Preheat the oven to 350°F. Lightly spray two round 8” baking pans with cooking spray and line it with parchment paper. Spray the parchment paper.
In a medium bowl, combine the sugar, flour, cocoa powder, powdered sugar, chocolate chips, and salt.
In a large bowl, whisk together the eggs, olive oil, water, and vanilla.
Add the dry mix to the wet mix and stir until just combined.
Pour the batter into the prepared pan and use a spatula to smooth the top. Bake for 22-25 minutes or until a toothpick comes out with only a few crumbs attached (note: it's better to pull the brownies out early than to leave them in too long). Cool completely. Remove from pans so that you can use the same pans for the next layers.
COOKIE DOUGH LAYER
In a large bowl, combine butter with the brown and granulated sugar. Stir to combine. Stir in the milk, vanilla, and salt until well blended. Stir in the flour until completely smooth.
Stir in chocolate chips.
Line two round 8”baking pans (the same ones you used with the brownie layers) each with a piece of parchment paper; this will help to easily remove the cookie dough.
Make 6 small cookie dough balls about 1" wide. Set aside.
Press half of the remaining dough into each pan and use your hands to press it into an even layer.
Place pans of cookie dough pans and cookie dough balls in freezer for at least 30 minutes.
COOKIE DOUGH FROSTING
Blend butter, sugars, vanilla and heavy cream in large mixing bowl until light and fluffy.
Add flour and pinch of salt Blend until light and fluffy.
Stir in chocolate chips.
ASSEMBLY
Using an 8" springform pan, start by adding one brownie layer.
Add frozen cookie dough layer on top of brownie.
Carefully, spoon all 6 cups of softened ice cream on top of cookie dough and spread with a spatula. *You can soften the ice cream by leaving on the counter for 10 minutes.
Add the second frozen cookie dough layer on top of ice cream. Gently push down.
Add the second brownie layer on top of cookie dough.
Complete the cake by spreading cookie dough frosting on top. Add cookie dough balls you reserved earlier for decoration.
Notes
If you are short on time, you can use brownie mix in the box and I won’t judge you at all. I’m sure it will taste excellent whether you made from-scratch brownies or boxed brownies. You do you.