Breakthrough Hit: Although his first album went platinum and produced three big hits (the #1 "But for the Grace of God" and the Top 5 hits "Your Everything" and "Where the Blacktop Ends"), he didn't really break through until "Somebody Like You". A fairly long hiatus between "Blacktop" and "Somebody Like You" helped, as did the fact that the latter was named by Billboard as the biggest country hit of the 2000-2010 decade.
Creator Breakdown: Having just come out of rehab before Golden Road, Urban shows a great deal of optimism on that album. Be Here and Love, Pain & the whole crazy thing continue with the optimsm, but also show the demons creeping back in on tracks like "Tonight I Wanna Cry". After another trip to rehab and his marriage to Nicole Kidman, he has taken refuge mostly in uptempos about how happy he is to be in love.
Keep Circulating the Tapes: For some reason, Greatest Hits: 19 Kids (the re-release of Greatest Hits: 18 Kids) isn't on iTunes, so this is the only way to get the single version of "You Look Good in My Shirt". Likewise, the re-recorded radio version of "Where the Blacktop Ends" was not commercially available until 18 Kids.
Throw It In: "Little Bit of Everything" is a double example. The "stuttering" ukulele part was thrown in by Nathan Chapman due to the demo track also using a ukulele, and it was chopped up at Urban's request to mix it up a little. Also, the bass line is played on a synth because the first two bassists that they contacted were unavailable, and even though Urban can also play bass, Chapman suggested using a synth instead. The latter doubles as a Serendipity Writes the Plot.