While the cookie crust bakes and cools, make the brownie batter. In a medium bowl, mix together 1 1/2 cups of sugar, 3/4 cup of flour, 2/3 cup of cocoa powder, 1/2 cup of powdered sugar, 1/2 cup of chocolate chips, and 1/2 tsp of salt.
In a large bowl, whisk together 2 large eggs, 1/4 cup vegetable oil, 1/4 cup melted butter, 2 Tbsp water, and 1 tsp vanilla.
Pour the dry mix into the wet ingredients and stir until just combined. The mixture will be pretty thick, but that's how it's supposed to be!
Pour the batter over the shortbread crust in the prepared pan and smooth it into an even layer. Bake at 325°F/163°C for 38-43 minutes. You'll know they're done when they have a set outer edge and a slight jiggle in the center, or when a toothpick inserted halfway between the edge and center comes out with moist crumbs, not batter.
Set on a wire rack to cool fully before topping. If you want to accelerate the process, place the pan in the freezer for 30 minutes.