Kenny Chesney is a five-time Academy of Country Music and Country Music Association Entertainer of the Year award winner, as well as a Grammy Award-winning country music singer and songwriter. He has released over 20 albums since his debut in 1993, and has had 30 singles reach the top of the Billboard Hot Country Songs chart. His most popular songs include 'She Thinks My Tractor's Sexy, ' 'No Shoes, No Shirt, No Problems, ' and 'When the Sun Goes Down.'