Crush 18 Oreo cookies finely. Mix with melted butter until well combined.
Press the Oreo mixture firmly into the bottom and up the sides of a 9-inch pie dish. Chill in the refrigerator while preparing the filling.
In a large bowl, beat the softened cream cheese until smooth. Add 1 cup powdered sugar and 1 teaspoon vanilla extract; beat until creamy and well combined.
In a separate bowl, whip the heavy cream with 2 tablespoons powdered sugar and 1/2 teaspoon vanilla extract until stiff peaks form.
Gently fold the whipped cream into the cream cheese mixture until fully incorporated.
Spread the filling evenly into the chilled Oreo crust.
Crush the remaining 6 Oreos and sprinkle over the top of the pie.
Refrigerate for at least 4 hours, or until set, before serving.
Notes
For best results, use full-fat cream cheese and heavy whipping cream. The pie can be made up to 2 days in advance and stored covered in the refrigerator.