knows," he says with a laugh.

Last November, Brad Paisley was crowned the 2010 CMA Entertainer of the Year. "I was really proud and really happy that [Brad] won," Kenny remembers. "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 go down in history as being one of the guys that got to stand in that spot."

Kenny was so moved, in fact, that he passed on the words of wisdom George Strait shared with East Tennesse native. "Like [George] Strait told me, the first year that I won Entertainer of the Year, I also won Album of the Year," Kenny continues. "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."

Kenny's current single, 'Somewhere With You' is currently atop the charts for the second consecutive week. He kicks off his Goin' Coastal tour March 17 in West Palm Beach, Fla. Get details here.

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