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):

Everybody Loves Ice Cream - Machiavelli_wonderstrange


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):

Bowling Pin People_wonderstrange



Ann D'Angelo is a dedicated drinker of diet Coke who has never spotted a thrift store she didn't want to visit or an item she didn't want to alter. Check out Ann's shop.


sarah · August 20, 2014 at 12:39 am

Ice cream is DEFINITELY greater than infinity.

and I love your bowling pin people!! How perfect to Lebowski them <3

    Charlie · May 8, 2016 at 4:12 am

    Me too!!

Charlie · May 8, 2016 at 4:10 am

I love the idea of everything!!!!!

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