Coat an 8-inch square baking dish with non-stick spray. Set aside.
In a bowl, combine the crushed Oreos and melted butter. Press the mixture into the prepared dish. Cover and freeze for at least 30 minutes.
Mix the pudding mix and milk in a bowl. Whisk until smooth, cover, and refrigerate for 20 minutes to set.
Beat the cream cheese and powdered sugar together in another bowl until fluffy. Fold in the 1 cup of whipped topping and spread this over the frozen crust.
Layer the chocolate pudding mixture on top.
Spread the remaining whipped topping over the pudding layer. Sprinkle the top with crushed Oreo cookies.
Cover and refrigerate for at least 4 hours or freeze for 90 minutes before slicing to serve.