This easy Southern-style banana pudding layers buttery Chessmen cookies, fresh bananas, and a rich, creamy vanilla filling made with instant pudding, cream cheese, and whipped topping. Assemble it ahead, then chill until set for a crowd-pleasing no-bake dessert.
Arrange a layer of Chessmen cookies across the bottom of a 13-by-9-inch baking dish, covering the base as evenly as possible. Reserve the remaining cookies for the top.
In a large bowl, whisk or beat the instant pudding mix with the milk and heavy cream for about 2 minutes, until the mixture begins to thicken. Set aside.
In a separate bowl, beat the softened cream cheese and sweetened condensed milk until smooth and well combined.
Use a spatula to gently fold the whipped topping into the cream cheese mixture, keeping the mixture light and fluffy.
Add the pudding mixture to the cream cheese mixture and stir or fold until the filling is evenly blended.
Slice the bananas and arrange them in an even layer over the cookies. Add a second layer if you prefer extra banana.
Spoon the pudding mixture over the bananas and smooth it into an even layer, spreading it all the way to the edges of the dish.
Arrange the remaining Chessmen cookies over the top. Cover the dish tightly with plastic wrap and refrigerate for at least 4 hours, or overnight, until set and chilled.