Preheat the Oven: Preheat your oven to 350°F (175°C). Grease and flour two 9-inch round cake pans and set aside.
Mix the Dry Ingredients: In a large mixing bowl, whisk together flour, cocoa powder, sugar, baking powder, baking soda, and salt.
Add the Wet Ingredients: Add eggs, milk, vegetable oil, and vanilla extract. Mix until well combined.
Incorporate Boiling Water: Gradually add boiling water while stirring. The batter will be thin, but this ensures a moist cake.
Add Crushed Oreos: Gently fold in the crushed Oreo cookies.
Bake the Cake: Divide the batter evenly between the prepared cake pans. Bake for 30-35 minutes or until a toothpick inserted in the center comes out clean.
Cool Completely: Let the cakes cool in the pans for 10 minutes, then transfer them to a wire rack to cool completely.
Prepare the Frosting: Beat the butter until smooth. Gradually add powdered sugar, heavy cream, and vanilla extract, beating until fluffy. Fold in the crushed Oreos.
Assemble the Cake: Place one cake layer on a serving plate. Spread a generous amount of frosting over it. Place the second layer on top and frost the entire cake.
Garnish: Sprinkle crushed Oreos on top and drizzle with melted chocolate.
Serve & Enjoy: Slice and serve your decadent Chocolate Oreo Cake!