Crush the Oreos. Place Oreos into the ziplock bag. Use a rolling pin or large can to crush them into small pieces. Set aside.
Mix the ingredients. To a large bowl, add Greek yogurt, milk, and dry pudding mix. Whisk until thickened, about 2 minutes. Add whipped topping and fold into the pudding mix.
Layer the dirt cups. Add about 2 tablespoons of crushed Oreos to the bottom of each cup. Using a small ice cream scoop, place 1-2 scoops of the pudding mixture on top of the Oreos. Repeat, sprinkling the leftover Oreos on top of the pudding.
Garnish. Garnish with strawberries, raspberries, or blueberries. Refrigerate until serving.
Make Ahead - we recommend making this recipe on the day you plan to serve to prevent the sandwich cookies from getting soggy. The pudding mixture can be prepped up to 3 days before then layered with the crumbled Oreos on the day of the event. Storage - tightly cover each cup with plastic wrap and store in the refrigerator until ready to serve.