Happy Tree Friends Evil Fliqpy (Flippy) Halloween Pumpkin Carving jack-o-lantern.
I did this a couple of years ago for newgrounds pumpkin carving competition. We had to constrain the carving material to something on the site, and since Happy Tree Friends was originally a flash video on the site, even though it no longer is it was still eligible.
I think I won 2nd place for this, which was still good. Flippy is basically a green skinned war veteran bear who suffers from ptsd, and whenever something happens that reminds him of the war he mutates from a cute happy bear to an evil toothy psychopath who goes on killing sprees.
I have always loved to carve pumpkins. I did all of this entirely with just a carving knife - the teeth are part of the pumpkin, they have not been "inserted" into it - and the ears are the hollows of the eyes - I even added the bags under the eyes.
I used the round disc from inside the microwave to be able to rotate it evenly, and I used an old hat and put a logo on it to represent his beret. You can see my reference image for him here:
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