Set out the Oreo crumb pie shell so it is ready to be filled.
Beat the cream cheese and powdered sugar together and fold in about 1/2 cup of Cool Whip. Stir in the Oreo chunks. Spread everything in the bottom of the crust.
Using the same bowl or a new one, whisk together the pudding mix and chocolate milk. Fold in 1 cup of Cool Whip. Spread this as your second layer.
Top off the pie with the remaining Cool Whip. Add mini Oreos around the edge or even crumble some for the top, if you wish. If you have squirt bottles of chocolate or dulce de leche, add some swirls or cross-hatching to the top.
Chill pie at least two hours before serving. Keep refrigerated thereafter.
OM NOM NOM!