In a large bowl, combine the brownie mix, melted butter, milk and eggs until combined. Set aside.
Press the cookie dough into the bottom of a 10-inch cast-iron skillet. Lay the sandwich cookies in a single layer on top. Drizzle over the caramel sauce, getting into the spaces between the cookies. Pour over the brownie batter and smooth the top.
Bake until set, 40 to 45 minutes. Allow to cool for 20 minutes.
Top the brownie with scoops of the ice cream, then drizzle over the chocolate sauce and garnish with the whipped cream, sprinkles and cherries.