Mix the crushed Oreo cookies and melted butter in a bowl. Press this mixture firmly into the bottom and up the sides of a 9-inch pie plate. Place the crust in the freezer while you prepare the filling.
In a large bowl, beat the softened cream cheese, powdered sugar, and vanilla extract until smooth. Set aside.
In a separate bowl, whisk together the instant chocolate pudding mix and cold milk for two minutes until slightly thickened.
Gently fold the prepared pudding mixture into the cream cheese mixture until combined.
In another bowl, beat the cold heavy whipping cream until stiff peaks form. Fold the whipped cream into the cream cheese and pudding mixture until just blended.
Pour the creamy filling into the chilled Oreo crust.
Cover the pie loosely with plastic wrap and refrigerate for at least 4 hours, or until the filling is firm.
Before serving, top the pie with whipped topping and extra crushed Oreos, if desired.
Notes
You can use a food processor to crush the cookies quickly.
For a firmer crust, chill it for 15 minutes before adding the filling.
If you prefer a richer chocolate flavor, use chocolate milk instead of regular milk for the pudding.