Crush the Oreos in a food processor until finely ground. Pour into a mixing bowl with the butter and use a fork to combine. Press mixture into the bottom and up the sides of a greased 9-inch pie pan; refrigerate.
Make the Filling:
In the well-chilled bowl of a stand mixer fitted with a whisk attachment, beat the heavy cream until soft peaks form. Add 1/2 cup of the powdered sugar and vanilla, and continue whipping until stiff peaks form. Transfer whipped cream to another bowl and place in refrigerator to keep chilled.
Return bowl to mixer. Switch whisk attachment out and replace with paddle attachment. Beat 4 ounces of the cream cheese and pudding mix together until combined. Gradually add the milk, a little at a time, allowing mixture to come together after each addition. Beat in 1 cup of the whipped cream until smooth and lightened.
Remove bowl from the mixer and fold in another cup of the whipped cream until just combined. Spread filling evenly into the pie crust.
Clean the bowl and paddle, then return to the mixer. Beat the remaining 4 ounces of cream cheese and 1/2 cup powdered sugar together until smooth. Stir in mint extract. Fold in 1 and 1/2 cup of the whipped cream into the filling, followed by the chopped Oreos.* Spread evenly on top of chocolate layer. Refrigerate at least 4 hours, preferably overnight.
On the day of serving, decorate pie with remaining whipped cream and extra Oreos. Slice, serve, and enjoy!
Notes
*Try to avoid over-mixing when folding in the Oreos--they tend to bleed into the filling, resulting in a not-so-appetizing grayish color.