Pour the milk into a mixing bowl and whisk in the chocolate pudding mix until well combined and smooth, then let it sit for a few minutes to thicken slightly.
If using, whip the heavy cream in a separate bowl until soft peaks form, then gently fold it into the pudding mixture for extra creaminess.
Distribute the pudding evenly into individual cups or small jars, filling each about halfway to leave room for layering.
Sprinkle a generous layer of crushed cookies over the pudding, mimicking dirt and creating a crumbly, textured surface.
Add miniature tombstone decorations or candies on top of the 'dirt' to create haunting grave markers.
If desired, dust the finished cups with edible glitter or shimmer for a spooky, sparkly effect.
Chill the pudding cups in the refrigerator for at least 30 minutes to set and allow flavors to meld.
Once chilled and set, serve the Graveyard Pudding Cups with a spooky flourish and enjoy the layered textures and creepy visual appeal.