Preheat your oven to 350°F (175°C).
Grease and flour two 9-inch round cake pans.
In a large mixing bowl, combine the dry ingredients: flour, sugar, cocoa powder, baking powder, baking soda, and salt.
In another bowl, whisk together the eggs, milk, vegetable oil, and vanilla extract until well combined.
Gradually add the wet ingredients to the dry ingredients, mixing until just combined.
Carefully stir in the boiling water, followed by the crushed Oreo cookies.
Divide the batter evenly between the prepared pans.
Bake for 30-35 minutes or until a toothpick inserted in the center comes out clean.
Let the cakes cool in the pans for 10 minutes, then remove them and cool completely on wire racks.
While the cakes cool, prepare the frosting by beating the softened butter until creamy.
Gradually add the powdered sugar, mixing on low speed until incorporated, then increase speed and add heavy cream until desired consistency is reached.
Fold in the crushed Oreo cookies for added flavor and texture.
Assemble the cake by placing one layer on a serving platter and spreading a layer of frosting on top before placing the second layer.
Frost the top and sides of the cake with the remaining frosting.
Garnish with additional crushed Oreo cookies on top.
Slice, serve, and enjoy!