Crush the cookies: Start by placing the entire package of chocolate sandwich cookies (15.35 ounces) in a zip-lock bag and crush them into fine crumbs using a rolling pin or your hands. This will create the "dirt" base for your dessert.
Make the cream cheese mixture: In a mixing bowl, beat together 1 package of softened cream cheese (8 ounces) and 1 cup of powdered sugar until smooth and creamy. Make sure there are no lumps for the best texture.
Prepare the pudding: In another bowl, whisk together 2 cups of milk and 1 package of instant chocolate pudding mix (3.9 ounces) until the mixture thickens, about 2 minutes. You'll want a thick, creamy consistency.
Combine mixtures: Gently fold the pudding mixture into the cream cheese mixture until well combined, ensuring a smooth consistency.
Add whipped topping: Carefully fold in 1 container of thawed whipped topping (8 ounces) into the combined pudding and cream cheese mixture until fully incorporated and fluffy.
Layer the dessert: In a serving dish, starting with the cookie crumbs, layer the cookie mixture and the pudding mixture, alternating between the two. End with a final layer of cookie crumbs on top.
Decorate: For added fun, sprinkle extra cookie crumbs on top and arrange gummy worms on the surface or around the dish creatively.
Chill: Cover the dessert and chill in the refrigerator for at least 2 hours before serving. This allows the flavors to meld and the dessert to set.