25 Best Kenny Chesney Songs That Prove He's Hall of Fame Worthy

Kenny Chesney's best songs are rockers, ballads, anthems, blasts of nostalgia and reminders of what it feels like to see him live in concert. The best Kenny Chesney song is all of these things.

The East Tennessee native debuted in 1993, but would need several years — and several radio singles — to find his footing. Even then there was a sense that he was still figuring it out across four studio albums.

His 2002 No Shoes, No Shirt, No Problems album changed everything.

Lifetime, Chesney has 33 No. 1 singles on the Billboard Country Airplay chart.
He has four CMA and four ACM Entertainer of the Year awards.
On March 25, Kenny Chesney was announced as a 2025 Country Music Hall of Fame inductee.

Just two of the songs found on this list of Chesney's best songs were released in the 1990s, but that first act was important in shaping the artist he'd become. The 2000s were his decade in country music. Each single seemed to breathlessly race the last up radio charts. Concert tickets and albums sold like they came with the meaning of life!

Anthems like "Summertime" and island vibes like "When the Sun Goes Down" may be what Chesney ends up being remembered for, but the true power of his catalog is in ballads like "There Goes My Life" and "Don't Blink." The songs that married meaning to melody?

These were truly special.

"Anything But Mine" makes that short list, and thus ends up near the top of this list. "Never Wanted Nothing More" and "Boys of Fall" do, too.

Get our free mobile app

A third act in the 2010s found Chesney reaching inward for his most stunning vocal performances. "Come Over," "You and Tequila" and "El Cerrito Place" are a few examples. Not every song worked on a commercial level, and some made terrible live songs, but they were still brilliant risks.

Then, on occasion, Chesney would put all the parts together. The No. 1 song on this list is a great example of what that sounds like.

25 Best Kenny Chesney Songs That Prove He's Country Music Hall of Fame Worthy

Kenny Chesney's best songs come from three distinct eras of his career. There are early career singles like "How Forever Feels" and mid-2000s hits like "When the Sun Goes Down," "Summertime" and "Anything But Mine."

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