After getting inducted into the Country Music Hall of Fame, and with his 58th birthday just around the corner (March 26), some fans might be wondering if Kenny Chesney plans to retire or slow down.
Chesney recently spoke to People about about retirement and when he might call it quits. Thankfully, the country music legend with 30 No. 1 songs under his belt is still going strong.
“I love creating. That’s what I’ve always done, so I don’t see [slowing down] in my near future,” he told the publication.
Speaking on Taste of Country Nights in a recent interview, fellow country star Lainey Wilson told host Evan Paul that she had 2026 almost fully mapped out already. Chesney’s looking even farther ahead.
“My life is already so planned out. I know what I’m doing in 2027!” he told People.
Plus, the musician feels most alive when performing to a stadium crowd.
READ MORE: Kenny Chesney Recalls Losing His Hair as a Teen
“I love what I do. I love making music and I love being on that stage, more than any place in the world,” he shared.
With Chesney being single and having no kids, he really doesn’t have anything holding him back from playing shows until he’s Willie Nelson‘s age. (Nelson’s 92 as of writing, if you’re wondering.)
Will Kenny Chesney Return to the Sphere in Las Vegas?
Yes! Chesney’s 2025 Vegas Sphere residency was so popular that he’s already signed up for more dates in 2026, beginning next year in June.
Kenny Chesney’s Love for Beach Music
Chesney credits his own mother for instilling that beachy vibe into the “No Shoes, No Shirt, No Problem” singer.
“You can give my mom credit on this one, too — I’ve always been a fan of feel-good music. We would go to the beach as a kid, and she loved beach music, and she just loved to feel good and loved to make other people feel good. So that’s always been infused in my thinking when I either listen to music or if I’m creating it,” he explained to People.
25 Best Kenny Chesney Songs That Prove He’s Country Music Hall of Fame Worthy
What truly separates Chesney — a 2025 Country Music Hall of Fame inductee — from other artists is his third act. Six of the 25 songs on this list of Kenny Chesney’s best were released after 2010. It’s there he took some of his biggest risks, rewarding fans with some of the greatest lyrical moments and sounds of the 21st century.
We ranked the Top 25 Kenny Chesney songs using chart data, streaming and airplay numbers and staff/reader opinion. The year listed alongside the title is the year it was released as a radio single. The No. 1 song on this list exemplifies the best of what the Tennessee native is capable of.
Gallery Credit: Billy Dukes
PICTURES: See Inside Kenny Chesney’s Spectacular $11.5 Million Tennessee Estate
Kenny Chesney has sold his 4-bedroom, 9-bathroom, 12,599-square-foot hilltop estate in Tennessee for $11.5 million, and pictures show an opulent Mediterranean villa that is lavish even by the standards of other celebrity mansions.
Gallery Credit: Sterling Whitaker
