Using a food processor grind the Oreo's into fine crumbs. Mix with the melted butter. Press firmly into a 9 inch spring form pan. Set in the freezer while you work on the filling.
In a stand mixer whisk heavy cream until you get soft peaks. Add powdered sugar and vanilla, and mix until stiff peaks. Place in a separate bowl, and set aside.
In the stand mixer bowl, using a paddle attachment, beat together peanut butter, cream, cheese, and sugar until well combined. Using a spatula, gently fold in the whipped cream. Once well mixed, fold in the peanut butter cup Oreo cookie pieces. Pour into prepared crust. Set in fridge for 1 hour.
To make the topping: In a microwave safe bowl heat 1/2 cup heavy cream for 30-45 seconds until hot but not boiling. Add chocolate, and mix until smooth. Pour over the top of the cheesecake.
Top with the rest of the crushed Oreo's. Let sit for 4 hours before slicing to serve.