Place the whole dark circular chocolate sandwich cookies into a gallon-size freezer bag. Seal it tightly while leaving a tiny air gap. Crush them firmly with a rolling pin using a heavy rocking motion until they break down into small irregular pieces. (I tried using a food processor the first time but it turned everything into dust, you want some crunchy pebbles left.) You'll see a mix of fine dark brown crumbs and small chunky cookie bits. The filling should grease the crumbs slightly so they clump naturally. Continue until no large whole halves remain. Do not over-crush the cookies into powder because a texturized crunch keeps the dessert from becoming mushy. Crush the pieces unevenly, the variety in size mimics real soil.

Pour the dry dark brown instant chocolate pudding powder into the bottom of the container. Measure exactly two cups of cold whole milk and pour it over the powder. Whisk vigorously using a rapid circular motion making sure to scrape the bottom crevices where dry pockets hide. Whisk continuously for exactly 120 seconds until the liquid begins to resist the wires. The pale white liquid will rapidly darken into a glossy chocolate brown color. You will hear the splashing sound quiet down as the mixture thickens into a heavy cream texture. Let it rest on the counter at a room temperature of 68°F for 5 minutes. Miss this resting window and the cornstarch will not hydrate properly which leads to a runny base. Rest for 5 minutes, this allows the starch to set into a firm structure.

Spoon the fluffy white thawed whipped topping directly into the center of the set chocolate pudding. Use a rubber spatula to cut down through the middle then sweep around the edge in a gentle J-shaped motion. Rotate the bowl 45 degrees after each stroke to ensure even integration. Continue folding for about 2 minutes until the white streaks disappear into the brown mix. The deep brown pudding transforms into a lighter milk-chocolate tan shade. The texture becomes airy and mousse-like while remaining thick enough to hold its shape on a spoon. Do not stir roughly or you will deflate the incorporated air. Stop folding as soon as the color is uniform so the mixture retains its light volume. Fold gently with a spatula, keeping the air bubbles intact prevents a dense heavy cream layer.

Line up four clear plastic cups on a flat surface. Spoon two tablespoons of the crushed cookie pieces into the bottom of each cup to form an even dark layer. Drop three tablespoons of the light tan chocolate cream mixture directly over the crumbs. Repeat this alternating pattern until you reach the top rim finishing with a generous layer of dark cookies. Clear horizontal stripes of dark brown and light tan become visible through the plastic sides. The cookie crumbs sink slightly into the cream layers creating an uneven natural boundary line. The top layer should look completely dark and powdery like fresh garden soil. Pack the crumb layers loosely so the cream does not squish up the sides prematurely. Spoon the layers carefully, maintaining distinct bands ensures the classic dirt cup appearance.

Press two multi-colored gummy worms into the top cookie crumb layer of each cup. Push one end of each worm slightly down into the cream so it looks like it is tunneling. Arrange the exposed tails to drape loosely over the plastic rim. Place the finished cups into a refrigerator chilled to 38°F for exactly 60 minutes before serving to guests. The bright neon pink green and yellow colors of the worms contrast sharply against the dark brown soil background. The cookie crumbs absorb minimal moisture and lose their dry dustiness while the cream firms up. (I found that adding the worms before chilling helps them stay securely anchored in place.) Skip the refrigeration step and the layers will slide around when you dip a spoon inside. Chill for 60 minutes, cold temperatures set the fats so the dessert keeps its shape.