Kenny Chesney has recorded 15 albums, 14 of which have been certified gold or higher by the RIAA. He has also produced more than 30 Top Ten singles on the U.S. Billboard Hot Country Songs charts, 22 of which climbed to the top of the charts.

The Country Music Association honored Chesney with the Entertainer of the Year award in 2004, 2006, 2007, and 2008. Other notable awards include the Academy of Country Music's 1997 New Male Vocalist of the Year, 2002 Top Male Vocalist of the Year, and the Triple Crown Award in 2005. He was awarded his fourth consecutive Entertainer of the Year award from the Academy of Country Music on May 18, 2008.