Prepare the chocolate pudding by whisking the pudding mix with milk until smooth and slightly thickened, about 2-3 minutes. Pour the prepared pudding into a bowl and set aside.
In a separate bowl, whip the heavy cream (and sugar if using) until soft peaks form, creating a fluffy whipped topping.
Gently fold the whipped cream into the prepared pudding to create a creamy, layered mixture.
Spoon a layer of the pudding mixture into the bottom of each serving cup or small jar, smoothing the surface with the back of a spoon.
Sprinkle a generous layer of crushed cookies over the pudding to resemble dark soil, creating a textured, earthy surface.
Repeat layering with another spoonful of pudding and a sprinkle of crushed cookies to build a mini graveyard scene.
Decorate the top with edible gravestone decorations, inserting small fondant stones or placing pre-made gravestones into the pudding layers.
Add spooky edible details, such as tiny candy spiders or web decorations, to enhance the eerie effect.
Optional: Chill the assembled desserts in the refrigerator for at least 10 minutes to set the layers and meld the flavors.
Serve immediately or refrigerate until ready to enjoy, revealing a spooky miniature landscape of chocolate, cookies, and festive decorations.
