100 Greatest Men: #57. Kenny Chesney

100 Greatest Men: The Complete List

After many years as a mid-level country artist, Kenny Chesney fused arena-size country with Caribbean rhythms to become one of the genre’s biggest stars of the 21st century.

Born and raised in East Tennessee, Chesney didn’t seriously start pursuing music until he was in college, despite being an enthusiast his entire life.   While continuing his studies, Chesney played in a bluegrass band and for tips at a Mexican restaurant.  He managed to finance a demo album and moved to Nashville in 1991.   He played at a local honky-tonk called the Turf, and eventually landed a publishing deal in 1992 that led to a record deal with Capricorn in 1993.

His debut for the label, In My Wildest Dreams, found little success, but it laid the groundwork for a new deal with BNA Records.  His second set, All I Need to Know, put him on the map.  Throughout the nineties, he slowly built a career at radio and retail, as his songs inched higher on the charts and he moved from gold, to platinum, and then to multi-platinum sales by the end of the nineties.

Still, there was little to indicate that he was about to explode into superstardom.  But as his live shows gained greater attention, Chesney began to incorporate Caribbean sounds into his music, styling himself as an island singer in the same vein as Jimmy Buffett.  Through stronger song choices that helped repair the novelty act image that had been created with hits like “She Thinks My Tractor’s Sexy”, Chesney began to earn critical acclaim for his work.

By the mid-2000’s, Chesney was the biggest act in country music, selling millions of copies of his albums and more concert tickets than even the biggest pop and rock acts of the day.  He dominated the awards circuit, and even managed to sell big numbers of indulgent side projects like Be Who You Are and Lucky Old Sun.

Today, Chesney remains a top concert draw and a core radio act. He is currently prepping another studio album and a co-headlining tour with Tim McGraw.

Essential Singles:

  • That’s Why I’m Here, 1998
  • The Good Stuff, 2002
  • Anything But Mine, 2005
  • Who You’d Be Today, 2005
  • Beer in Mexico, 2007
  • You and Tequila (with Grace Potter), 2011

Essential Albums:

  • I Will Stand, 1997
  • No Shoes, No Shirt, No Problems, 2002
  • When the Sun Goes Down, 2004
  • Be as You Are: Songs From an Old Blue Chair, 2005
  • The Road and the Radio, 2006

Next: #56. Bobby Bare

Previous: #58. Carl Smith


  1. You mentioned it in the article, but I think “She Thinks My Tractor’s Sexy” should have been included as an essential single. That’s one of the first songs that I think of when I think of Kenny Chesney, and although it is completely ridiculous, it’s one of my favorites of his.

  2. I’m actually surprised you have Kenny this high on the list. Considering the amount of hate he gets on various sites like this, I thought he would have been lower.

  3. I disagree with “Who You’d Be Today” as an essential single, but I ESPECIALLY disagree that “Easy Money” is an essential album….mostly because that’s not even one of his albums. :^\

  4. I won’t engage in “Chesney Cheesing” here, but he’s not really a favorite of mine. That said, he really did well on “I’d Have Done A Lot Of Things Different”, which is one of the more underplayed songs on country radio thus far this century (IMHO). Given that, I think #57 on the list is very respectable.

  5. I’m wondering if you’ll get a lot of flak for his high ranking, but I won’t argue with you. I actually like a lot of his stuff. I can’t listen to his music for more than an hour or so because there’s just not a lot of variety, but when he’s good (You and Tequila, Anything but Mine, What I Need to Do, Better as a Memory), he’s so good!

  6. If I had to listen to a Chesney song, it would be a song he wrote with Skip Ewing, “You Had Me From Hello”. Just don’t care for his voice. I had his first greatest hits album but gave it away.

  7. I think I would have Kenny a bit higher on the list than this – somewhere in the 30s.I’m not a big fan but his impact, for better or worse, has been undeniable

  8. His ‘Lucky Old Sun’ album is a definite favorite of mine. Sure it’s mostly mellow but it’s a killer collection of songs. The title track duet with Willie Nelson is fabulous.

    Chesney’s impact on country music is, like Paul said, undeniable. He’s taken the Garth Brooks touring model to the next level by turning concerts into events and turning Gillette Stadium in Foxboro, Ma (near where I live) into a money machine.

    In the last twenty years, and this is saying a lot, I don’t think there is a country song I hate more than “She Thinks My Tractor’s Sexy.” On multiple occasions, I’ve run into people who know so little about country music, they think that song represents the genre as a whole.

    On my college radio station they ran an anti-country music PSA (I removed it for being more than offensive – they didn’t make fun of any other form of music) and used that song to further humiliate those who take country music seriously. This was also coming from people who feel no one should overdose on country music but that’s another story for another time.

    It’s funny I had a conversation with someone the other day who asked me if I was a Chesney fan. I said yes, but I mentioned that I knew him back when (like when he brought his mother on stage when he won the Top New Male Vocalist ACM Award in 1997 or when his “Me and You” video was played every ten seconds on CMT in 1996) but didn’t give examples. Dead serious, the person came back to me and said “oh, when he was married to Renee Zellweger?” Yes, I thought, “back when” was 2005.

    Anyway, I’ve been a fan of his music since I began listening to country. I was surprised to see him so high on the list but there really isn’t anyone who can match his mega-success right now apart from Taylor Swift, but that’s because she has the whole “pop world” behind her, too.

  9. I find it funny that some people really dislike She Thinks My Tractors Sexy yet are ok with Big Green Tractor, She’s Country, Country Girl Shake It For Me, and the list goes on.

  10. I think the Essential Singles list is a nice sampling of some of Chesney’s best work. “You and Tequila” remains my favorite Chesney single by a mile. I personally would keep “Who You’d Be Today” on that list as well.

  11. I would personally like to add “She’s Got It All”, “Back Where I Come From” and “You Had Me From Hello” to the essential singles collection.

    I love 90’s Kenny Chesney with tracks like “When I Close My Eyes”, ” Fall in Love”, “Me and You”, “The Tin Man” and “She’s Got It All 10x as much as most of his modern sounding stuff, save Tequila. Partly because his 90’s work actually sounds country and partly because I simply view it as better material.

  12. “I find it funny that some people really dislike She Thinks My Tractors Sexy yet are ok with Big Green Tractor, She’s Country, Country Girl Shake It For Me, and the list goes on.”

    Word. Sadly, “She Thinks My Tractor’s Sexy” proved to be a blueprint for the decade that followed (and beyond).

  13. I’m surprised to see Kenny ranked 20 points higher than Brad Paisley, who I consider a superior artist. KC has one of the least musical voices — flat, hazy, toneless — and when he has subpar material, he’s completely dismissable for me. (In contrast, I could listen to Ronnie Dunn sing the proverbial phone book.)

    I saw Kenny only once live (at Farm Aid about six years ago) and thought J. Mellencamp outperformed him, so have no idea why he’s the alleged arena god.

    But when he gets hold of a certain kind of song, that unpolished quality in his voice is an asset. Those are usually the “life lessons” sort of songs, of which several are on the essential list. I too would add “Better as a Memory,” which I consider as good as KC gets. That song really got to me (and still does).

    He totally loses me with material like “Reality,” “Living In Fast Forward,” “Summertime” (one of the lamest seasonal cash-in songs), and about half the Carribbean stuff. I guess what I’m saying is it takes a pretty profound lyric for me to appreciate Kenny, but he can deliver that material as well or better than anybody. Sadly, that’s only about a quarter of his radio output. (I do not own a KC album.)

    I’m really curious now about where Tim McGraw’s going to land on the list.

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