01 - Preheat your oven to 350°F (175°C). Prepare a 9-inch (23 cm) round cake pan by greasing and lining it with parchment paper.
02 - In a mixing bowl, cream together the softened butter and granulated sugar until light and fluffy. Beat in the eggs one at a time, ensuring each is fully incorporated, then stir in the vanilla extract.
03 - Sift together the all-purpose flour, baking powder, and salt in a separate bowl. Gradually add the dry ingredients to the wet mixture, alternating with the milk. Mix until just combined, being careful not to overmix.
04 - Pour the cake batter into the prepared pan and bake for approximately 20 minutes, or until a toothpick inserted into the center comes out clean. Allow the cake to cool completely.
05 - For the chocolate pasta, combine the all-purpose flour, unsweetened cocoa powder, granulated sugar, and salt in a bowl. Create a well in the center and add the egg and olive oil. Mix until a dough begins to form, gradually adding water a tablespoon at a time until a smooth, kneadable dough is achieved. Wrap the dough and let it rest for 15 minutes.
06 - On a lightly floured surface, roll the rested dough thinly. Cut it into thin noodle-like strips. Bring a pot of salted water to a boil, then cook the pasta strips for 2-3 minutes. Drain the pasta and immediately cool it under cold running water to stop the cooking process.
07 - In a chilled bowl, whip the heavy cream with the powdered sugar and vanilla extract until stiff peaks form. Be careful not to overwhip.
08 - Cut the cooled cake into bite-sized cubes. In individual serving glasses or bowls, layer the cake cubes, cooled chocolate pasta, and whipped cream. Repeat the layers as desired to create a visually 'chaotic' presentation. Finish by topping generously with the crushed Oreo cookies.
09 - Refrigerate the assembled desserts for at least 30 minutes to allow the flavors to meld and the components to set.