In a large mixing bowl add the heavy whipping cream, powdered sugar and vanilla. Beat on high speed until soft peeks form. about 3-4 minutes. Refrigerate until ready to use.
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 dallops of whipped cream and place a whole Oreo cookie on top.