The one of Kafir, I think, is the oldest. "A lot of surly teenagers think of themselves as being imprisoned by their parents," I thought. "But what if a guy's actual parents were his actual jailers." Then I drew this image and it was the springboard for creating the entire character. I kinda wish I'd kept the earring!
The early Tonya and the early Theo were both modeled on baristas that I knew. There is one even older drawing of Theo somewhere, which I can no longer locate.
The less said about my drawings skills in the spring of 2009, the better.