Add your vanilla pudding and banana cream pudding mix to a large bowl, then pour in the cold milk. Use an electric mixer and blend the milk in with the pudding mixture until it is fully combined and the pudding begins to thicken. This will take about 2-3 minutes.

Once the pudding is thickened, set it aside. Add the softened cream cheese to a separate bowl, along with the vanilla extract, the cinnamon, and the sweetened condensed milk. Blend the cream cheese mixture on high speed until it is smooth and creamy and there are no more lumps.

Pour the cream cheese mixture into the prepared pudding mix and use a spatula to gently combine them together. Fold one of the containers of cool whip into the pudding mixture, careful not to over mix it (you want to keep it nice and fluffy).

Add a little bit of the pudding mixture to the bottom of your dish, then add a layer of the chessman cookies, a layer of the nilla wafers, a layer of bananas, and a layer of strawberries. If you are using a clear bowl or dish, layer some of the strawberries on the edge of the dish for presentation purposes.

Drizzle some of the strawberry glaze over the top of the layers, now ladle in another layer of the pudding mixture. Continue layering the cookies, bananas, strawberries, and strawberry glaze until you get to the top of the dish or you run out of ingredients.

Once you get to the final layer of pudding, add the cool whip topping on top and spread it out in one even layer. Decorate the top of the pudding with leftover strawberries and crushed up nilla wafers and any leftover strawberry glaze.

Lightly cover the pudding with plastic wrap and refrigerate for at least 30 minutes (or preferably overnight) before serving.