Pour the cold milk into a mixing bowl and add the instant chocolate pudding mix. Whisk for two minutes until the mixture thickens.
Let the pudding stand for five minutes so it sets fully.
Spoon a layer of pudding into each clear cup, filling them about halfway.
Add a layer of crushed chocolate sandwich cookies on top of the pudding in each cup to create the dirt effect.
Spoon the remaining pudding over the cookie layer in each cup.
Top each cup with another sprinkle of crushed cookies.
Use the black decorating icing to write short words like "RIP" on each rectangular chocolate cookie. Stand one cookie upright in the center of each cup as a tombstone.