Use a food processor (or a zip top bag and a rolling pin) to crush the Oreos into fine crumbs.
Into a medium bowl, pour in the cookie crumbs and melted butter. Stir until thoroughly mixed.
Pour into a 9 x 13 baking dish and use a spatula (or the bottom of a measuring cup) to evenly press the crumbs across the dish.
In the same medium bowl, add the cream cheese and beat with a hand mixer until fluffy. Add in the 2 Tablespoons of milk and sugar and mix well.
Fold the contents of one of the 8 oz Cool Whip containers into the cream cheese mixture.
Spread the cream cheese mixture over the cookie crust and pop it into the fridge to set for about 10 minutes.
While it's setting, to a large bowl, add the pudding mixes and 2 3/4 cups milk and beat on medium until it starts to thicken.
Spread the pudding mixture over the cream cheese layer. Put back into the fridge to set for another 10 minutes.
Once set, gently spread the remaining 8 oz of Cool Whip over the top and sprinkle with mini chocolate chips.
Cover with plastic wrap and let chill for at least 4 hours in the fridge or 1 hour in the freezer before you slice.
Do not remove the cream centers from the cookies. Use regular Oreos, not Double Stuff. 36 cookies = 3 cups of crumbs.
Use 2 boxes of instant pudding, do not use Cook n Serve.
For a fancier presentation, substitute shaved chocolate for the chocolate chips. Use a vegetable peeler to shave a bar of bittersweet chocolate, creating short or long ribbons to sprinkle on top. There's less sugar in a bittersweet bar, it simply shaves better creating prettier chocolate shavings.
If you have extra time, I highly recommend popping the dessert into the freezer after each step. It makes it easier to spread each layer.
If you prefer, you can use an equal amount of homemade whipped topping instead of Cool Whip. To substitute whisk 3 cups of heavy whipping cream until medium peaks form.
You can make this dessert up to 3 days ahead, keep refrigerated.