Step 1: Crush the Oreo cookies. Place 36 Oreo cookies (including the cream filling) into a food processor and pulse until they resemble fine, moist dirt. Alternatively, place them in a large zip-top bag and crush with a rolling pin until finely crumbled. Set aside about 1 cup of the crushed cookies for topping.
Step 2: In a large mixing bowl, beat the softened cream cheese with the powdered sugar until smooth and creamy.
Step 3: In a separate medium bowl, whisk together the cold milk and instant vanilla pudding mix for about 2 minutes until it begins to thicken. Let it sit for 2-3 minutes to set completely.
Step 4: Gently fold the prepared pudding into the cream cheese mixture until well combined.
Step 5: Fold in the whipped topping until no streaks remain and the mixture is light and fluffy.
Step 6: Begin layering. Place about 1-2 tablespoons of crushed Oreos at the bottom of each individual serving cup.
Step 7: Spoon or pipe a generous amount of the creamy pudding mixture over the Oreo layer.
Step 8: Repeat the layers: add another layer of crushed Oreos, followed by another layer of the creamy mixture. Continue until your cups are nearly full, ending with a layer of the creamy mixture.
Step 9: Top each cup generously with the reserved crushed Oreo ‘dirt.’
Step 10: For the classic look, add a few gummy worms or other fun candy decorations peeking out of the ‘dirt.’
Step 11: Chill the Dirt Cake Dessert Cups in the refrigerator for at least 1-2 hours before serving. This allows the layers to set and the flavors to meld beautifully.