Chill the cookies, brownie cubes and two large glasses in the freezer for 10 minutes.

Spread chocolate frosting around the outer glass rims and press the cookie crumbs into the frosting.

Blend the milk, chocolate syrup, ice cream, 2 cookies and 1/2 cup brownie cubes for 18 seconds until spoon-thick.

Pour into the prepared glasses and top each with 1/2 cup whipped cream.

Press the remaining cookie halves and brownie cubes securely into the whipped cream and serve immediately with spoons.