Preheat the oven to 325 degrees F. Line a 8x8 baking pan with parchment paper, leaving about 2 inches overhang (so that you can easily remove the brookies once they're done).
First, we're going to make the chocolate chip cookie dough. Melt butter in the microwave, then add in the brown sugar and sugar. Whisk together for about 1 minute, until combined, then add in the egg and vanilla extract. Continue to mix until combined, about 30 seconds. 12 tbsp Salted Butter3/4 cup Brown Sugar1/3 cup Sugar1 tbsp Vanilla Extract1 tbsp Vanilla Extract
Use a rubber spatula to fold in the all purpose flour, baking powder, baking soda, and kosher salt. Mix until a dough begins to form, then add in the chocolate chips. Mix to combine and set aside. 2 1/4 cups All Purpose Flour2 tsp Cornstarch1/2 tsp Baking Soda1/2 tsp Baking Powder1/2 tsp Kosher Salt1 cup Semi-Sweet Chocolate Chips
Now make the brownie batter. Add semi-sweet chocolate and butter to a large microwave safe bowl. Microwave for about 40 seconds, until the butter is melted, then whisk together (it's ok if everything is not fully melted). Microwave again in 15 second increments, whisking in between, until the chocolate is fully melted. Add in oil, cocoa powder, and espresso powder and whisk to combine, then set aside. 4 oz Semi-Sweet Chocolate10 tbsp Salted Butter1/4 cup Vegetable Oil3/4 cup Cocoa Powder1 tsp Espresso Powder
In a separate bowl, add the eggs, egg yolk, brown sugar, and sugar. Use an electric mixer and beat together for 3 minutes on medium speed until frothy and sugar is dissolved (you'll know the sugar is dissolved when you rub a little bit of the mixture between your fingers and it's no longer gritty. 3 large Eggs1 Egg Yolk3/4 cup Brown Sugar1/2 cup Sugar
Pour in the chocolate mixture and vanilla extract and continue to mix until combined, about 30 seconds. Scrape down the side of the bowl to ensure everything is fully combined, then add in the all purpose flour, cornstarch, and kosher salt. Use a rubber spatula to combine, then add in the chocolate chips. 2 tsp Vanilla Extract3/4 cup All Purpose Flour 3 tbsp Cornstarch 1/2 tsp Kosher Salt 1 cup Semi-Sweet Chocolate Chips
Add half of the brownie batter to the prepared pan to form the brownie layer. Add in half of the chocolate chip cookie dough and spread into an even layer. Add the remaining brownie batter on top, ensuring all of the cookie layer is covered. Roll the remaining cookie dough into balls (it doesn't matter the size, I did about 9 balls) and place them on top of the brownie batter.
Bake for 40-45 minutes, until the edges are set and the center has the slightest jiggle, like jello.
Allow the brookies to cool to room temperature for about 30 minutes, then place into the refrigerator to set for about 4 hours. (for an extra gooey brownie, you can eat them immediately. for super fudgy brownies, refrigerate to set)