When the Sun Goes Down represents not only Kenny Chesney’s commercial peak (it’s tough to think of many bigger country blockbusters from the time) but also one of his most important points of definition. Here Chesney inhabits the pop-friendly approach he had embraced on Everywhere We Go more fully and organically than ever before. Consequently, he’s more completely himself here than ever, showing the multiple sides of his musical personality and coming off consistently natural-sounding in the bargain. The country-pop-rock mergers feel more seamless than they did on his previous albums, and along with the broad appeal of the songs, Chesney is revealed to be quite the storyteller. The songs that Chesney wrote or co-wrote himself capture vivid moments that underline personal connections, whether we get a snapshot of him singing along to John Mellencamp on the sweeping hit “I Go Back” or a detail-rich account of his college days on the rock-infused “Keg In the Closet.” But the outside material Chesney chose for the album is just as loaded with potent imagery. The storytelling vibe even extends to the spoken-narrative verses that burst out of the sung refrains on “When I Think About Leaving.” Good-time trop-rocking tunes like the easy-bumping title track (a duet with Uncle Kracker) and “Outta Here” continue the Jimmy Buffett-gone-country thread that helped make Chesney’s previous album, No Shoes, No Shirt, No Problems, such a smash. The latter tune doubles down on the intention, throwing steel drums and a Key West shout-out into the mix. Ultimately, When the Sun Goes Down is the sound of a man feeling his oats and meeting his moment of maximum superstardom with a measured approach, making sure he’s fully invested in every bit of the record. Chesney still had more changes ahead of him, but this album marks his arrival at a place he’d been slowly moving toward for years, even if he didn’t know it until he got there.