Goofy Buck-Toothed Smiling Jack-O-Lantern Face

From pumpkin to porch

1. 1

   Pick your pumpkin and open the lid

   Choose a tall, round pumpkin with a smooth front and a sturdy stem. Cut a lid around the stem at an angle so it rests without falling in, or cut a hatch in the back if you prefer to keep the front clean. Scoop out the seeds and pulp, then scrape the inside of the front wall down to about one inch thick. A thinner wall makes the teeth much easier to carve and light later.

2. 2

   Transfer the grin and eyes

   Sketch or tape on a wide, curved mouth that stretches nearly ear to ear, and mark two tall crescent eyes above it that curve up like happy squints. Inside the mouth, draw two big rectangular teeth hanging from the top edge with a small gap between them. Let the eyes be a little uneven on purpose, since that lopsided look is what sells the goofy expression. Poke through the outlines with a pin or awl so you have a dotted guide to follow.

3. 3

   Carve the mouth and keep the teeth attached

   Start with the mouth since it is the largest opening and you want the pumpkin at full strength while you work it. Cut along the outline with a small carving saw, held straight into the wall, and remove the plug in pieces if it is large. Leave the two teeth uncut so they stay joined to the top edge of the grin, forming natural bridges that hold them in place. Take your time around the base of each tooth so you do not snap it loose.

4. 4

   Thin the backs of the teeth so they glow

   From inside the pumpkin, gently shave the back of each tooth with a loop tool or spoon so the flesh gets thin but is not cut all the way through. The goal is a dim orange glow through the teeth rather than a dark silhouette. Check often by holding the pumpkin up to a window, and stop while there is still solid skin on the front. This peeled look is what makes the buck teeth read as playful rather than menacing.

5. 5

   Cut the crescent eyes last

   Now carve the two curved eyes as clean full cutouts so they shine bright above the grin. Cut the inner points of each crescent carefully so the tips stay crisp and do not tear. Because these are your last big openings, the pumpkin wall is already weaker, so support the flesh with your free hand as you finish each curve. Clean up any ragged edges with a paring knife for a smooth outline.

6. 6

   Light it and take the photo

   Drop in a battery LED tea light or a small LED puck rather than a flame, since the thinned teeth and open eyes will glow beautifully and safely. Set the pumpkin on a step or porch at dusk so the warm light stands out against the fading sky. Rotate it until the goofy asymmetry looks its best from the front. A light coat of petroleum jelly on the cut edges helps slow drying if you want it to last a few extra days.