These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
"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 Greatest Hits Album. 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 Willie Nelson on an album that Chesney produced.
"You and Tequila" is a Deana Carter cover.
Growing the Beard: 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.