In a food processor, crush 16 Oreo cookies with 2 tbsp of butter. Press the crumbly mixture into a 9-inch baking dish and set aside.

In a stand mixer, whisk together the cream cheese, peanut butter, and one cup of powdered sugar until smooth. Fold in half of the whipped topping. Pour over the Oreo crust.

Coarsely chop the miniature peanut butter cups and pour three-fourths of the mixture over the peanut butter layer.

In a large mixing bowl, vigorously whisk the instant chocolate pudding, remaining powdered sugar, and milk for two minutes. Let the mixture sit for an additional two minutes to set up, then fold in the remaining whipped topping. Pour over the layered dessert.

Sprinkle the remaining crushed Oreo cookies and peanut butter cups. Chill for at least three hours before serving.