Make pudding per package directions and let set.
Mix 1/2 cookie crumbs into Cool Whip.
Fill a Ziploc bag with pudding and cut off a small section of one corner.
Squeeze an even layer of pudding on the bottom of the cup.
Fill a bag with Cool Whip mixture and make a layer on top of the pudding.
Use a spoon to evenly spread cookie crumbs for the third layer.
Repeat this layering process until you are to the top of the glass.
Top with a dollop of Cool Whip and a whole Oreo cookie.