Black Sheep Hit: 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".)
Breakthrough Hit: "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.
What Could Have Been: 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.