In a blender, combine the chocolate ice cream, whole milk, and chocolate syrup. Blend until smooth and creamy. If the mixture is too thick, add a little more milk to reach your desired consistency.
Drizzle chocolate syrup inside the glasses you will be using for the freakshake.
Pour the chocolate shake mixture into the prepared glasses, filling them about three-quarters full.
Top each shake with a generous dollop of whipped cream.
Sprinkle chocolate chips, crushed chocolate cookies, and chocolate sprinkles over the whipped cream.
Garnish with chocolate-covered pretzels and a piece of chocolate bar.
Finish with a maraschino cherry on top. Serve immediately with a straw and enjoy!