Credit: Allister Ann

Since hitting it big with 2002’s No Shoes, No Shirt, No Problem, Kenny Chesney has become country music’s steadiest supplier of hommock-ready, fun-in-the-sun anthems. That’s helped him sell more than 30 million albums and rack up 25 No. 1 country hits, but it may not have made him very happy—at lest judging by the song “Rich and Miserable” from his 17th LP. It’s one of several tracks that find him wrestling with big, sometimes cheeseball questions about what a fulfilling life looks like: If we’re all going to die one day, why shouldn’t we cut loose now (“Trip Around the Sun”)? And in the echo chambers of social media and cable news, is there any room for real conversation (“Noise”)? Chesney has said he was on a mission to create songs that are “fun but not dumb,” and he mostly succeeds. The album’s best moments are the stadium-filling tunes about knocking back beers and longing for old times, like the Pink duet “Setting the World on Fire.” Yet his attempts at digging deeper make the lighter material feel earned—and they elevate his work above much of country’s escapist fare.

“Trip Around the Sun”

The cheery album opener, co-written with Lady Gaga collaborator Hillary Lindsey

“Setting the World on Fire”

An anthemic duet that shines thanks to a hair-raising hook from Pink