Crumble the brownies and set aside.

Blend the ice cream and milk until creamy and thick. If too thick, add a little more milk. Save some of the brownie crumbles for garnish and pulse the rest into the milkshake.

Drizzle some chocolate syrup down the sides of a tall glass, letting a little pool at the bottom. Pour in the milkshake, top with whipped cream, reserved brownie crumbles, and a cherry or two.