Out of context, Kenny Chesney seems like a strange addition to this picture of hip-hop stars Ja Rule and Ashanti. The two collaborated often in the early 2000s and maybe even (probably?) dated ...

Kenny Chesney — who is currently on tour with fellow country star Kelsea Ballerini — celebrated his 55th birthday with the "Heartfirst" songstress and friends on a private plane, sharing a ...

But the most memorable picture comes to us from Kenny Chesney's Instagram: "One fun, late night birthday plane ride after our State College, Pa. show with @KelseaBallerini. What a blast.

Released in the early 2000s, Chesney and Uncle Kracker watched as the hit song struck a chord with fans. Quickly climbing the charts, “When The Sun Goes Down” landed No. 1 on the US Billboard ...

Kenny Chesney is celebrating another trip around the sun. On Wednesday, March 26, the "When the Sun Goes Down" crooner celebrated his 57th birthday, commemorating the occasion with a peaceful ...

Kenny Chesney and Mac MacAnally started off their tribute with an acoustic cover of Buffett's "A Pirate Looks At Forty," both playing guitar on a smaller stage in front of the main stage.