Place the chocolate sandwich cookies into a food processor and pulse until they reach a fine, dirt-like consistency. If using a plastic bag, seal it tightly and crush the cookies thoroughly with a rolling pin.
In a medium mixing bowl, whisk together the cold milk and the instant chocolate pudding mix for about 2 minutes until the mixture begins to thicken.
Gently fold the thawed whipped topping into the pudding mixture using a rubber spatula until the color is uniform and no streaks remain.
Spoon a layer of the chocolate mixture into the bottom of each of the four clear cups.
Add a generous layer of the crushed cookie crumbs over the pudding.
Repeat the layers until the cups are filled, finishing with a final layer of cookie crumbs on top to resemble garden soil.
Shape your orange candies into small carrot shapes and press them slightly into the top layer of cookie crumbs.
Tuck a small sprig of fresh mint or parsley into the top of each candy carrot to act as the leafy greens.
Chill the cups in the refrigerator for at least 30 minutes before serving to ensure the pudding sets firmly.