When we created the 2014 list of 100 Things to Draw When You’re Bored, I had the idea to make several prompts based on the idea that really terrible people probably still love ice cream. I added names to the list, not yet considering what I have since then discovered: I don’t know what a lot of historical bad guys look like!
This drawing still won’t give you an accurate portrait of Machiavelli, not least because I refuse to draw his proto-mullet. (Really. It’s awful.) Here, however, is the rest of Machiavelli, for the prompt “Everybody Loves Ice Cream – Machiavelli” (#65):
Next up, meanwhile, is a trio of guys I would recognize anywhere. And dammit, Walter, I drew them for the prompt “Bowling Pin People” (#69):