* BlackSheepHit: For a long time, "Why" was both his only love ballad and his only #1 hit.
** Inverted with "Don't You Wanna Stay", his first hit at AC.
** In addition, his highest charting hit on the Billboard Hot 100 to date is "Dirt Road Anthem," a country-rap song, which is a very different style from his other songs.
* ChartDisplacement: "Hicktown" is still one of his most famous songs despite only hitting #10.
* KeepCirculatingTheTapes: A few days after its release, "Take a Little Ride" had the line "Grab a little Shiner Bock" replaced with "Grab a couple Rocky Tops", as he had just signed an advertising contract with Coors. You might find an occasional station still playing the "Shiner Bock" version, but most online outlets have only the "Rocky Tops" version.
* MissingEpisode: Narrowly averted with ''Relentless''. There was a fire in the studio where the masters were held, but it stopped just shy of said masters.
* WhatCouldHaveBeen: He was signed to Capitol Records in 2001, but never released anything for them.