Kenny Chesney is The Most Entertaining Cowboy In History

By Stuart Heritage on Thursday, November 13, 2008 at 5:00pm3 Comments


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You know what we like in an entertainer? The wild hope that wearing a big hat will cover for an overwhelming lack of charisma.

And we’re not the only ones, because Kenny Chesney – a man with a big hat and hardly any charisma – has just won the CMA Entertainer Of The Year award for the fourth time in five years, making him officially the most entertaining country singer ever born. Except for Garth Brooks. He’s equally entertaining.

This must count as one of Kenny Chesney’s proudest moments. Now he can look back on all the other country singers of the past and know he’s more entertaining than them. He’s more entertaining than Billy Shooter, Old Jeb Clovercleb, Whistlin’ Jimmy McFormaldahide, Redeyes O’Murderer and even, in a controversial twist, Barefoot Bobby And The Pregnant Mistakes. Congratulations, Kenny Chesney. You earnt this.

Being an entertaining country singer is a lot like being a successful plate-spinner – you have to try and make references to farming equipment at the same time as keeping up your quota of lengthy pun-filled song-titles, without forgetting about blind patriotism that regularly veers into racism or the fact that your personal life has to include some form of mild tragedy.

It sounds exhausting, which is why we should all be congratulating Kenny Chesney for being named the most entertaining country performer at last night’s Country Music Awards – something he seems to have been given for being the only country performer who hasn’t punched any of his fans or shot a stranger in the face recently.

More than that, in fact, Kenny Chesney has now won the CMA Entertainer Of The Year award four times in five years, more than anyone else except for Garth Brooks, whose record he has tied. And, to think, all he had to do to get there was marry a skinny actress briefly and constantly deny that he’s gay.

Obviously what makes Kenny Chesney so entertaining is his noble humility, which he displayed last night after winning his award. AP reports:

“Winning entertainer of year for the fourth time in five years is more than this kid ever dreamed of,” Chesney said backstage. While Chesney knows his reign will eventually end, he said, “I’m not going to lay down. I love the heart, commitment and sacrifice it takes to do this.” And to his competitors, he issued a challenge: “Come and get me.”

We think Kenny Chesney is being too modest. He’s never going to stop being the most entertaining country singer on Earth because, like he said, he understands the sacrifice that winning it takes.

For instance, all Kenny Chesney really wants to do is work 20-hour shifts down a mineshaft every day for the rest of his life but, oh no, there’s always someone on his back telling him to earn millions of dollars by endlessly recycling his one already-generic idea into another best-selling album. Now that’s sacrifice.

But, still, this must be an important award for Kenny Chesney because it’s the first award he’s won for ages where he didn’t act like a turd about it afterwards.

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3 Comments »

  • Ellen Grant says:

    What a jealous humorless jerk you are. Get a life! Kenny did and a darn good one too! I love his music, his heart, his enthusiasm and genuine love of his fans. I’ve met him but I bet you haven’t. Don’t get me wrong, I really enjoyed 2/3 of the singers on last night and listen to them regularly but having gone to quite a few concerts…..Kenny’s is hands down the best time and the only one I will spend all my money going to in the future! CONGRATS KENNY!!!!

  • Gilbert Wham says:

    arefoot Bobby And The Pregnant Mistakes is a fucking amazing band name. Up there with Kinky Friedman and the Texas Jewboys fer sure.

  • Gail says:

    I heard a Country radio DJ say that Kenny’s record label fights hard and pays alot to get Kenny that trophy every year. I figure Kenny must not have been their pick for EOTY! He throws a drunkfest….no wonder he sells tickets. It’s not about the music with him…it’s how he can keep everybody drunk. Been to 2 of his concerts and that was enough for me. Nobody knew or cared who was on stage!

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