Prepare brownies according to package instructions and cut out round pieces to fit inside a waffle bowl using a cookie cutter. Tip: make sure the brownies are under-baked. Overcooked brownies will make eating the sundae difficult to eat without breaking the waffle bowl.
Prepare the waffle bowls by melting the chocolate according to package instructions. Place the melted chocolate in a shallow bowl that is wide enough to dip the top of the waffle bowls in. Dip each bowl into the melted chocolate and sprinkle sprinkles around the edge while the chocolate is still warm. Set the bowls aside to allow the chocolate to set.
When the chocolate on the bowl has hardened, place the round brownie pieces inside each bowl.
Top the brownie with a scoop of ice cream. Drizzle chocolate syrup over the ice cream and top with additional sprinkles and a cherry.