1. Process ice cream and milk in a blender until smooth, stopping to scrape down sides.
2. Divide half of ice-cream mixture evenly among 4 (8-oz.) glasses. Top each with 1 Tbsp. fudge topping and 1 Tbsp. caramel topping. Repeat layers with remaining ice-cream mixture and fudge and caramel toppings.
3. Top each with instant whipped cream; sprinkle with 1 Tbsp. crumbled brownies, and top with a cherry. Serve immediately.
Note: For testing purposes only, we used Häagen-Dazs Vanilla Bean Ice Cream and Smucker's Hot Fudge and Caramel Flavored Toppings.