Layer the bottom of the pan with a single layer of chessmen cookies, you should be able to fit about 20. Then layer with the sliced bananas.
In a bowl, combine the milk and pudding mix using a hand mixer. Mix until smooth then allow to set.
In a separate bowl using a hand mixer beat the cream cheese with condensed milk (1 minute). With a spatula, scrape down the sides and bottom of the bowl and mix again for 30 seconds.
Fold in the whipped topping into the cream cheese mixture.
Add the cream cheese mixture to the pudding mixture and stir until well combined.
Spread/pour the mixture over the cookies and fresh banana layer in the pan.
Top with the remaining Chessmen cookies, cover with plastic wrap and chill in the fridge overnight (or at least 4 hours).
Use Ripe Bananas: You want to use the perfect bananas that are yellow and have just started to turn brown. They should be sweet, but still firm when you slice them.
If the pudding seems runny: Don’t worry. It will finish setting up in the refrigerator. You don’t need to let the instant pudding set all the way before adding in the cream cheese and sweetened condensed milk, but it’s ok if it does. Refrigerating banana pudding before serving it is key to getting a perfectly set no-bake dessert.
Have broken cookies? It’s possible that some of your Chessman cookies will be broken in the bag. Open both bags in the beginning, and pull out the broken ones to use as the bottom layer.
Make a smaller portion: This recipe serves a group and is best eaten within a day or two, so if you’re cooking for less than 5 people, you may want to halve the recipe. You can do this by halving the ingredients and assembling them in an 8x8 pan.
To Store: Banana pudding should be stored, covered, in the refrigerator. This dessert is best eaten within two days of making it. The bananas will start to get brown after that.