Prepare the crust: Combine the crushed Oreo cookies and melted butter in a bowl. Press the 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.
Make the cream cheese layer: In a large bowl, beat the softened cream cheese until smooth. Gradually beat in the powdered sugar and vanilla extract until fully combined.
Prepare the pudding: In a separate bowl, whisk the instant chocolate pudding mix with the cold milk for about two minutes until it starts to thicken.
Combine the fillings: Gently fold the prepared chocolate pudding into the cream cheese mixture until just combined.
Fold in whipped topping: Carefully fold in about two-thirds of the thawed whipped topping until no streaks remain. Do not overmix; you want the filling to stay light and airy.
Assemble the pie: Pour the rich chocolate filling into the chilled Oreo crust and spread it evenly.
Chill the pie: Cover the pie loosely with plastic wrap and refrigerate for at least 4 hours, or until the filling is firm.
Finish and serve: Before serving this decadent chocolate dessert, top the pie with the remaining whipped topping and sprinkle with chocolate shavings, if desired. Slice and enjoy your creamy chocolate pie.
Notes
For an even richer flavor, use dark chocolate instant pudding mix instead of regular.
If you prefer a graham cracker crust, substitute 1 1/2 cups of graham cracker crumbs mixed with 1/4 cup sugar and 6 tablespoons melted butter.
You can make this make ahead chocolate dessert the day before serving for the best texture.