Before starting, place a medium-sized metal mixing bowl in the fridge or freezer to chill (I like to use metal because it stays colder longer). Chilling the bowl helps the whipped cream set up faster.

Meanwhile, in a food processor, add 28 Oreo cookies. Pulse until a coarse mixture forms. Add the melted butter and continue pulsing until fine crumbs form and mixture is wet. Transfer the crumbs into a 9x9 baking dish. Press down into an even layer, using the back of a measuring cup to help compact the crumbs. Place the crust in the fridge for at least 15 minutes while preparing the filling.

In a large mixing bowl, cream together the room temperature cream cheese and 1 tablespoon powdered sugar. Whip for 2-4 minutes until light and fluffy. Set aside.

Whipped Cream: in the chilled bowl, add the heavy cream, vanilla extract, and the remaining 1 TBSP sugar. Use a stand or hand mixer to beat on medium-high for approximately 2 minutes until firm peaks form.

Make the Filling: Carefully fold the whipped cream into the whipped cream cheese. Crush 8 Oreos and fold them into the filling, then spread it evenly across the Oreo crust.

Place the pan back in the fridge to chill for at least 1 hour before serving. Keep chilled as much as possible for the best results. When ready to serve, crush the remaining 8 Oreos and scatter them across the top of the bars. Then cut into 16 bars, or as many as desired.