Kenny Chesney Surpasses Expectations

Kenny Chesney wins Entertainer of the Year at "The 42nd Annual CMA Awards," on Wednesday, Nov. 12, 2008, live from the Sommet Center in Nashville on the ABC Television Network. Photographer: John Russell / CMA 11/12/2008 Provided by Country Music Association

Nov. 14, 2008 — Kenny Chesney got choked up for just a second or two when he closed the Country Music Association Awards by winning Entertainer of the Year on Wednesday. He joined Garth Brooks as the only artist ever to claim the trophy four times, and he admitted backstage that it hit him harder than he had anticipated.

"It’s unbelievable really," he said. "It’s a lot more than I thought, winning the CMA Entertainer of the Year award for the fourth time in the last five years. It’s a lot more than this kid ever dreamed of. I didn’t know that my life was gonna be like this, you know. I was just happy when I got my first Top 5 record, and I was very, very happy just to get a tour bus and tour around the country with my buddies."

In fact, this week’s victory put Kenny in a nostalgic mood, taking him back in time to when he was still living in East Tennessee and trying to figure out his future.

"I remember bein’ in college and we were in a Laundromat doin’ our laundry," Kenny told reporters. "I was with a guy named David Farmer, who’s now my road manager. I was playin’ clubs. He goes, ‘What do you wanna do?’ And I said, ‘I think it’d be a lot of fun just to get a song on the radio and take all my buddies and go around the country just for one summer and play music and see the world.’ This comin’ summer will be my 16th summer, so I’ve been very blessed."

Indeed, Kenny is thinking strongly about next summer. He’s already seen a 3-D model of his 2009 stage, and he suggested the tour will kick off in April.