Place Oreo cookies in a blender or food processor and pulse until they turn into fine crumbs. Combine the crumbs with melted unsalted butter in a medium bowl and mix until fully coated. Press into a pie pan and refrigerate for 10 minutes.

In a large mixing bowl, combine the instant vanilla pudding mix and heavy whipping cream. Whip on medium speed until thickened, about 3-5 minutes.

Gently fold in the Cool Whip and finely chopped Oreos until the mixture is smooth.

Spread the filling over the chilled Oreo crust, smoothing it out. Cover with plastic wrap and refrigerate for 4-8 hours.

Whip heavy cream, powdered sugar, and vanilla extract in a chilled bowl until stiff peaks form, about 3-5 minutes.

Remove the pie from the refrigerator, dollop whipped cream on top, sprinkle crushed Oreos, slice, and serve chilled.