Step 1: Crush the entire package of Oreo cookies, including the cream filling, until fine crumbs are formed. A food processor works best, or place them in a large zip-top bag and crush with a rolling pin. Set aside 1 cup of the crumbs for the top layer.
Step 2: In a large mixing bowl, beat the softened cream cheese and softened butter with an electric mixer until light and fluffy, about 2-3 minutes. Ensure there are no lumps.
Step 3: Gradually add the powdered sugar to the cream cheese mixture, beating until well combined and smooth. Scrape down the sides of the bowl as needed to ensure everything is incorporated.
Step 4: In a separate large bowl, whisk together the cold milk and instant vanilla pudding mixes for 2-3 minutes, or until the mixture thickens. Let it stand for 1-2 minutes to fully set.
Step 5: Gently fold the thawed whipped topping into the pudding mixture until no streaks of whipped topping remain. Be careful not to overmix, which can deflate the whipped topping.
Step 6: Add the cream cheese mixture to the pudding and whipped topping mixture. Fold them together until just combined and smooth, creating your creamy filling.
Step 7: To assemble the dirt cake, choose a clear 9×13 inch baking dish, a trifle bowl, or individual serving cups. Start with a layer of the crushed Oreos at the bottom, then spread half of the creamy filling over the Oreo layer. Repeat with another layer of crushed Oreos, followed by the remaining creamy filling. Finish with a generous final layer of the reserved crushed Oreo crumbs.
Step 8: Cover the dish tightly with plastic wrap and refrigerate for at least 4 hours, or preferably overnight. This allows the cake to set and the flavors to meld beautifully.
Step 9: Just before serving, decorate your dirt cake with gummy worms for a classic “dirt patch” look. You can also add plastic flowers or a small clean shovel for extra fun.