Top 10 Kenny Chesney Songs — Country Music’s Most Important Modern Artists [No. 19]

Kenny Chesney's top songs are a mix of powerful ballads and carefree rockers, with more than a bite of emotion.

Few could argue any song on this Top 10 list is mere whimsy. The Tennessee native never released something meant to merely fill space on the radio. His best live hits are fun, but they don't stop at fun.

In an era of singers and songwriters bringing quarters to scratch the surface of emotion, Chesney showed up with gloves and a shovel.

This Top 10 Kenny Chesney Songs list is part of 25 straight Top 10 lists meant to celebrate country music's most important modern hitmakers. All month long, we'll release a ranking of the Top 25 with a list of his, her or their best songs.

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Kenny Chesney's Best Songs

Kenny Chesney released his first single in 1993, but it'd be several years until he scored a No. 1 hit.

"She's Got It All" peaked in 1997, but even after that, success would come mixed with failure. In fact, our list doesn't pick up until 2001 and the No Shoes, No Shirt, No Problems album.

There is simply not another artist who's more important in the 10 years that followed.

Not only did the future Country Music Hall of Famer (Class of 2025) find success on radio, he re-defined touring for country stars. Chesney — not Garth Brooks — was first to tour football stadiums.

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He created an almost Jimmy Buffett-like aura in which people would sign up for tickets regardless of new music. That lasted through the 2010s, and who knows? He just might surprise us with a dozen stadium dates in 2027.

Balance is important to Chesney's success as a hitmaker. After No Shoes, he teetered on becoming another sunshine party act, but songs like "Who You'd Be Today," "Don't Blink" and "I Go Back" added depth to his catalog.

Over the last 25 years he's remained an unpredictable music man with a catalog as dynamic as anyone who came before him.

The 58-year-old is No. 19 on our list of Most Important Modern Country Artists of today, but few doubt he's capable of a run in the next few years that could push him back into the Top 10.

Criteria: This list of the 25 Most Important Modern Country Artists was curated by Taste of Country staff, who considered hard data (charts, streaming numbers, ticket sales etc …), perceived influence, awards and recognition and (most important) recent releases. We zoomed in on who is shaping country music with popular releases today.

Artists who’ve not released an album or notched a hit song on airplay or streaming charts in the last three years need to show their influence in other ways. An example is Carrie Underwood, who’s not released a new album in four years but is the most influential voice on America’s most popular singing reality show.

No: 25 Riley Green's Top Songs | No. 24 Kelsea Ballerini's Top Songs | No. 23 Tim McGraw's Top Songs | No. 22 Blake Shelton Songs | No. 21 Eric Church Songs  | No. 20 Jason Isbell Songs | No. 19 June 19 | No. 18 June 20 | No. 17 June 21 | No. 16 June 22 | No. 15 June 23 | No. 14 June 24 | No. 13 June 25 | No. 12 June 26 | No. 11 June 27 | No. 10 June 28 | No. 9 June 29 | No. 8 June 30 | No. 7 July 1 | No. 6 July 2 | No. 5 July 3 | No. 4 July 4 | No. 3 July 5 | No. 2 July 6 | No. 1 July 7