In a large mixing bowl, whisk together the instant chocolate pudding mix with the cold milk until smooth and thickened, about 2-3 minutes.
Gently fold the whipped topping into the prepared pudding until evenly combined, creating a smooth, creamy mixture.
Spread a layer of crushed cookies at the bottom of your serving dish to mimic dirt.
Pour half of the chocolate pudding mixture over the crushed cookies, smoothing it out with a spatula for an even layer.
Add another layer of crushed cookies on top of the pudding layer to build up the 'dirt' effect.
Pour the remaining pudding mixture over the second cookie layer, smoothing the top gently.
Sprinkle the top with additional cookie crumbs for extra texture and 'dirt' appearance.
Decorate the top with gummy worms, placing some so they appear to wiggle out of the 'dirt' for a spooky effect.
Refrigerate the dirt cake for at least 2 hours to allow flavors to meld and the texture to set.
Once chilled and set, serve the dirt cake in slices or scoops, reveling in its playful, messy look and layered textures.
