In a mixing bowl, combine the milk and instant chocolate pudding mix. Whisk until smooth and let it sit for 5 minutes to thicken.

In another bowl, beat the softened cream cheese and powdered sugar until smooth. Fold in the Cool Whip until well combined.

In a 9x9 inch baking dish, layer half of the crushed Oreos, followed by the pudding mixture, and then the cream cheese mixture. Repeat the layers, finishing with the remaining crushed Oreos on top.

Refrigerate the dirt cake for at least 2 hours before serving to allow it to set.