Set aside 4 Oreos, then separate the remaining Oreos into two cookies. Place a single layer of cookies in the bottom of an 8x8 baking dish.
Prepare the pudding by whisking together the pudding mix and milk until well combined.
Use half the pudding to cover the cookies, then top with another layer of Oreos.
Add half the whipped topping to the pudding and whisk to combine.
Spread the pudding and whipped topping mixture over the top of the cookies, then add another layer of Oreos.
Spread the remaining whipped topping over the top of the dessert, then place in the refrigerator to chill for at least 4 hours. When ready to serve, crush the remaining Oreos and sprinkle over the top of the dessert.