* CoveredUp:
** "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.
** 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 Montgomery Gentry.
** Although Chesney wrote "I'm Alive," it was originally recorded by WillieNelson on an album that Chesney produced.
** "You and Tequila" is a Deana Carter cover.
* 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.
* HilariousInHindsight: In 1999, he had a #1 hit with "You Had Me from Hello", inspired by a line spoken by Creator/ReneeZellweger in ''Film/JerryMaguire''. Six years later, Chesney was briefly married to Zellweger.
* SecondVerseCurse: The radio edit of "When I See This Bar" cut an entire verse and some lines from the coda.
----