This two-sided jack o' lantern was inspired by a photo I saw online that looked similar to the carved-into face on the right. Since the pumpkin I chose had a flat surface, I used a Dremel, X-Acto blades, and a lemon zester to carve a two-dimensional version of Jack's face on that side. Then I drew a face on the other side, used the Dremel to score the lines, and cut the pieces out with a small saw.
See photos 2 and 3 for more!