So I only carved one jack-o'-lantern this year --- it's a measure of how excited/worried I am about this election that Halloween has almost completely slipped my mind this year --- but I'm really pleased with the way it turned out, and I did remember to take lots of pictures at different stages of the process.
I decided I wanted to carve it in the likeness of Gollum from The Hobbit and The Lord of the Rings, as he appears in the "Lord of the Rings" movies.
This is the picture I worked from:
This is my negative-space interpretation* of that picture, after I had finished transferring it to the pumpkin by taping my drawing to it and poking zillions of little holes all along every line.
Here, I have recreated the negative-space drawing on the pumpkin by tracing over the pin-holes with a Sharpie:
And here is the finished project:
Finally, here it is all lit up:
*Drawing from the movie still, I actually produced a line drawing first, and then turned that into a negative-space drawing so that my lines would actually show up on a jack-o'-lantern. It occurs to me now that I ought to have scanned the original line drawing, but whatever.