Preheat oven to 350°. Line a 9x13” pan with foil and spray with cooking spray.
Make the Brownies: Place the baking chocolate and butter in a large, microwave safe bowl. Heat on HIGH power for 2-3 minutes, stirring every 30 seconds, until chocolate is smooth. Stir in sugar. Add eggs, vanilla, and cocoa and stir well. Add flour and stir carefully.
Make the Cookies: Cream together butter and sugars in the bowl of a stand mixer or in a large bowl using a hand mixer. Mix in egg, extract, baking soda, and salt. Stir in flour, then stir in chocolate chips.
Spread brownie batter in prepared pan. Scoop tablespoons of cookie dough, flatten slightly with your hands and then lay over the top of the brownies. It’ll be hard to spread because it’s thicker than the brownie batter, so it’s best to drop flattened tablespoons evenly over the batter and then press lightly with your fingers to adhere them to each other.
Bake for 28-35 minutes until the tops are dark golden. If you test them with a toothpick in the center, the brownies won’t be totally done, so just take them out once the tops are dark golden in color.