In a blender, combine the ice, vanilla milk, espresso, black cherry syrup, mocha syrup, cocoa powder, and ice cream (if using).
Blend until smooth and velvety.
Pour into a tall clear plastic cup, allowing some cherry syrup to drip on the inside for that gothic marble ribbon effect.
Top with whipped cream.
Drizzle with cherry syrup and dust with dark cocoa.
Gently place a mini raven cookie on the whipped cream mound.