Prepare the pan. Line an 8-inch by 8-inch baking pan with parchment paper, leaving an overhang on two sides for easy removal.
Make the Oreo crust. Crush 24 Oreo cookies into fine crumbs using a food processor or rolling pin. Combine the crumbs with 5 tablespoons of melted butter and mix until evenly coated.
Press the crust. Transfer the Oreo mixture to the prepared baking pan. Press firmly into an even layer using the bottom of a measuring cup. Refrigerate for 15-20 minutes while preparing the filling.
Beat the cream cheese. In a large mixing bowl, beat softened cream cheese with an electric mixer until smooth and creamy, approximately 1-2 minutes.
Add sugar and vanilla. Add powdered sugar and vanilla extract. Continue beating until completely smooth and combined.
Whip the heavy cream. In a separate bowl, beat cold heavy whipping cream with an electric mixer until stiff peaks form, approximately 2-4 minutes.
Combine the filling. Gently fold the whipped cream into the cream cheese mixture in several additions until smooth and fluffy.
Add the Oreos. Fold in the 10 chopped Oreo cookies until evenly distributed throughout the cheesecake filling.
Assemble the cheesecake. Spread the filling evenly over the chilled Oreo crust. Smooth the top with a spatula.
Chill. Cover and refrigerate for at least 6 hours, or preferably overnight, until the cheesecake is firm enough to slice.
Slice and serve. Lift the cheesecake from the pan using the parchment paper handles. Cut into 16 bars using a sharp knife, wiping the blade between cuts. Top with extra Oreo crumbs, if desired, and serve chilled.