Add the 2 packages of chocolate instant pudding and 4 cups of milk to a large bowl. Mix with an electric mixer starting on low speed and switching to medium speed until it becomes a thick pudding consistency and thoroughly combined (about 2-3 minutes).
In a medium bowl, add 1 cup of thawed cool whip and 1 cup of the chocolate pudding from step 1. Mix on medium speed until combined about 2 minutes.
Place pudding and whipped topping mixture in the refrigerator while you prepare the “dirt”.
Place Oreos in the base of a food processor and pulse until medium fine crumbs are created. If you do not have a food processor, you can crush the Oreos by placing them in a zip top bag and rolling over them with a rolling pin until completely crushed into crumbs.
Create your work station for assembly. Remove the pudding and whipped topping mixture from the refrigerator. Lay out the plastic cups. You can either work on all cups simultaneously or 1 by 1.
Start by layering 1 tablespoon of the Oreo dirt in the bottom of the cup.
Next, layer with 1⁄2 cup of chocolate pudding. Tap the cup on the counter to level the pudding for the next layer.
Add another tablespoon of dirt over the chocolate pudding.
Next, add a heaping 1⁄4 cup of the whipped topping mixture over the dirt. Tap the cup on the counter to level out the layer.
Finish with a last tablespoon of dirt and garnish with gummy worms and candy of your choice! Allow the dirt cups to chill for at least 30 minutes before serving and enjoy.
This recipe makes 8 large servings. You use smaller cups and divide the ingredients to make smaller servings or cut the recipe in half to just make 4.
Be careful when adding the pudding and whipped topping mixture to the cup. Be sure that you are keeping the sides of your cup clean so you can see the layers. If you make a mistake and pudding or whipped topping smudges end up on the cup, take a wet paper towel and clean it before proceeding to the next step.
You can make chocolate toppings using candy melts or melted white chocolate using silicone molds for really unique decorating or simply stick to candy eyeballs and gummy worms.
If you prefer not to use cool whip you can skip it and just layer the pudding and dirt.
The pudding can be made ahead for these dirt cups and then everything can be layered before serving.
Oreos and gummies become soggy in the refrigerator so these cups are best served the day they are made but can be stored in the refrigerator for 3 days if there are leftovers.