Step 1: Place the chocolate sandwich cookies in a large zip-top bag and crush them with a rolling pin until they resemble coarse dirt. Set aside about 1/3 of the crumbs for the top layer.
Step 2: In a large bowl, cream together the softened cream cheese, butter, and powdered sugar until smooth and fluffy.
Step 3: In a separate bowl, whisk together the cold milk and instant chocolate pudding mixes for 2 minutes until thickened. Let it sit for 5 minutes.
Step 4: Gently fold the whipped topping into the cream cheese mixture, then fold in the prepared chocolate pudding until well combined.
Step 5: In a large serving bowl or individual cups, layer the cookie crumbs followed by the pudding mixture. Repeat the layers, ending with a thick layer of cookie crumbs on top.
Step 6: Press gummy worms into the top ‘dirt’ layer so they look like they are crawling out. Refrigerate for at least 1 hour before serving.