Place all Oreo cookies in a large zip-top bag.
Seal the bag securely and place it on a flat counter surface.
Using a rolling pin, crush the cookies into small chunks and crumbs. The cookies should remain slightly chunky and should not be crushed into fine crumbs.
Reserve approximately 1/3 of the crushed Oreo cookies for the topping.
Transfer the remaining crushed Oreo cookies to a 9x13-inch baking pan.
Pour the melted butter over the crushed cookies.
Stir until the cookie crumbs and butter are evenly combined.
Press the Oreo mixture firmly and evenly into the bottom of the pan to form a crust.
In a separate mixing bowl, combine the instant chocolate pudding mixes and cold milk.
Whisk until smooth and slightly thickened.
Cover the pudding mixture and refrigerate until set.
In a medium mixing bowl, beat the softened cream cheese until smooth.
Gradually add the powdered sugar.
Continue mixing until the cream cheese and powdered sugar are fully combined and smooth.
Gently fold in one container of thawed Cool Whip until evenly incorporated.
Spread the cream cheese mixture evenly over the prepared Oreo crust.
Remove the chilled chocolate pudding from the refrigerator.
Spread the chocolate pudding evenly over the cream cheese layer.
Spread the second container of thawed Cool Whip evenly over the chocolate pudding layer.
Sprinkle the reserved Oreo crumbs evenly over the top.
Cover the pan with plastic wrap or foil.
Refrigerate for at least 2 hours before serving to allow the layers to set.
Slice into squares.
Serve chilled.