Crush 12 Oreo cookies into fine crumbs and set aside.
In a bowl, mix the chocolate pudding mix with milk and whisk until smooth.
In another bowl, whip the heavy cream with powdered sugar until stiff peaks form.
Gently fold the whipped cream into the chocolate pudding mixture.
In a rectangular dish, layer half of the crushed Oreo cookies at the bottom.
Spread half of the chocolate pudding mixture over the cookies.
Add another layer of whole Oreo cookies on top of the pudding.
Pour the remaining pudding mixture over the cookies.
Top with the remaining crushed Oreo cookies.
Chill in the refrigerator for at least 2 hours before serving.