Kenny Chesney began his career as a traditionalist, but soon created his own unique brand. He fused rock with the beach and raw, honest and often nostalgic lyrics of love and life. There wasn’t a more successful artist in the 2000s. Chesney is a four-time Entertainer of the Year Award winner at both the CMAs and ACMs. The Luttrell, Tenn. native made his mark with his third album, ‘Me and You,’ in 1996, but “She Thinks My Tractor’s Sexy” from 1999 really made him a star. Chesney built his career on laid-back, good-time hits like “No Shoes, No Shirt, No Problems,” “When the Sun Goes Down” and “Out Last Night,” but he’s also cut harder-hitting songs like “There Goes My Life” and “The Boys of Fall.” In recent years he has focused on the more serious side of his music with songs like “You and Tequila” and “When I See This Bar.” He is one of the most perennially successful live performers in country, playing to a vast audience that is collectively known as the No Shoes Nation. In addition to his music, Chesney is known for his dedicated workout regimen and for being something of a ladies man. In May 2005, he married actress Renee Zellweger, but their union was annulled four months later. Since then, Chesney has almost always remained mum about his private life.