In a mixing bowl, crush 33 Oreo cookies until they're fine crumbs using a food processor or rolling pin in a plastic bag.
Add the melted butter to the Oreo crumbs and mix until combined.
Press this mixture into the bottom of a 9x13-inch baking dish to form an even crust.
In a separate mixing bowl, beat the cream cheese until smooth.
Gradually add 1/4 cup powdered sugar to the cream cheese and mix until fully combined.
In another bowl, whip 16 oz heavy whipping cream with 2 teaspoons vanilla extract and 1/2 cup powdered sugar until stiff peaks form.
Fold the whipped cream into the cream cheese mixture until smooth and creamy.
Spread the cream cheese layer evenly over the Oreo crust.
In a large bowl, whisk together the instant vanilla pudding mix and 2 cups of cold milk until thickened.
In another bowl, whisk together the instant chocolate pudding mix and remaining 2 cups cold milk until thickened.
Spread the vanilla pudding mixture over the cream cheese layer.
Spread the chocolate pudding mixture over the vanilla pudding layer, smoothing each layer with a spatula.
Spread the remaining 1 cup homemade whipped cream over the chocolate pudding layer and smooth out.
Crush the reserved handful of Oreo cookies and sprinkle over the top for decoration.
Cover the dish with plastic wrap and refrigerate for at least 4 hours or preferably overnight to set layers and meld flavors.