1. Prepare the Brownie Crumbles: If using a fresh batch of brownies, ensure they are completely cooled. Once cool, crumble the brownies into small, irregular pieces. You want them to resemble loose soil, so don’t be afraid to break them down with your hands or a fork. Set aside about half a cup of the crumbles for later.

2. Make the Chocolate Pudding: In a large mixing bowl, whisk together the instant chocolate pudding mix and cold milk for about 2 minutes, or until the mixture begins to thicken. It will still be a bit loose, but it should be noticeably thicker than milk.

3. Fold in Whipped Topping: Gently fold the thawed whipped topping into the prepared chocolate pudding. Mix until just combined and no streaks of white whipped topping remain. Be careful not to overmix, as this can deflate the whipped topping and make the pudding less airy.

4. Crush the Oreo Cookies: Place the Oreo cookies in a large zip-top bag and crush them finely using a rolling pin, or pulse them in a food processor until they resemble fine dirt. You want a consistent, sandy texture.

5. Assemble the Cups: Begin by placing a layer of about 2 tablespoons of crumbled brownies at the bottom of each clear plastic cup or glass jar. This forms the first “dirt” layer.

6. Add Pudding and Oreo Layers: Spoon about 1/4 to 1/3 cup of the chocolate pudding mixture over the brownie layer in each cup. Then, sprinkle a generous layer of the crushed Oreo cookies over the pudding. Repeat these layers (brownie, pudding, Oreo) until the cups are nearly full, ending with a final layer of crushed Oreos on top to create the “graveyard dirt” effect.

7. Chill and Decorate: Place the assembled dirt cups in the refrigerator for at least 30 minutes to allow the pudding to set and the flavors to meld. While they chill, prepare your gravestones by writing “RIP” or other spooky messages on the Milano cookies with black icing gel or an edible marker. Once chilled, insert a Milano cookie gravestone into the top of each cup. Arrange gummy worms so they look like they are crawling out of the “dirt,” and add any other Halloween candies like candy pumpkins or candy corn for extra festive flair.