He won 2 awards at the 2002 CMT Flameworthy Awards. One for video of the year for "Young" and one for male artist of the year!
| 2003 ACM's, Kenny won the Top Male Vocalist award and Single of The year for "The Good Stuff"! |  |
CMT Flameworthy awards April 21, 2004, he won Hottest Video of the year for "No Shoes, No Shirt, No Problems" and also won Male Video of The Year for "There Goes My Life".
| CMA awards November 9th, 2004. Kenny won Album on the Year for When The Sun Goes Down and the top award, Entertainer of the Year! |  |
AMA awards, November 14, 2004. Kenny won the fan voted award for Artist of the Year! This was for all music types, not just country.
ACM awards, May 2005. Kenny won the top award, Entertainer of the year! This put him in with the elite few to ever win the ACM Triple Crown, a singer who has won New Male Vocalist, Top Male Vocalist, and Entertainer of the Year.
