Preheat your oven to 350°F and lightly grease your cast iron skillet if needed.
In a heat-safe bowl, melt the butter and semisweet chocolate chips together until smooth, then set aside to cool slightly.
In a separate bowl, add the granulated sugar, brown sugar, salt, and eggs, and whip the mixture with a hand mixer for about 5 minutes until it becomes pale, thick, and slightly fluffy.
Mix in the vanilla extract, then slowly pour in the melted chocolate and butter mixture, stirring until fully combined and glossy.
Sift in the cocoa powder and flour, then gently fold until just combined and no dry streaks remain. Do not overmix.
Pour the brownie batter into the prepared cast iron skillet and spread it into an even layer.
In a separate bowl, add the browned butter, brown sugar, and granulated sugar, and mix until smooth and well combined.
Add the eggs and vanilla extract to the cookie dough mixture and mix until fully incorporated.
In another bowl, whisk together the flour, baking soda, salt, and espresso powder, then gradually add the dry ingredients into the wet ingredients until a soft dough forms.
Fold in the chocolate chips until evenly distributed throughout the dough.
Let the cookie dough chill for at least 30 minutes in the refrigerator.
Scoop chunks of cookie dough and place them evenly over the brownie layer, leaving some gaps so the brownie layer can peek through.
Bake for 30–35 minutes, or until the top is golden brown and the center is set but still slightly soft for that gooey texture.
Allow the brookie to cool in the skillet for 20–30 minutes before serving so it can set slightly while staying warm and melty.
Scoop and serve straight from the skillet, and enjoy the perfect mix of fudgy brownie and soft cookie in every bite.