In a large mixing bowl, combine the vanilla pudding mix and banana cream pudding mix with 4 cups of very cold milk. Using an electric mixer, beat the mixture on medium speed for about 2-3 minutes, or until it thickens to a creamy consistency.

In a separate bowl, beat the softened cream cheese until smooth. Add in the vanilla extract, cinnamon, and sweetened condensed milk, mixing until well combined.

Gently fold the cream cheese mixture into the thickened pudding mixture using a spatula until combined. Then fold in one container of Cool Whip.

In a large serving dish, start layering with a third of the pudding mixture, followed by a layer of Chessman cookies and Nilla wafers, topped with sliced bananas and strawberries.

Repeat the layering process with the remaining ingredients, finishing with the remaining pudding mixture for the final layer.

Spread the remaining Cool Whip evenly over the final layer of pudding. Decorate the top with additional strawberries, crushed cookies, and extra glaze if desired.

Cover with plastic wrap and refrigerate for at least 30 minutes, preferably overnight, to allow flavors to meld.