History YMMV / KennyChesney

** "You and Tequila": first cut by Deana Carter, then by cowriter Matraca Berg.

** "You and Tequila": first cut by Deana Carter, then by cowriter Matraca Berg.

** "When I Close My Eyes" was originally recorded by a little-known Epic Records artist named Keith Palmer, and later by Music/RestlessHeart lead singer Larry Stewart on his first solo album.
** Zig-zagged with ''two'' Mac [=McAnally=] songs: "Back Where I Come From" was Mac's only Top 40 country hit as a singer (he's had several more as a songwriter), but the song is more associated with Chesney, for whom it is a longtime staple in concerts. A live version appears on Chesney's first GreatestHitsAlbum. Chesney's version of "Down the Road" went to #1 compared to the #72 peak of Mac's original, but Mac got a guest vocal for Kenny's version. (What's more, Mac released both songs from the same album.)
** "Some People Change," a cut from ''When the Sun Goes Down,'' was later a Top Ten hit for Music/MontgomeryGentry off their album of the same name.
** Although Chesney wrote "I'm Alive," it was originally recorded by Music/WillieNelson on an album that Chesney produced.
** "El Cerrito Place" was originally released by Charlie Robison.
** "You and Tequila" is a Deana Carter cover.

** "When I Close My Eyes" was originally recorded by a little-known Epic Records artist named Keith Palmer, and later by Restless Heart lead singer Larry Stewart on his first solo album.

** "Some People Change," a cut from ''When the Sun Goes Down,'' was later a Top Ten hit for Montgomery Gentry.

** Although Chesney wrote "I'm Alive," it was originally recorded by WillieNelson on an album that Chesney produced.

* GrowingTheBeard: Chesney referenced this in an interview with ''Radio/BobKingsleysCountryTop40''. He said in the late 1990s, he saw several guys on {{CMT}} doing the same thing he was, and began questioning whether he was really the "hat act" persona he'd been playing to that point. Over the next several years, he began to move to party anthems, and then again to acoustic ballads.

* GrowingTheBeard: Chesney referenced this in an interview with ''Bob Kingsley's Country Top 40''. He said in the late 1990s, he saw several guys on {{CMT}} doing the same thing he was, and began questioning whether he was really the "hat act" persona he'd been playing to that point. Over the next several years, he began to move to party anthems, and then again to acoustic ballads.

** "When I Close My Eyes" was originally recorded by a little-known Epic Records artist named Keith Palmer, and later by RestlessHeart lead singer Larry Stewart on his first solo album.

* GrowingTheBeard: Chesney referenced this in an interview with ''Bob Kingsley's Country Top 40''. He said in the late 1990s, he saw several guys on {{CMT}} doing the same thing he was, and began questioning whether he was really the "hat act" persona he'd been playing to that point. Over the next several years, he began to move to party anthems, and then again to acoustic ballads.

** "You and Tequila" is a Deana Carter cover.

* CrowningMomentOfAwesome: "Don't Blink" set a new record for highest debut on the country music charts, entering at #16. Even more impressively, it was the ''second'' single from that album. However, this trope quickly got subverted when GarthBrooks's "More Than a Memory" debuted at #1 only a week later. Yes, you read that right.
* CrowningMomentOfHeartwarming: Chesney's mom and aunt used to record as The Grigsby Twins. They sing backup on a cut on ''Real Good Tan''.

** In a self-cover up, Chesney re-recorded his 1994 single "The Tin Man" for his first GreatestHitsAlbum and released the new version in 2001. The re-release has the distinction of being his only single release of the 2000s not to reach Top 10.