Place all 16 plastic cups on a baking sheet or on your serving plate, for easy transport. Leave the lids off the cups.
Orange Layer:
Place the pudding powder in a mixing bowl. Add milk and whisk for 1 to 2 minutes, or until completely dissolved.
Pour the pudding into each of the plastic cups, filling them about 2/3 of the way full.
Transfer the cups to the refrigerator and chill for 15 mins, or until the pudding has set up.
Black Layer:
Place gelatin in a medium mixing bowl and pour cold water over the top. Stir and let sit for 2 minutes.
Once the gelatin has completely absorbed into the cold water, pout the boiling water over the gelatin and whisk until the gelatin is dissolved.
Add the sugar and vodka. Whisk to combine.
Dip the toothpick into the black food coloring and then into the gelatin mixture. Whisk to distribute the food color.
Pour the black jello into the plastic cups, filling them the rest of the way.
Refrigerate for at least 2 hours, or until the shots are set. Cover with plastic lids.
Notes
You don't need very much gel food coloring at all, whatever sticks to the toothpick is good.If you're using liquid food color add a few drops at a time until your reach a solid black color.