- Covered Up: Generally averted since Keith writes about 95% of his material, but it's happened a couple times:
- "A Little Less Talk and a Lot More Action" was originally recorded by Hank Williams, Jr..
- He covered Sting's "I'm So Happy I Can't Stop Crying" as a duet with the original artist. The duet outpeaked Sting's original on the pop charts.
- A strange zig-zagging came with "I Can't Take You Anywhere". Keith originally recorded the song, but co-writer Scotty Emerick released it as a single two years later. Emerick's version featured a guest vocal from Keith.
- Funny Moments: "Red Solo Cup".
- Signature Song: "Should've Been a Cowboy", "How Do You Like Me Now?!", "Courtesy of the Red, White & Blue", "Beer for My Horses", etc.
- Tear Jerker:
Oh Santa, if you can't find me
- "Santa, I'm Right Here", from his first Christmas album, about finding a note from a poverty-stricken child:
We're livin' out here on the street
But I'll be watchin' for you, you're not gonna forget me, are you
Daddy says he knows you'll try
But we might be too hard to find this year
Oh Santa, I'm right here
- "Cryin' for Me (Wayman's Song)", a sincere tribute to basketball player/jazz musician Wayman Tisdale.
- What An Idiot: The video for "A Little Too Late," wherein he attempts to seal (literally) his ex-girlfriend in an enclosed wall in the dark, dank basement of his home. He is so focused on getting even with her ... he fails to realize that he is actually sealing himself in the room until after he has placed the last cement block of his wall. The girlfriend escapes safely and leaves ... presumably to call the police, while Keith tries to apologize and call for help.