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Prep: Line the bottom of a 8x8x2-inch baking dish with lady chessmen cookies. You should be able to get 5 across by 4 down, so 20 cookies per layer.
Make Pudding: In a bowl, combine the milk, pudding mix and blend using a handheld electric mixer until smooth. Set aside and let it set.
Mix & Combine: Using another bowl, combine the cream cheese and condensed milk together and mix until smooth. Fold the whipped topping into the cream cheese mixture. Add the cream cheese mixture to the pudding mixture and stir until well blended.
Assemble: Pour half the mixture over the first layer of the cookies then top with the sliced bananas. Top with remaining cream cheese mixture and spread evenly over the bananas. Finally top with another layer of chessman cookies.
Chill & Serve: Refrigerate for at least a couple hours before serving.