
Crush 16 cookies and toss them with the butter. Press this mixture into an ungreased 9-inch square dish, then set it aside.
In a large bowl or stand mixer, beat the cream cheese, peanut butter and 1 cup of confectioners' sugar until smooth. Fold in half the whipped topping. Spread this mixture over the crust, then sprinkle the chopped peanut butter cups over the top.
In another large bowl (or a clean stand mixer bowl), beat the milk, pudding mix and remaining 1/2 cup confectioners' sugar on low speed for two minutes. Let it stand for two minutes, or until soft-set, then fold in the remaining whipped topping. Spread the cream topping over the peanut butter cups.
Crush the remaining cookies, and sprinkle them over the top. Cover and chill for at least three hours before serving.