Kenny Chesney was born March 26, 1968, in Knoxville, Tenn., and raised in nearby Luttrell. His Greatest Hits (2001) sold more than 3 million copies. No Shoes, No Shirt, No Problems (2002) catapulted him into the big leagues and played up his fascination with the islands. At the end of 2003, he rested atop the Billboard country singles chart with the hit "There Goes My Life." In 2004, that album When the Sun Goes Down won a CMA Award, and Chesney captured the CMA entertainer of the year trophy. He offered Be As You Are: Songs From an Old Blue Chair, an introspective singer-songwriter album inspired by his love for the islands, in early 2005.

Chesney surprise marriage to actress Renée Zellweger was annulled later that year. Chesney released the album The Road and the Radio in November 2005. He released Live: Live Those Songs Again in 2006 and celebrated career sales of 25 million albums. Chesney also capped the year by winning his second CMA entertainer trophys.