Well its been a little while since I got around to posting here! Here's a design I did a little while ago when I was in a Tolkien sort of a mood. Bilbo and Gollum seemed to be opposite enough in their characters to make this sort of idea work. And of course it ends up that both are needed to complete the story of the ring.
As always this design is available on T-shirts, iPhone cases and all sorts of other stuff at Redbubble and Society6. Check out the Doodle Dojo Store for all the info an lots of other designs.