Chronicle Pirates
Last year I was asked to illustrate a story by a friend of mine (the same who made Second Youth with my help).  These were two of the more minor characters (at least compared to the other less comical ones), but they were the more fun to design since the others were more serious and therefore more detailed.  I had free range on the pirates so there was a lot more fun to be had with these guys.  I was watching Lord of the Rings special features when I got the idea for the giant meat cleaver of a sword.