Place the Oreos into a food processor, you will need to do this in batches. Process until they form crumbs. Place the crumbs into a large bowl and set aside.
Add the milk and chocolate pudding mix to a large bowl, and stir together for 2 minutes until it begins to thicken. Add the whipped topping and fold it in until there are no streaks.
Add ½ cup of the chocolate syrup and give it a few stirs. You want it to look streaky. Place it in the fridge until ready to assemble.
Lay out 18 9-ounce or similar-sized cups or serving containers. Place 2 tablespoons of the cookie crumbs in the bottom of the cups. Add just under ¼ cup of the pudding mix on top. Repeat with 2 more tablespoons of cookie crumbs and the remaining pudding.
Finally, add 1 tablespoon of the cookie crumbs on top of each cup.
Add the remaining ½ cup of chocolate syrup to the remaining cookie crumbs and stir it all together. This will be clumpy and moist looking. Set aside.
Decorate Milano cookies with black icing to say “RIP” or any saying you want, and add them to the cups. Add peep ghosts to the cups. I like to add the peeps and cookies to half of the cups, so they look different, but do as many as you want. Also, try and press them in gently into the pudding, so they stick up.
Take the clumpy cookie crumbs and add this to the tops of the cups to resemble freshly dug graves and uneven Earth. Add the mini pumpkin candies and Halloween sprinkles.
Chill until serving or serve immediately.
Notes
Nutritional value does not include garnishes.
Decorate these any way that you'd like.
These make 18 9 ounces cups, you can halve the cup size for younger children.
This can be made in a large bowl or a baking dish as well and scooped as needed.
I do not recommend freezing this recipe.
I find it easiest to decorate the cookies with a toothpick.