Preheat your oven to 350°F and grease a 9-inch springform pan. In a large mixing bowl, cream together 1 cup softened butter and 1 1/2 cups granulated sugar until light and fluffy, about 3 minutes with an electric mixer.
Beat in 2 eggs one at a time, then mix in 2 teaspoons vanilla extract until fully incorporated. In a separate bowl, whisk together 2 cups flour, 2/3 cup cocoa powder, 1 teaspoon baking soda, and 1/2 teaspoon salt.
Gradually add the dry ingredients to the wet ingredients, mixing just until combined. Fold in 1 cup chocolate chips, then spread the thick batter evenly into the prepared springform pan.
Bake for 25-30 minutes until the brownie base is set and a toothpick inserted into the center comes out with moist crumbs. Let the brownie cool completely in the pan on a wire rack, about 1 hour.
While the brownie cools, make the frosting by beating 16 ounces softened cream cheese with 1 cup powdered sugar until smooth. In another bowl, whip 2 cups heavy cream to stiff peaks, then fold it gently into the cream cheese mixture until no white streaks remain.
Spread half of the cream cheese frosting over the cooled brownie base. Sprinkle 1 cup of coarsely crushed Oreo cookies evenly over the frosting layer.
Carefully spread the remaining frosting over the Oreo layer, then top with the remaining crushed Oreo cookies, pressing them lightly into the frosting. Refrigerate for at least 4 hours or until fully set before removing the springform ring and slicing.