In a medium mixing bowl, whisk together the instant banana pudding and milk. Cover and refrigerate until thickened.
In a large mixing bowl, beat the cream cheese together with the powdered sugar and vanilla extract until smooth. Reserve ¾ cup of the whipped topping and set aside. Beat the remaining whipped topping into the cream cheese mixture until smooth and creamy.
Line a 3-quart 9x13 inch glass dish with a single layer of the vanilla wafer cookies. Pour the prepared banana pudding recipe over the cookies and gently spread out evenly with a spatula.
Peel the bananas and slice into ½ inch thick rounds. Add the bananas to the dish over the vanilla layer.
Dollop the “cheesecake” mixture over top of the bananas and use a spatula to very gently spread until the dollops meet and the cheesecake layer is evenly spread over all of the bananas.
Top the cheesecake layer with an even layer of the vanilla wafer cookies.
Scoop the reserved whipped topping into a small zip top bag and cut off the corner to create a piping bag. Decorate the top of the dessert with the whipped topping.
Serve immediately or cover and refrigerate before serving to allow the cookies to soften.