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10.
This punk is a balding, rather fugly, cunt tree singer who is, for some unknown reason, loved by millions of females across America, mostly in The South and parts of the lower Midwest (mostly Kentucky, Missouri, and southern Illinois). He has a horrid accent, can't even sing, and is pretty dumb.
Hi! Ah'm Keen-ny Chesn-ney and ah love the Confederate flahg, greetz, 'mater samitches (fried green tomatoes/sandwiches), and makin' kuntree muuzic. A-hyuck!
by damyankee May 25, 2005
115 175
 
1.
The best country singer!! Loves to sing about vacationing on the beach and getting away.
Kenny Chesney is fucking HOT!!!
by Princess December 15, 2004
258 212
 
2.
When a black guy gives a white guy a dirty sanchez
I walked into the bathroom and there was Tyrone giving Mike a Kenny Chesney in the shower.
by rainmaker32 June 23, 2009
92 66
 
3.
Proof that God loves us and wants us all to be happy.
Kenny Chesney has the BEST fan club EVER!
by April Chesney July 26, 2005
203 184
 
4.
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
168 175
 
5.
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 TheRapist45 February 21, 2010
79 86
 
6.
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 17, 2008
94 102
 
7.
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 25, 2005
162 180