Make the Oreo Crust: Place the Oreo cookies in a food processor and pulse until they become fine crumbs.
Add the melted butter and pulse until the mixture resembles wet sand.
Press the crumb mixture firmly into the bottom and up the sides of a 9-inch pie dish.
Use the bottom of a measuring cup to pack it evenly.
Place the crust in the freezer while you prepare the filling (or chill for 15–20 minutes).
Prepare the Peanut Butter Filling: In a large bowl, beat the cream cheese and peanut butter together with an electric mixer until smooth and creamy (about 2 minutes).
Add the powdered sugar and vanilla extract. Beat until fully combined.
In a separate bowl, whip the cold heavy cream until stiff peaks form.
Gently fold the whipped cream into the peanut butter mixture until no streaks remain. The filling should be light and fluffy.
Assemble the Pie: Spread the peanut butter filling evenly over the chilled Oreo crust.
Smooth the top with a spatula.
Refrigerate for at least 1 hour to help it set before adding the ganache.
Make the Chocolate Ganache: Place the chocolate chips in a heat-safe bowl.
Pour the heavy whipping cream over the chocolate chips; let sit for 2–3 minutes.
Pour the mixture into a saucepan and heat gently over low heat until the chocolate is melted and smooth. Alternatively, microwave in intervals if preferred.
Strain to remove any chunks.
Spread the chocolate ganache over the cooled peanut butter filling.
Refrigerate the pie for at least 1 hour before serving.