Jonathan Coulton is quite the geek rocker. You may have sen him referenced by or appearing with John Hodgman. I just started listening to him recently, but I do quite enjoy his songs. You can acquire many of these finely crafted pieces of music for free by downloading them from his website. If you like them, throw a little cash his way.
If you'd like to see him appear in Lexington, then demand that he do so here:
Mr. Coulton suggests in this article that he will attempt to perform in any city with more than 100 requesters. As we are now at 13 in Lexington, KY, we only have 87 more to go! Yay! The Louisville group is a little closer 100 so you might also click there if you don't mind the drive.