Place Oreos in a large zip-lock bag, seal it shut, and crush them using a rolling pin or sturdy wooden spoon. Aim for chunky crumbles rather than a fine powder. Reserve a small handful for topping.
Spoon 1 1/2 to 2 tablespoons of crushed Oreos into the bottom of each of 6 dessert cups (at least 3/4 cup to 1 cup capacity). Press down gently. Set cups aside.
In a large mixing bowl, beat the softened cream cheese and powdered sugar together with a hand mixer or stand mixer on low speed to start, then increase to medium, until smooth and creamy with no lumps. Start on low to avoid a powdered sugar explosion!
Add vanilla extract and beat until fully incorporated.
Gently fold in the Cool Whip with a spatula using slow sweeping motions until fully combined and fluffy. Do not over-mix.
Fold in the remaining crushed Oreos.
Spoon the cheesecake filling evenly into the 6 prepared cups, pressing gently to fill any gaps around the Oreo base.
Refrigerate for at least 1 hour (or overnight) until set.
Just before serving, top each cup with a swirl of whipped cream, a sprinkle of crushed Oreos, and a whole or half Oreo cookie for garnish.