1. Place all but 6 cookies in a food processor; pulse into fine crumbs. Measure out 2 cups of crumbs, transfer to a bowl, and reserve the remaining crumbs and whole cookies for later.
2. Add confectioners’ sugar and melted butter; stir to combine. Transfer to a parchmentlined 13x9inch baking dish.
3. In a stand mixer, beat cream cheese, 1 cup cookie butter, and confectioners’ sugar until smooth. Fold in 1½ cups whipped topping. Spread over the crust.
4. Beat pudding mix, cream, and milk in a large bowl until smooth (2–3 minutes). Spread evenly over the cream cheese layer.
5. Top with the remaining 3 cups whipped topping. Warm the remaining ¼ cup cookie butter in the microwave for 30 seconds until pourable. Drizzle over the whipped topping and swirl with a sharp knife.
6. Cover and refrigerate for at least 4 hours. Decorate with reserved cookie crumbs and whole cookies. Cut into squares and serve chilled.