Kenny Chesney Drops in for a Low-Key Performance at Key West Bar [Watch]Kenny Chesney Drops in for a Low-Key Performance at Key West Bar [Watch]Surprise! Chesney popped up in a Florida beach saloon for an impromptu performance of "You and Tequila."Carena LiptakCarena Liptak
30 Years Ago: Kenny Chesney Signs His First Record Deal30 Years Ago: Kenny Chesney Signs His First Record DealOn June 30, 1993, Chesney signed his first record deal, with the newly opened country division of Capricorn Records.Annie ZaleskiAnnie Zaleski
Top 10 Country Songs About SummertimeTop 10 Country Songs About Summertime"Summertime, and the livin' is easy" -- so goes the old American standard.The Boot StaffThe Boot Staff
20 Years Ago: Kenny Chesney Headlines His First Stadium Concert20 Years Ago: Kenny Chesney Headlines His First Stadium ConcertOn June 7, 2003, Chesney set a career milestone: He headlined his first stadium concert.Annie ZaleskiAnnie Zaleski
15 Songs You Didn’t Know Phil Vassar Wrote15 Songs You Didn’t Know Phil Vassar WroteYou know "Carlene" and "Just Another Day in Paradise," but did you know Phil Vassar also wrote these country hits for other artists?Lorie LiebigLorie Liebig
Old Dominion Prank Kenny Chesney by Crashing an ‘I Go Back’ Tour StopOld Dominion Prank Kenny Chesney by Crashing an ‘I Go Back’ Tour StopChesney got the surprise of his life when his longtime buddies walked out onstage.Carena LiptakCarena Liptak
Would Kenny Chesney Ever Play the Super Bowl Halftime Show? He’s Not So SureWould Kenny Chesney Ever Play the Super Bowl Halftime Show? He’s Not So SureThat doesn't mean he wouldn't say yes.Evan PaulEvan Paul
Kenny Chesney Brought His Mom Onstage to Sing With Him in South Carolina [Watch]Kenny Chesney Brought His Mom Onstage to Sing With Him in South Carolina [Watch]Kenny Chesney is arguably one of the best country music artists of his time, but at the end of the day, he's still all about his mama.Evan PaulEvan Paul
Who Is Country's Best Living Performer?Who Is Country's Best Living Performer?Carrie Underwood? Kenny Chesney? Garth Brooks? George Strait? Which artist puts on the best concert?Billy DukesBilly Dukes
Kenny Chesney Celebrated His Birthday on a Late-Night Plane Ride With Kelsea Ballerini and Friends [Picture]Kenny Chesney Celebrated His Birthday on a Late-Night Plane Ride With Kelsea Ballerini and Friends [Picture]And while he works hard, Chesney plays hard, too.Evan PaulEvan Paul