With a food processor, or plastic ziplock bag, crush the Oreos for the crust. Mix with the melted butter. Press the cookie and butter mixture into a pie pan pressing down on the bottom and up the sides. Place in the refrigerator while making the filling.
Pour the heavy whipping cream into a medium mixing bowl. Beat with an electric hand mixer until stiff peaks form. In the other mixing bowl, add the softened cream cheese. Beat until smooth. Add the powdered sugar and vanilla extract and beat until well mixed. Crush 10 Oreos into varying sizes and add the cookies and whipped heavy cream into the bowl with the cream cheese mixture. Gently fold until mixed together.
Remove the pie crust from the refrigerator. Place the creamy filling into the pie crust and smooth with a rubber spatula. Loosely cover the pie with plastic wrap and place in the refrigerator for 3-6 hours before serving.*
Right before serving, garnish with whipped cream and more Oreos.
Notes
You can eat this right away, but it's best if you refrigerate 3-6 hours before serving.
Use a cup or measure cup to press down the Oreo and butter mixture. This will help the crust become more compact.
Cover with plastic wrap and freeze in the freezer for up to one month. Serve frozen or thaw before serving.