Place the chocolate sandwich cookies in a food processor or seal them in a zip-top bag and use a rolling pin to crush them into fine crumbs. Set aside about 1/4 cup of crumbs for garnish.
In a large mixing bowl, beat the softened cream cheese with sugar and vanilla extract until smooth and creamy, about 2-3 minutes. This creates a rich, fluffy base for the pudding layers.
Gradually add the cold milk to the pudding mix, whisking constantly until the pudding is thickened and smooth, about 2 minutes. This creates the chocolate pudding layer.
Gently fold the prepared pudding into the cream cheese mixture until well combined and smooth. This blends the creamy and chocolate layers seamlessly.
Spread half of the cookie crumbs in an even layer at the bottom of your serving dish. Top with half of the pudding mixture, spreading it out smoothly with a spatula.
Add the remaining cookie crumbs in an even layer over the pudding, then top with the rest of the pudding mixture. Smooth the top to create an even surface.
Refrigerate the assembled dirt cake for at least 2 hours to allow the flavors to meld and the layers to set.
Before serving, sprinkle the reserved cookie crumbs over the top for a finishing crumbly look. Immediately garnish generously with gummy worms crawling over the surface and hanging off the sides, creating a playful, messy appearance.
Serve the dirt cake chilled, with gummy worms squirming on top and the layered chocolate look inside. Enjoy the messy, fun dessert with friends and family.
