PREP PAN: Lightly spray a 9 x 13-inch baking dish with nonstick spray.
MAKE CRUST: Place the Oreo cookies in a food processor and pulse until fine crumbs form. Reserve ¼ cup crumbs for topping.
PRESS CRUST: In a bowl, mix the remaining Oreo crumbs with 6 tablespoons melted butter. Press firmly into the bottom of the baking dish. Refrigerate while preparing the next layer.
MAKE CREAM CHEESE LAYER: In a mixing bowl, beat the softened cream cheese until smooth. Add ¼ cup granulated sugar and 2 tablespoons milk and beat until creamy. Set aside.
MAKE WHIPPED CREAM: In a large bowl, combine 1 cup heavy whipping cream, ¼ cup plus 2 tablespoons powdered sugar, 2 tablespoons French vanilla pudding mix, and 1 teaspoon vanilla extract. Beat with an electric mixer until stiff peaks form.
COMBINE LAYER: Fold half of the whipped cream mixture into the cream cheese mixture until smooth. Spread evenly over the Oreo crust. Refrigerate for 10 minutes.
MAKE PUDDING: In a bowl, whisk together 2 boxes chocolate pudding mix and 3 cups milk until smooth. Let stand 5 minutes until slightly thickened.
ADD PUDDING LAYER: Spread the chocolate pudding evenly over the cream cheese layer.
TOP WITH WHIPPED CREAM: Spread the remaining whipped cream over the pudding layer.
GARNISH: Sprinkle the reserved Oreo crumbs over the top and add chocolate shavings.
CHILL: Cover and refrigerate for at least 4 hours until fully set.
SERVE: Slice into 12 pieces. Top each slice with whipped cream and a mini Oreo before serving.
Notes
Make-Ahead: This dessert is perfect for making a day ahead. The layers hold together even better after chilling overnight.Cool Whip Shortcut: You can substitute two 8-ounce containers whipped topping for the homemade whipped cream.Freezer Shortcut: If you need to speed up the chilling process, place the dessert in the freezer for about 1 hour, then transfer to the refrigerator until ready to serve.Chocolate Curls: Use a vegetable peeler to shave curls from a chocolate bar for easy garnish.Storage: Store covered in the refrigerator for up to 4 days.