Using a food processor, process 30 Oreo cookies until they are a fine crumb. (It's okay if there are a few cookie chunks.) Set aside 0.25 cup crumbs for the topping.

In a large bowl, combine remaining cookie crumbs with melted butter until fully incorporated.

Press cookie mixture into an ungreased 9-inch square dish; set aside.

In a large bowl, beat the cream cheese with a hand mixer until light and fluffy.

Add peanut butter and 1 cup of confectioners' sugar. Stir together until smooth.

Fold in the whipped topping. Spread over crust.

Sprinkle with chopped peanut butter cups.

In another large bowl, beat the milk, pudding mix, and confectioners' sugar until it begins to thicken (about 2 minutes).

Fold in whipped topping and continue folding until fully combined. Spread over the chopped peanut butter cups.

Sprinkle the reserved cookie crumbs over the top. Cover and chill for at least 2 hours.