Prepare the pudding mixture: In a mixing bowl, whisk together 2 boxes of Instant Pudding Mix and 2 cups of cold milk. Ensure there are no lumps. Once well combined, refrigerate the mixture for about 30 minutes to set.
Make the cream cheese blend: In another bowl, use an electric mixer to beat 8 oz of softened cream cheese until smooth. Gradually add 14 oz of sweet condensed milk and 1 tsp of vanilla extract. Beat until fully combined. Gently fold in 8 oz of Cool Whip until it's light and airy, careful not to deflate it.
Combine the mixtures: Once the pudding has set, fold in the cream cheese blend. Mix until everything is smooth and well incorporated.
Layer the ingredients: In a large serving dish, place a layer of 2 boxes of vanilla wafers at the bottom. Pour a layer of the pudding mixture over the wafers, followed by a layer of 4 sliced ripe bananas. Repeat the layers twice more, finishing with a layer of the pudding mixture on top.
Chill the dessert: Cover the dish and refrigerate overnight. This allows the flavors to meld beautifully.
Serve and garnish: Before serving, optionally top with Chessman cookies and drizzle with caramel for an extra touch of sweetness. Enjoy your refreshing and delightful dessert!