These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Zig-zagged with "Some Days You Gotta Dance." He originally recorded this while in The Ranch, but the more famous version is by the Dixie Chicks. However, he played guitar on their version.
Inverted with "Stupid Boy." Sarah Buxton co-wrote it and recorded her version around the same time as Urban, but her version was not available commercially until after Urban's version peaked.
He has done this twice with Radney Foster songs: "Raining on Sunday" (which appeared on Urban's Golden Road) and "I'm In" on Defying Gravity. The latter was also released by The Kinleys before Urban covered it. Interestingly, Foster's originals are consecutive tracks on the same album (his 1998 release See What You Want to See).
"Making Memories of Us" was first recorded by Tracy Byrd. Rodney Crowell (who wrote it) and Vince Gill later recorded the song as part of their side project, The Notorious Cherry Bombs, before Urban released his rendition.
Ending Fatigue: The three-minute acoustic coda to "Stupid Boy". It wouldn't be so bad if the song weren't a midtempo ballad.
He also vamps for a good two minutes near the end of "Everybody", complete with string section and French horns.
Hell Is That Noise: The sharp whistle blow right before the first chorus to "You Gonna Fly". You're not a traffic cop, Keith.
Tear Jerker: Several of his songs in general, but the one song his fanbase is known for weeping like a baby to is "Desiree" back from his days in The Ranch.