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.

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

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.

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.