In a large mixing bowl with an electric mixer on low, mix together the pudding mix and milk. The mixture will be quite thick, that is ok. Then place bowl in the refrigerator for about 10 minutes.
Meanwhile it is time to crush the Oreos. You can put them in in the food processor and chop until they are crumbs, or you can place them in a zip top bag and crush with a mallet or rolling pin.
Remove the pudding mixture from the refrigerator and whip in the cool whip until well blended.
Place about ½ and inch of crushed Oreo at the bottom of each
cup. Spoon pudding mixture evenly into each cup until they are about 3/4 of the way full, top with a thick layer of crushed Oreos. Place in the refrigerator for 20 minutes.
Melt chocolate chips and shortening in a microwave safe bowl
or double boiler. Place in a piping bag and cut a small hole in the tip. Pipe the chocolate on to decorate Milano cookies like gravestones or ghosts.
Remove the pudding cups from the refrigerator and press the
bottom half a decorated Milano cookie into each cup. Add gummy worms and sprinkles to create a mini “graveyard”
Serve immediately.