* BlackSheepHit: He has three typical modes: beachy Jimmy Buffett-esque tunes, introspective acoustic ballads, or arena rock. His two biggest hits, "The Good Stuff" and "There Goes My Life", are none of the above. (They're still ballads, but in a markedly different and more mainstream style from his usual ballads such as "Down the Road" or "You and Tequila".)
* BreakthroughHit: "She's Got It All" (1997) was his first #1 on Billboard and the song that helped kick-start his career. A couple years later, "How Forever Feels" pushed him from rapidly-ascending second-tier to A-lister.
* VindicatedByReruns: "She Thinks My Tractor's Sexy" was only a modest #11 hit, but it remains one of his most popular cuts by far and received heavy airplay even after it was long gone from the charts. Likewise, his cover of Mac [=McAnally's=] "Back Where I Come From" is sometimes heard on radio even though it was not a single, thus obscuring the fact that ''Mac's'' version was a single.
* WhatCouldHaveBeen: He was scheduled to film the video for the re-release of "The Tin Man" at the World Trade Center on September 11, 2001, but the shoot was held up due to a delay in shipping the equipment.