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. 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.
Birthday: March 26, 1968
Top Songs: 'Summertime,' 'She Thinks My Tractor's Sexy,' 'You and Tequila'
Fun Fact: With the exception of 'The Tin Man,' every single Chesney released in the '00s reached the Top 10. That's 28 singles!