1. Place chocolate cookies into a large sealable plastic bag and crush into fine crumbs. Sprinkle half of the crumbs into the bottom of a 9x13-inch baking dish.
2. In a large bowl, whisk together pudding mix, cream cheese, milk, powdered sugar, and whipped topping; spread evenly over the cookies in the dish. Top with remaining cookie crumbs. Cover and refrigerate for at least 2 hours.
3. Using the oblong cookies for gravestones, get creative and use the icing pen to write messages on the top half of each cookie. Stick the cookies upright into the "dirt" pudding. Top with other fun toppings as desired.