Make the Pudding & Crush Oreos: Whisk the milk and instant pudding mix together in a large bowl, set aside to thicken & set. Add oreo package to food processor & pulse until oreos are all crushed into a coarse crumb (I like some varying chunks). You can also place oreos in a large ziplock bag and seal. Use a rolling pin to crush oreos.
Make the Whipped Cream (see notes if using cool whip): In a large bowl with hand mixer or stand mixer with whisk attachment, whip whipped cream until soft peaks. Fold in vanilla extract. Remove from bowl & set aside. No need to clean out bowl for the next step.
Whip Cream Cheese & Finish Pudding: In bowl of the stand mixer, beat cream cheese until creamy and soft. Add powdered sugar and beat until smooth. Add set vanilla pudding to cream cheese and beat again on medium until combined scrape the bottom and sides of the bowl & make sure everything is incorporated. Next, fold in whipped vanilla cream with rubber spatula. Set aside in the fridge.
Assemble Dirt: Use any dish: an 8 or 9inch circle dish, 9x13 dish, trifle dish or smaller mugs. Add one layer of oreos to the bottom of the dish, then filling, and oreos again until it is filled to the top. Cover the top with the rest of the oreos.