Scoop a layer of ice cream in a small, individual-sized trifle bowl or cocktail glass.
Place the brownie on top of the ice cream. Scoop another layer of ice cream on top of the brownie.
Sprinkle a layer of crushed chocolate chip cookies on top of the ice cream.
If needed, repeat layering until you reach the top of the glass. Top with whipped cream and more crushed cookies for garnish. Enjoy!