In a large bowl, beat cream cheese until smooth. Add powdered sugar and beat well. Fold in half of the whipped topping.

In a separate bowl, whisk together pudding mix and milk.

Set out 12 9 oz. clear cups. Put about a tablespoon of chopped cookies into the bottom of each cup. Divide the cream cheese mixture evenly between the cups (about 2 Tablespoons in each).
Sprinkle on another tablespoon of cookies. Divide pudding between the cups.

Add another tablespoon of cookies. Top each cup with a dollop of the remaining whipped topping. Garnish with a cookie chunk if desired.

Serve immediately or cover and refrigerate until ready to serve.