Step 1: Pumpkin Shopping, Permanent Marker
You need a pear shaped, head-sized gourd. It can be shaped like a pear or a lightbulb, as long as it's got a nice round chunk where one might keep one's brains, and a narrower area that might server as a jawbone. Often a pear-shaped pumpkin will be a bit skewed to one side: these are especially good for our sinister purposes.
Pick up the candidates. Recite some Shakespearian Yorick-related verses. Think "skull." If at some point this process gives you either the willies or the creeps, then you've probably found the right pumpkin.
Take it home and rub your hands together, cackling, and bust out your permanent marker.
Draw out your shapes, using photos, toy skulls, or actual skulls if you have them laying around.

























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Actually, any fruit or vegetable that's solid has a bit of an advantage over a pumpkin, because you can get the relative depth closer to reality. A pear would work great because of the fact that it is... wait for it... pear-shaped. Of course it's not easy to find a pear the size of your head.
"what does it say in the orange writing on the second picture of the last step?"
...I lifted that photo (of one of my skulls from a few years back) from extremepumpkins.com, rather than digging it up on my machine: Pure laziness really. And I can't quite make out what it says either; maybe it's just a funky dental pixellation?
But wait, there's always Thanksgiving! How about a skull carved into the surface of your turkey? Add that missing spark or horror to the feast! Guaranteed alienation from family and friends!