In a large mixing bowl add the heavy whipping cream, powdered sugar and vanilla. Beat on high speed until soft peaks form. about 3-4 minutes. Refrigerate until ready to use.
For the Oreo crust
Pulse the cookies including the filling in a food processor until crumbs form
Place the crumbs into a bowl and add the melted butter. Mix until combined and press into a pie dish using a wooden spoon or the bottom of a glass.
Cheesecake filling
Place 18 Oreos in a large ziplock bag and using a rolling pin or cup gently break up Oreos into small chunks.
In a medium bowl add softened cream cheese and 1/2 cup powdered sugar. Beat until creamy. Fold in 2 cups whipped cream and crumbled Oreos.
Spread oreo mixture into Oreo pie crust. Chill at least 6 hours before serving
In a piping bag or sandwich baggie, cut a hole in the corner. Add the star tip into the corner and add the whipped cream into the piping bag. Gently place dollops of whipped cream and place a whole Oreo cookie on top.
Video
Notes
Dont overmix the oreos, or else your filling will turn more grey from the black cookies.You can also purchase a premade oreo crust if you prefer.