Step 1: Prepare the cookie crumbs. Place the chocolate sandwich cookies into a large zip-top bag and crush them using a rolling pin or pulse them in a food processor until fine crumbs form. Set aside.
Step 2: Create the cream cheese layer. In a large mixing bowl, beat the softened butter and softened cream cheese together with an electric mixer until light and fluffy. This should take about 2-3 minutes.
Step 3: Add the sweetness. Gradually beat in the powdered sugar until fully incorporated and smooth.
Step 4: Incorporate milk and whipped topping. Beat in 1/2 cup of milk until smooth. Gently fold in the thawed whipped topping until no streaks remain. Set this mixture aside.
Step 5: Prepare the pudding. In a separate large bowl, whisk together the two packages of instant vanilla pudding mix with 3 cups of cold milk for about 2 minutes, or until the pudding starts to thicken. Let it sit for 5 minutes to set completely.
Step 6: Combine the cream layers. Gently fold the prepared pudding into the cream cheese mixture until well combined. Be careful not to overmix, as this can deflate the whipped topping.
Step 7: Assemble the Dirt Cake Dessert Cups. Get your serving cups ready (clear cups work best to show off the layers!). Start with a layer of cookie crumbs at the bottom, about 1-2 tablespoons depending on cup size.
Step 8: Add the creamy filling. Spoon or pipe a generous layer of the cream/pudding mixture over the cookie crumbs.
Step 9: Repeat the layers. Continue layering crumbs and cream mixture, ending with a layer of cookie crumbs on top, just like freshly dug "dirt."
Step 10: Chill for best results. Cover the Dirt Cake Dessert Cups and refrigerate for at least 1-2 hours to allow the layers to set and flavors to meld. For best results, chill overnight.
Step 11: Decorate and serve. Before serving, you can decorate with gummy worms, chocolate rocks, or a sprig of fresh mint to enhance the "dirt" theme. Enjoy your delightful Dirt Cake Dessert Cups!