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Chessman banana pudding in a baking dish with servings missing.
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5 from 1 vote

Chessman Banana Pudding

This delicious Chessman Banana Pudding is a fun and simple treat. Made with instant pudding mix, bananas, and a handful of other simple ingredients, this easy dessert is requested time and time again.
Prep Time15 minutes
Cook Time4 hours
Total Time4 hours 15 minutes
Course: Dessert
Cuisine: American
Keyword: Chessman Banana Pudding
Servings: 20 servings
Calories: 215kcal


  • 9x13 baking dish
  • Large mixing bowl
  • Electric hand mixer or stand mixer with paddle attachment
  • Measuring cups and spoons
  • Rubber spatula


  • 2 packages Pepperidge Farm Chessman Cookies
  • 6 bananas ripe and sliced
  • 1 cup cream cheese softened
  • 1 (14 ounce) can sweetened condensed milk
  • 1 (5 ounce) box Instant Banana Pudding
  • 1 teaspoon vanilla extract
  • 2 cups whole milk cold
  • 5 cups (about 12 ounces) Cool Whip thawed


  • Place one package of the Chessman cookies on the bottom of a 9X13 baking dish. They can overlap a bit.
    2 packages Pepperidge Farm Chessman Cookies
  • Top the cookies with sliced bananas in a nice layer.
    6 bananas
  • Beat the softened cream cheese and sweetened condensed milk until smooth.
    1 cup cream cheese, 1 (14 ounce) can sweetened condensed milk
  • Add the dry pudding mix to the bowl and beat.
    1 (5 ounce) box Instant Banana Pudding
  • Add the vanilla and milk and blend until smooth. Scrape down the sides of the bowl to mix evenly.
    1 teaspoon vanilla extract, 2 cups whole milk
  • Carefully fold in the Cool Whip and then spread the mixture evenly over the top of the sliced bananas.
    5 cups (about 12 ounces) Cool Whip
  • Top the pudding mixture with the rest of the Chessman cookies.
  • Cover the baking dish and place in the fridge. Let it chill for a minimum of 4 hours.
  • Remove from the fridge. Slice, and enjoy!


Serving: 1serving | Calories: 215kcal | Carbohydrates: 34g | Protein: 4g | Fat: 8g | Saturated Fat: 5g | Polyunsaturated Fat: 0.5g | Monounsaturated Fat: 2g | Cholesterol: 24mg | Sodium: 199mg | Potassium: 274mg | Fiber: 1g | Sugar: 26g | Vitamin A: 300IU | Vitamin C: 4mg | Calcium: 120mg | Iron: 0.2mg