Prepare the Pudding: Add the instant chocolate pudding mix and cold milk to a medium bowl. Whisk for about 2 minutes, or until the mixture begins to thicken. Refrigerate for 10 minutes.
1 package instant chocolate pudding mix, 2 cups cold milk
Fold In the Whipped Topping: Gently fold the thawed whipped topping into the chilled pudding until no white streaks remain. Refrigerate the mixture for another 20 minutes.
16 ounces frozen whipped topping
Crush the Oreos: While the pudding mixture chills, place the Oreo cookies in a food processor or blender. Pulse until they form fine crumbs. You can also place them in a sealed plastic bag and crush them with a rolling pin.
12 Oreo cookies
Make the Tombstones: Use the black decorating icing to write “RIP” on each Milano cookie. Allow the icing to set for a few minutes.
1 tube black decorating icing, 12 Milano cookies
Add the First Layer: Divide about half of the pudding mixture among the 12 clear cups.
Add the Oreo Dirt: Sprinkle about half of the crushed Oreo cookies evenly over the pudding.
Repeat the Layers: Divide the remaining pudding mixture among the cups, then finish each one with the remaining Oreo crumbs.
Decorate the Cups: Press one decorated Milano cookie into each cup to resemble a tombstone. Add gummy worms and candy pumpkins as desired.
Gummy worms, Candy pumpkins
Chill and Serve: Keep the dirt cups refrigerated until ready to serve. For the best texture, add the Milano tombstones and candy decorations shortly before serving.
Storage: Cover the undecorated cups and refrigerate them for up to 3 days. Once decorated, the cups can still be refrigerated, but the Milano cookies will gradually soften.