Add 28 Oreo cookies to a food processor and pulse until fine. Set 2 teaspoons of crumbs to the side for garnish, if desired.
Combine the cookie crumbs and melted butter in a mixing bowl, until the crumbs hold together. Then press the crust mixture on the bottom and up the sides of a 9-inch deep dish pie pan.
Place the Oreo cookie crust in the freezer while you prepare the filling.
Add 14 cookies to a gallon zipper storage bag and seal it. Use a rolling pin to break up the cookies into pebble-sized chunks, and set aside.
Beat 2 cups of cold, heavy whipping cream until stiff peaks form, in a mixing bowl and then gently mix in the sweetened condensed milk.
Next, fold in the pebble-sized cookie pieces and spread the ice cream filling into the prepared, chilled crust.
Spoon fudge over filling in tablespoon spoonfuls.
Then using a knife, gently swirl the fudge into the filing.
Finally, freeze the pie for about 4 hours or until it's firm.
Remove Oreo pie from the freezer about 10 minutes before serving for easier cutting.
If desired, just before serving, beat 1/2 cup heavy whipping cream and 1 tablespoon of powdered sugar until stiff peaks form, and pipe the sweetened whipped cream around the edge of the homemade pie. Then sprinkle with the reserved 2 teaspoons of Oreo crumbs, and garnish with the remaining 6 cookies broken into halves or quarters.