Step 1: Make the Pudding & Crush Oreos - Whisk together milk and instant pudding mix in a large bowl, allowing it to thicken while you prepare your cookies. Crush the oreo package using a food processor until they reach a coarse crumb consistency; alternatively, place them in a ziplock bag and crush them with a rolling pin.
Step 2: Make the Whipped Cream - In another bowl, use a hand mixer or stand mixer with a whisk attachment to whip heavy cream until soft peaks form, then gently fold in vanilla extract for added flavor.
Step 3: Whip Cream Cheese & Finish Pudding - Beat softened cream cheese until creamy and smooth before adding powdered sugar gradually until well-combined. Mix in the set pudding until everything is blended nicely before folding in your whipped cream carefully using a rubber spatula.
Step 4: Assemble Dirt - Choose your favorite dish and start layering by placing crushed oreos at the bottom followed by filling made from cream cheese and pudding mixture, then more oreos on top until filled to your desired height, finishing off with additional oreo crumbs on top.