Preheat the oven to 350 degrees. Grease two 6-inch round cake pans and line the bottoms with parchment paper.
In a large bowl, whisk together the flour, cocoa powder, sugar, and baking powder until evenly mixed.
Add the eggs, vegetable oil, milk, and vanilla extract to the dry ingredients. Stir until the batter is smooth and no dry streaks remain.
Divide the batter evenly between the prepared pans. Bake for 25 to 28 minutes, or until a toothpick inserted in the center comes out clean. Let the cakes cool in the pans for 10 minutes, then transfer to a wire rack to cool completely.
While the cakes cool, whisk the pudding mix with the 2 cups cold milk in a medium bowl until it thickens, about 2 minutes. Set aside.
Whip the heavy cream in a separate bowl until soft peaks form.
Place one cooled cake layer on a serving plate. Spread half the pudding over it. Add the second cake layer and spread the remaining pudding on top.
Sprinkle the crushed Oreos evenly over the pudding to create the dirt layer. Arrange the gummy worms on top before serving.