A little while ago, I did a "How to Draw Doug" installment in a Super-Fun-Pak, and then followed with a blog post showing an older "How to Draw Doug." I knew this older one wasn't the first one I'd done, but I couldn't find an earlier one in any Super-Fun-Paks.
I finally remembered where I first drew a "How to Draw Doug": It was in a Tom the Dancing Bug comic book, published in 1995. The comic book was a compilation of published strips, but I drew up original material for the inside front cover, including this: