This page, in panel three, contains what I think is my best drawing of Zip’s shadow. It’s one of my favorites.
Before I’ll start drawing a character in my comic, even very minor characters who may only appear in a panel or two, I’ll usually do a bunch of sketches in my sketchbook and make notes of parts of the drawings that are working and I’ll want to continue, and parts of the character drawing which I’ll want to avoid. From that point on though, I don’t obsess about sticking to those early “models” and just accept that the characters are going to evolve (and hopefully get better) as I keep drawing them over and over and discover thier strengths and weaknesses.
Mr. Shadow is a fun character in that one of his strong points is that I can draw him as a round-headed blob or a distinct entity on essentially a panel by panel basis according to his role in each particular picture. For instance, if he’s not speaking or interacting with the other characters, I can draw him in as a blob and completely de-emphasize him. The challenging part about him is that when he is speaking I have to work the entire composition of the panel to accommodate him, which can be tough since he’s someone who spends most of his time on the floor. I think solving problems like that is what’s inspiring though, so it’s all a good thing.