Crush the chocolate cookies into fine crumbs using a resealable bag and rolling pin or a food processor until they resemble soil. Set aside.
In a mixing bowl, beat the softened cream cheese with powdered sugar until smooth and creamy, about 2-3 minutes.
Gently fold the whipped cream into the cream cheese mixture, creating a light, fluffy filling.
Spoon a layer of cookie crumbs into the bottom of each serving cup, pressing slightly to form a base layer that mimics soil.
Top the cookie crumbs with a generous dollop of the creamy filling, spreading evenly with a spatula.
Insert gummy worms on top of the creamy layer, gently pressing them into the filling to appear as wriggling worms emerging from the soil.
Repeat the layering process if desired, finishing with a crumb topping and some gummy worms as a final creepy touch.
Serve immediately to enjoy the contrasting textures, or refrigerate for up to 1 hour before serving for a firmer bite.
