"Down the Road Tonight" - in the tradition of "list" songs (think REM's "It's the End of the World..." or Billy Joel's "We Didn't..."), except Carll's list is really fucking great:
http://www.youtube.com/watch?v=A5OhovnEFDk

"It's A Shame" - turns a pretty standard topic (regretting lost love) into something really new, just by being careful w/words:
http://youtu.be/6mj6XcRNxCU

"Bye Bye Baby" - good example of what straight simple can do - there's nothing fancy here, just a great song:
http://youtu.be/e6-YgIlySms

edit for a bonus:
http://youtu.be/07E02k4cj4s - "KMAG YOYO" - great performance, this has sort of become his "hit" recently, along with another tune, "Never Be Another Like You" - this is a story-telling tune even if it does feel like a straight "Suburban homesick" rip

-thebigfunk

~ i could still snort you under the table ~