Begin by placing a layer of cookies in a greased 9 x 13 casserole dish.
Next take a large mixing bowl and whip together the cream cheese + powdered sugar until completely combined. Then mix in ½ cup coarsely chopped Oreos and fold in 1 ½ cups whipped topping.
Add in the softened cream cheese mixture in spoonfuls over the cookies and press into an even layer.
In a separate mixing bowl combine the pudding mix and milk for 5 minutes or until the mixture has thickened.
Spread the pudding mixture over the cream cheese layer. Top with a layer of the remaining whipped topping.
After that place the remaining cookies in a ziploc bag and crush. Sprinkle the crushed cookies over the whipped topping layer. Cover and place the dessert in the refrigerator to set for at least 8 hours.
Finally drizzle chocolate over the top of the dessert when ready to serve.