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Crush the whole package of cookies in a food processor or in a large ziplock bag with a rolling pin. Reserve about 1 cup for topping.
Mix remaining crumbs with melted butter until fully combined. Press into the bottom of a 9×13-inch pan for the crust.
In a large bowl, beat softened cream cheese, powdered sugar, and half of the Cool Whip until smooth. Spread over the Oreo crust. Chill while you make the pudding.
In another bowl, whisk together chocolate pudding mix and cold milk for 2 minutes until it thickens. Spread over the cream cheese layer. Let sit for 10 minutes.
Spread remaining Cool Whip over the pudding layer. Sprinkle reserved Oreo crumbs on top.
Refrigerate at least 4 hours before serving. For cleaner slices, freeze for 30 minutes before cutting.
Serve chilled and enjoy!