I'm not much of a painter, though so I decided to try using Sculpty. I started with the nose, I was intentionally making it over sized for the pumpkin I had, and I have to admit I was thinking of Yubaba from Spirited Away when I started.

I made the center bit first and then cut open a sphere of clay, hollowed the halves out and attached them. I think it came out pretty good, it's a little uneven almost like one nostril is flared or the nose is twitching, and it's nice & pointy.
After I had the nose done I started working on the eyes. I started with another ball of clay that I cut in half and shaped, then I rolled out a piece of clay and pressed around the top of the eyes and then trimmed it down to look like a eye lid. It looked a little top heavy at that point so I rolled out another piece of clay for the under lid.

For the Iris I ended up using the top of a bottle of nail polish, because I couldn't figure out another way to make the iris really round. As it was the iris is too small and it looks kinda creepy.

I used the same trick for the pupil, only this time it was a bottle of Tacky Glue.
I wanted to do a really cool, half snarl for the mouth but I ran out of time, so I just made them big and pouty. I was pretty much ready to bake them but I occurred to me that I needed a good way to secure them to the pumpkin, so I used fatheaded jewelry pins and extra bits of clay to secure them.
Once they were baked it was time for paint!

I started with a base coat of white on everything, and started with the lips which I painted an out-of-the-tube red. I wanted a really brilliant blue for the iris so I used nail polish, and for the eyeshadow I mixed a slightly red violet, I really wish I'd had some fine glitter to use instead, but oh well. I also had this idea to use thin costume feathers for the eye lashes but they didn't workout so I painted kohl on instead.

The pumpkin itself, I painted half white & half black, and then I cut a big handful of worsted weight black yarn into approximately 8" lengths, smeared the black part of the pumpkin in tacky glue, folded the strands in half, and used tweezers to place the middle along the center seam of the pumpkin.

I also used some rug cotton I got for free from the BMFA barn sale a few years ago to make the core of the bun, painted it black, applied the tacky glue, and used more yarn to cover it.
The end result...

I like the concept for this piece, but some aspects of the execution need work. When I get some more free time I plan to try again with a styrofoam ball.