Preheat the oven to 350 degrees. Using a food processor or a gallon zip-top bag and your hands. Crush the oreos. Combine the oreo crumbs and the melted butter in the food processor or a bowl.
Pour the oreo butter crumbs into a 9.5-inch pie dish. Using your hands and the bottom of a flat cup, press and form the crumbs into a crust, working the mixture up the sides of the pie dish. Bake for 8-10 minutes. Cool completely.
Using a stand mixer fitted with a paddle or an electric hand mixer on medium-high, whip the cream until stiff peaks form. Set aside.
In a separate bowl, using a stand mixer fitted with a paddle or an electric hand mixer on medium-high beat the cream cheese and peanut butter until completely smooth, scraping down the sides and bottom of the bowl. There should not be any lumps.
Add the sugar and vanilla. Mix on medium until completely incorporated, scraping down the sides and bottom of the bowl.
Add the whipped cream and peanut butter cups. Mix on low until barely combined. Using a spatula, gently fold the mixture a few times. Do not overmix or the whipped cream will deflate.
Spoon the peanut butter filling into the cooled crust. Pop the crust in the freezer if needed before filling. Using an offset spatula or the back of a spoon, smooth the filling to an even layer. Cover and chill in the refrigerator for at least 6 hours. I recommend chilling the pie overnight so the filling can set completely.
Once the filling has set, make the chocolate ganache. In a small saucepan, heat the cream over low. Add the chocolate and stir continuously until the chocolate is mostly melted. When only a few small pieces remain, remove the chocolate ganache from the heat and keep stirring until it is all melted.
Pour the ganache on top of the filling. Pop the pie in the freezer for about 10 minutes so the ganache can set.
Garnish the pie with whipped cream and additional peanut butter cups if desired.