This is an old one that I had thought disappeared until I discovered again tonight. I was mostly thinking of Sienfeld and Puddy when I did this one. Hopefully you guys think it's worth posting.
Commentary: I skipped over my usual flash ->Photoshop cleanup combo on this one, and just went "balls out" with photoshop brushes right over the rough. The edges tend to get a little wonky, but it helped give the whole illustration a more traditional feel.