By skyforbes 
My daughter's three, and utterly obsessed with Guybrush Threepwood. She wanted him on a Jack-o'-lantern, and there ended up being so much room that I put the whole main cast on there. (Yeah, I'm a bit of a fan too.) Here's a gallery of all five characters I managed to fit on.
Pro tip: wood carving tools are amazing for Jack-o'-lanterns! I've always only used a knife in the past and my Jack-o'-lanterns were always amateur messes. So I was really happy with how this turned out.