Preheat your oven to 350°F. Grease and flour two 9-inch round cake pans.
In a large bowl, mix together flour, sugar, cocoa, baking powder, baking soda, and salt.
Add milk, vegetable oil, eggs, and vanilla to flour mixture and mix together on medium speed until well combined.
Reduce speed and carefully add boiling water to the cake batter until well combined.
Divide the cake batter evenly between the two prepared cake pans and bake for 30-35 minutes, until a toothpick inserted comes out clean.
Remove from the oven and allow to cool for about 10 minutes, then remove from pans and cool completely.
While the cakes are cooling, make the frosting by beating butter until light and fluffy. Gradually add powdered sugar and continue beating until well combined. Stir in vanilla and crushed Oreos until your frosting is smooth and spreadable.
Once the cakes are cooled, spread frosting on the top of one cake layer, place the second cake layer on top, and then frost the outside of the cake.
Garnish with additional Oreo cookies or cookie crumbs if desired, then slice and serve.