TheNovak wrote:
Much awesomeness

How do you do those? Do you make some kind of template from the prints, or is it just free-hand knifin'?
I made a template from the prints. Doing it freehand would be... damn, I dunno. Pretty near impossible, but if I say it can't be done someone will do one freehand just to spite me.
The templates are actually up there too, since I let the IRC crowd drool on them while waiting for my camera to return so I could get real pictures. Feel free to carve away if you want. The sal one isn't all that hard to do; the walky&joyce one will drive you batty
http://puetzk.org/tmp/manyfaces-template.png
http://puetzk.org/tmp/timetogether-template.png
I made them in gimp with the following steps:
darken the original quite a bit (so that when I'm stencilling I'll have the feeling of working against black)
add a new solid black layer, and hide it (this is so I can flip it betwen looking at the stencil on the drawing by showing or hiding this layer)
add a layer of orange candle-y color, with a transparent mask
pick the mask for the orange layer as my target, and take a brush to adjust it's opacity. Tweak until I'm happy with it.
Mostly I try to follow edges, but it's important to realize that you can use a black edge just as well as a lit one (Sal's ears, Joyce's left leg, etc). This lets you leave enough pumpkin in place that the whole thing doesn't just disintegrate

I often end up doing a sort of reverse color image, where the shadows are the parts that end up being cut out and lit. That seems to work well in general for picking a width of the cut that looks natural.
As far as actually carving goes, there's only two real tricks to it. One is to punch a starting hole through everywhere you'll be sawing out before you cut anything away - ie, while the pumpkin is still strong enough that you don't break anything pushing through. The other trick is that on some of the detail work isn't actually sawed all the way through - if you use a sharp knife you can just cut the skin away, and the pulpy stuff behind it is pretty translucent. It can be a neat effect on it's own (ie, Sal's gloves are a darker than her arms), and it also lets you put in details while leaving enough pumpkin intact that the thing doesn't just disintegrate (I did Daniel's leash and Joyce's hand holding it this way for that reason).