05/20/2013 at 03:25 PM EDT
Sun-bleached straw hat? Check. Tanned toes digging into the sand of a Florida beach? Check. Cut-off T-shirt showing off those well-honed biceps? Check and, oh, yes
, double check.
It's a look that's helped make Kenny Chesney
country's favorite beach boy and win him a string of Entertainer of the Year trophies – and the title of People Country's Hottest Guy 2013.
But while the person staring out at the water this morning looks like the same fast-forward-living superstar who's been selling out stadiums and racking up hit singles for more than a decade, the singer admits he doesn't feel the same. And there's an intensity and thoughtfulness about him that hints at a man who wants to dig a little deeper.
"Sometimes things happen that just stop you in your tracks, and they change you," says Chesney, 45. "And that's what's happened to me. I'm a different person now."
For Chesney, it was the sudden death of longtime friend Kristi Hansen last year that made him take stock of his life. Hansen was part of a circle of friends he'd met back in the 1990s, when he was just on the cusp of stardom and began spending his downtime in the U.S. Virgin Islands.
"We came from all over and wound up there for our own different reasons," he says. "But they were all just like me. We were all a bunch of free spirits, all chasing something or running from something, and we all loved love and loved life and loved living it there."
Hansen's death from a brain aneurysm at age 35 – while six months pregnant with her first child – devastated the singer and inspired him to reevaluate his own life.
"You realize it could all end in a second," he says. "And if it all went away just like that, did I do everything I wanted to do, did I say everything I wanted to say?"
To continue reading the cover story and for much more on all your favorite country stars, pick up the new issue of PEOPLE Country, on newsstands Friday, May 31. Plus: Get free music from Brett Eldredge, Tyler Farr, Hayden Panettiere and more at people.com/free