Add cookies to a food processor. Pulse until they are smooth crumbs. Pour in butter. Pulse until combined. Pour mixture into a greased 9" pie dish. With the back of a cup, press until 1/4" thick, around the bottom and sides of the dish. Set aside.
In a stand mixer or using an electric mixture, combine peanut butter, cream cheese, vanilla, sugar, and whipped topping until smooth. Spoon into prepared pie crust and smooth. Chill while ganache is made.
Heat cream over medium heat until steaming, but not boiling. Place chocolate in a heat safe bowl. Once cream is hot, pour over chocolate. Whisk constantly until smooth. Allow mixture to cool for 5 minutes.
Pour ganache over pie. Working quickly so it doesn't set, add chopped peanut butter cups. Largest on the outside, working inwards with smaller pieces.
Cover, and chill for at least 2 hours before serving.
Notes
Chill the pie between layers to help it set faster.