Step 1: Place the chocolate sandwich cookies into a large gallon-sized resealable bag. Use a rolling pin to crush them into fine crumbs, leaving a few small chunks for texture.
Step 2: In a large mixing bowl, whisk together the instant chocolate pudding mix and the cold milk for about 2 minutes until well combined. Let it stand for 5 minutes to thicken.
Step 3: Gently fold the thawed whipped topping into the thickened pudding until no white streaks remain and the mixture is light and fluffy.
Step 4: Prepare 6 to 8 individual clear cups. Spoon about 2 tablespoons of cookie crumbs into the bottom of each cup.
Step 5: Follow with a layer of the pudding mixture, then another layer of cookie crumbs. Repeat until the cups are nearly full, ending with a layer of cookie crumbs on top.
Step 6: Push two or three gummy worms into the top layer of each cup so they appear to be crawling out of the “dirt.”
Step 7: Refrigerate the cups for at least 1 hour before serving to allow the layers to set and the cookies to soften slightly.