2 tbsp butter, very softened
1 brick (8-oz) cream cheese, softened
1/2 cup creamy peanut butter
1 1/2 cups powdered sugar, divided
1 large carton (16-oz) frozen whipped topping, thawed, divided
21 miniature peanut butter cups, divided
1 cup cold milk
1 box (3.9-oz) instant chocolate pudding mix
Crush 16 of the cookies; mix with the butter and press onto the bottom of a 9-inch square baking dish.
In large mixer bowl, beat the cream cheese, peanut butter, and powdered sugar until smooth. Fold in half the whipped topping and spread over the Oreo crust.
Chop 15 of the peanut butter cups and sprinkle over the cream cheese mixture.
In another large bowl, beat the milk, pudding mix, and remaining half cup of powdered sugar on low speed for 2 minutes; let stand for 2 minutes to soft set. Fold in the remaining half of the whipped topping. Spread pudding mixture over the peanut butter cups.
Crush the remaining four cookies and sprinkle over top of the dessert
Cut the remaining peanut butter cups in half and sprinkle over the crushed cookies.
Cover dish and chill for at least 3 hours before cutting into 12 squares to serve.