The best country singer!! Loves to sing about vacationing on the beach and getting away.
by Princess December 16, 2004
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Mr. Chesney is an adult-contemporary singer disguised as a country singer... a fact that most people miss because 1) he wears a cowboy hat (to hide his bald head) and 2) Nashville sucks. Oh, and for all you clueless girls who find him hot, truth be told he really looks like a middle-aged turtle on steriods.
Screw Chesney, buy Dwight Yoakam's new CD "Blame the Vain" when it comes out on June 14th. LONG LIVE YOAKAM!
by me April 26, 2005
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A mild-mannered, diminutive singer of moderate talent who somehow caught the proverbial Lucky Train and got a record deal; then somehow after years of exposure became perceived as actually talented and a against all odds became a "star" in Country music.

Mr. Chesney is known for his hard work and for releasing one forgettable song after another with his careful, monotone delivery. His vocal style is known for being devoid of passion or emotion. But he is most known in more recent years for his signature "lick" of dropping the last word of a lyrical line to "talk" it.

Many attempts to explain his success have come up short. But one reviewer came close by simply citing "The Emporer's New Clothes."
Kenny Chesney shows his lack of talent in the song "Another Beer In Mexico" or 80% of his other recordings.
by ThePointe March 18, 2008
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Peyton Manning's gay lover, they often have butt sex. General faggot.
(Peyton runs into room crying like a little girl)
Kenny Chesney: What's wrong hun?
Peyton: WAAAAAAH! That mean bully Tracy Porter ruined my game, and my line sucks waaaaaaaaaaaaaah!
Kenny: There there Peyton, I still love you.
Peyton: Sniff, can we still have butt sex?
Kenny: Sure
(Little does Peyton know, Kenny is cheating on him with the neighbors gerbil)
by pacman jones32 February 22, 2010
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A VERY HOTT AND SEXY COUNTRY SINGER and does NOT look like a turtle on steroids he sings great music and he is ver talented!!
Kennys tractor isnt the only thing thats sexy!
by Cassie Chesney August 21, 2005
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A popular country singer among trailer-trash women, who are on average more then double his weight. He's rumored to be gay and probably is.
Bertha and Betty-Joe-Bob love them some Kenny Chesney... and ranch flavored doritos.
by Brian the Definer November 16, 2006
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