Preheat your oven according to the instructions on the brownie mix box. Prepare the brownie batter as directed, using the ingredients specified on the box. Pour the batter into your greased 9x13-inch baking dish and bake until a toothpick inserted in the center comes out with a few moist crumbs. Allow the brownies to cool completely in the pan.
While the brownies are cooling, take your softened cream cheese and mix it with the confectioners' sugar in a medium bowl. Use an electric mixer to blend until smooth and creamy. Gently fold in half of the thawed whipped topping until fully combined.
Once the brownies have cooled, spread the cream cheese mixture evenly over the cooled brownies. Next, sprinkle half of the coarsely chopped Oreo cookies over the cream cheese layer.
In another bowl, whisk together the instant chocolate pudding mix and cold milk until thickened. Pour the pudding over the Oreo layer, spreading it evenly.
Top the pudding layer with the remaining whipped topping, smoothing it out with a spatula. Finally, sprinkle the last of the coarsely chopped Oreo cookies on top.
Cover the dish with plastic wrap and refrigerate for at least 4 hours or overnight to allow the layers to set properly. When you’re ready to serve, slice into squares and enjoy!
