Combine the 16 oz cream cheese, 1 teaspoon vanilla and ½ cup sugar on medium speed. Cream until smooth.
Fold in 8 oz Cool Whip until thoroughly combined.
Add in ½ cup crushed Oreo pieces and fold to combine.
Transfer the cheesecake filling to a piping bag. Set aside until ready to use.
Combine 1 cup powdered sugar and ¼ cup milk in a small bowl and whisk to combine.
Use the piping bag to pipe a large dollop of cheesecake filling into each cone.
Insert one half on an Oreo into the top of each cone.
Drizzle each cone with some glaze.
Sprinkle each cone with additional Oreo crumbs.
Notes
Tips + StorageFilling will soften cones, so assemble within a few hours of serving.These can be stored, assembled for about 1 day covered in the fridge. If unassembled, the filling can be kept in an airtight container for 2 - 3 days.