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Chesney Goes Topless with Playboy Chick

4/6/2009 10:30 AM PDT BY TMZ STAFF

He may not have a lot of hair, but Kenny Chesney's sure got game.

Kenny Chesney
After losing at the ACMs, the country star scored with two blonde hotties at the Playboy Club last night in Las Vegas.

They think his bald head's sexy!

42 COMMENTS

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31.

ohnancie    

You are right on the money about him being BUTT UGLY>
He definitely never be GEORGE STRAIT.
I am glad that someone beat him out of the Entertainer of the Year award!

2025 days ago
32.

Mm    

When will he grow up?
There was somebody sitting next to him (probably his girlfriend called Amy), but the camera did not show her at all.

2025 days ago
33.

Deb    

That is his girlfriend Amy in the first picture, Amy was setting next to him at the awards show they make a great couple. Kenny's a good guy he should have won Entertainer of the Year, Carrie does not deserve this award.

As far as Kenny being bald hell he's a very handsome man with or without hair.

2025 days ago
34.

Steph    

Deb....why doesn't Carrie deserve to win? She works as hard as any in the business and is every ounce as talented! All who were considered for the award deserved to win it! Congrats to Carrie!!

2024 days ago
35.

shujinko    

He is freakin' creepy. Like a middle-aged pervert...who can't pull off a bald head. *Runs away*

2024 days ago
36.

goldieok    

keith urban got it over chesney ---- nicole & i have great taste in men LOL

2024 days ago
37.

Gloria    

I think he is hot inside and out and that he thought while im in vegas let me have some fun, Besides who wouldnt you dont go to vegas to see idk star treck! I think that might be his g/f in the 1st pic and shes all the reason he didnt win shes a bad luck gold digger.

2024 days ago
38.

Cayse    

I was there. I touched is bald head and it was creepy. He felt like Princess Diana at the bar and was doing the whole Renne fraud thing with beautiful girls except by using his name as a pass.

I'm from Oklahoma and never disliked him until he opened his mouth. Way too big of an ego for being an awful singer.

2024 days ago
39.

get out of the closet    

chesney is uber gay...

so is ryan secrest, ricky martin, anderson cooper

chesney was just checking her hair out to see if it was as soft as the escorts hair he hired the night before from all male escorts, los vegas!

2024 days ago
40.

Deb    

angela, Nope not Carrie the first picture is Amy Colley Kenny's girlfriend the next is a playboy bunny.

2022 days ago
41.

it's just me    

Who says he is trying to be George Strait...??? Anybody that has to compare Kenny with other entertainers are only jealous of the talent that Kenny does have! Kenny is friends with all of them. If you don't like Kenny..why take the time to read about him. I can't stand a lot of celebrities and I don't waste my time reading about them...only LOSERS do that!! Usually the ones making the bad comments are the jealous husbands or boyfriends to the ladies that love Kenny. So honestly I'm not bothered by the bad comments..it just tells me you've got some personal issues of your own.....you need help. So good luck to ya...don't stress over Kenny. Oh and the people admitting to be gay saying they know Kenny is....you only WISH you could have him...ha ha!! Sorry boys....!!

2022 days ago
42.

Mistywright    

I think that he is sexy with or without his hat I just want him to find himself a woman that loves him for his smalltown heart open the door for a woman side that he has instead of his money and things he has materially......yeah this is nice but the love means nothing to money as long as the two hearts fall in love all the other will fall into place. I love you Kenny Baby girls eat your heart out with the glasses, cowboy hat, backwards baseball cap, or nothing at all this man can sing my soul on fire forever and ever amen!

1448 days ago
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