The CMA Awards aren’t until Wednesday, but Kenny Chesney is already ready to knock fans’ cowboy boots off.

As preparation for his upcoming performance, the singer played a impromptu gig with legendary reggae band The Wailers at Tootsie Orchid Lounge in Nashville Monday night.

Word of the “commando show” had leaked to fans, who flooded the club to watch the award-winning singer run through nearly four hours of his own hits and reggae favorites that The Wailers helped popularize with Bob Marley. At one point, Chesney’s friend Kid Rock even joined in for a few songs.

Chesney’s biggest problem now may be trying to match Monday night’s show when he’s at the CMA Awards.

“We could hear %26#91;fans%26#93; making their way down the street on our bus after, and it was awesome,” Chesney said. “You know, hardcore country fans singing ‘One Love.’ Now that’s what I call making music universal.”

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Kenny Chesney is no stranger to stadiums - his Poets and Pirates tour has been packing sports arenas all summer long. But on his way to his New Orleans concert this Thursday, he hit the football field for real.

For the second year in a row, the country superstar lived out his gridiron fantasies by practicing with the New Orleans Saints in Jackson, Miss., according to the Associated Press.

Donning a white Saints game jersey with his name sewn on the back, Chesney, who is pals with the team’s coach, Sean Payton, ran plays with the team and caught a long pass from quarterback Drew Brees.

At the practice, which was open to the public, Payton told players they would get Sunday off if Chesney - who was a receiver on his Tennessee high school football team - caught a punt in two tries.

“On the first one, I totally blew it,” Chesney told the AP. “On the second one, not only were they offside, but they interfered with me.”

Luckily for the players, Chesney got a third try at redemption. As the ball landed in his hands, he juggled it - but refused to let it hit the ground.

Jubilant players whooped it up, including Reggie Bush - Kim Kardashian’s boyfriend - who winged a water bottle across the field in celebration.

“Reggie told me I better not drop the third one because he didn’t want to practice,” said Chesney.

Payton declared Chesney “part of our team” - an honor the sports loving singer embraced.

“I quit growing too young to ever think about getting to have a shot at playing in college,” said Chesney, “so this is about as much fun I can have.”

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• See how the country superstar made headlines on multiple PEOPLE covers.

Kenny Chesney is knocking down a tabloid report that he’s engaged.

“Kenny Chesney is not getting married. He’s not engaged. He’s not planning on being engaged any time in the near future,” his rep tells PEOPLE. “In fact, he was surprised by the news and isn’t sure how or why anyone would’ve gotten that idea. As he recently told PEOPLE, ‘I enjoy being a bachelor. I enjoy everything that comes along with it.’”

Chesney, 40, recently won the coveted entertainer of the year award at the Academy of Country Music Awards in Las Vegas.

Kenny Chesney has blogged about why he criticized the Academy of Country Music’s new method for choosing entertainer of the year by using fan votes.

“To me, Entertainer of the Year is about the work that goes into it. I don’t ever want you worrying about the work; I want you living the songs, being in the moment of the music,” the star tells fans on his MySpace page.

“That was my point. Let the people who do the work, judge the work part of it … let the fans love what we do for that,” he adds.

After winning the ACM award on Sunday night in Las Vegas, Chesney told reporters backstage that the organization had turned the category

“into a sweepstakes to see who can push people’s buttons the hardest on the Internet.”

This was the singer’s fourth consecutive win in that category, tying Garth Brooks for the honor.

Chesney also blamed the media for taking his comments out of context. “Sure, to make me sound ungrateful is a sexy way to spin this to drive viewers. It’s controversy, and that sells,” he writes.

“So please know I love you. I believe in you and the way you believe in this music, these nights we get to share, the way it call %26#91;sic%26#93; comes together when we’re together. There is nothing like the feeling of being out there with you guys and I live my whole life just for those moments. Thank you for that, because in the end, that is what matters the most to me.”

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Exclusive! Backstage Photos at the ACM Awards
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Kenny Chesney may “enjoy being a bachelor,” but the country music star tells PEOPLE he’ll give his next marriage “150 percent.”

“I thought I was ready once before, but I wasn’t,” Chesney, 40, said of his 4-month marriage to Renée Zellweger in 2005. “If I get married again, I’m going to give it 150 percent.”

The pair have remained close friends - Chesney even tells PEOPLE’s Country Special that she is “the sweetest soul I’ve ever met” - but he admits it was hard to cope with the split.

“There was nothing that made me happy,” he said. “You can’t fall in love as hard and fast as we did and not have some residual effects.”

Chesney, who was named entertainer of the year at Sunday’s Academy of Country Music Awards, added that he looks at it “as a life lesson.” Not to mention: “This is the happiest I’ve been in a long time.”

For more on Chesney, pick up the June issue of PEOPLE’s Country Special, on newsstands now

What happens in Vegas usually stays in Vegas. But this time Kenny Chesney might want to ignore that rule and tell all his friends about his night in Sin City. The singer won the coveted entertainer of the year award at the 43rd Annual Academy of Country Music Awards in Las Vegas on Sunday 
night.

“This one is really extra special because long before I had a hit
 record, the fans always came to the shows. And I want to thank you guys for voting and for being there for me,” said Chesney when accepting his award, which fans voted on for the first time. This is the singer’s fourth consecutive win in that category, tying Garth Brooks for the honor.

Taylor Swift, 18, who nabbed two major prizes at last month’s CMT Awards, dedicated her top new female vocalist award to her mom saying, “Mom, thank you so much. I love you. This is for you!”



Carrie Underwood, 25, took home the trophy for top female vocalist for the second consecutive year, and Brad Paisley, 35, won the same prize in the male category.

Other major winners of the night included Miranda Lambert’s “Crazy Ex-Girlfriend” for album of the year, Sugarland’s “Stay” for song of the year and Lady Antebellum for best new duo/vocal group. (Check out their People.com video diary here.)

The Performances

Underwood opened the ceremony with her performance of an appropriate Vegas song: “Last Name.” Later in the show, she joined Paisley onstage to pay tribute to the late country legend Eddy Arnold by singing “Make the World Go Away.”

Miranda Lambert heated things up with “Gun Powder and Lead.” Then, Swift cooled the stage back down with her dripping wet performance of “Should’ve Said No,” during which she danced in water pouring from the ceiling.

After performing solo, Chesney and George Strait, who was celebrating his 56th birthday, teamed up to sing their nominated duet “Shiftwork” for the first time live.


Surrounded by fans, dad-to-be Keith Urban, who says he’s “very excited” about fatherhood, performed “Tu Compania” along with new artist nominee Sarah Buxton as Urban’s wife Nicole Kidman watched on.

After LeAnn Rimes, Montgomery Gentry closed the show,
 which was hosted by Reba McEntire for the tenth time.


MORE ON THE AWARDS
Exclusive! Backstage at the ACM Awards
Vegas Goes Country! Photo Special
Caught in the Act: ACM Awards Edition!