This started out as a wreath-like figure that gradually grew into a more sinister fellow. Everything was done in Photo-Paint while working on a Wacom tablet (reference photos and character progression are show below the main illustration).

The trick was keeping the background from conflicting with the character and his shadow. This was done by carefully shading bricks and keeping the clouds very subtle and painting them carefully so they weren't distracting from the figure itself while still adding to the general feel. The moon was created with a circular mask that was offset to "expose" the white layer beneath.