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.

close up image of the cross section of chessman banana pudding.

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Not everyone is familiar with this fun dessert – but it’s one that they should be! It’s creamy, delicious, and topped with cookies. What more could you want from a treat?

Using Instant pudding makes this a quick recipe to make, and adding the cookies on top creates a fun texture and unique flavor combination that everyone will love.

This could easily be made for a potluck, holiday dinner, or a fun weekend treat for the whole family to enjoy.

If you’ve been looking for a recipe for the kids to help out in the kitchen, this is a great one to start with! It’s one of my favorite dessert recipes!

close up image of finished chessman banana pudding.

Chessman Banana Pudding

If you’re not in the mood to turn on the oven, this is the treat for you. It’s a simple no-bake recipe that everyone will love – and it’s always fun to give your oven a break.

Using fresh bananas adds a pop of delicious flavor. (Plus, it’s a great way to add some health benefits to your dessert!)

The hardest part of this entire recipe is being patient enough to let it firm up for 4 hours in the fridge. But trust me – it’s worth the wait!

For more pudding recipes, try my Chocolate Pudding Pie with Graham Cracker Crust and my Chocolate Pudding Cake.

ingredients to make chessman banana pudding.

Ingredients for Banana Pudding with Chessman Cookies

See recipe card below this post for ingredient quantities and full instructions.

  • Pepperidge Farm Chessman Cookies – This creates a fun and crunchy top for this pudding dessert.
  • Bananas – They need to be ripe but not mushy.
  • Cream cheese – Soften to room temperature.
  • Sweetened condensed milk – Adds sweetness and helps to thin out the dough.
  • Instant banana pudding mix – This is the main texture of the pudding and also adds that pop of extra banana taste!
  • Vanilla extract
  • Whole milk
  • Cool Whip – If you have this frozen, be sure to thaw before adding.

How To Make Chessman Banana Pudding

  1. Add the cookies: Place one package of the Chessman cookies on the bottom of a 9X13 baking dish. They can overlap a bit.
  2. Add bananas: Top the cookies with sliced bananas in a nice layer.
  3. Mix the ingredients: Beat the softened cream cheese and sweetened condensed milk until smooth.
  4. Add the pudding mix: Add the dry pudding mix to the bowl, and beat again. Then, add the vanilla and milk, and blend until smooth. Scrape down the sides of the bowl to mix evenly.
  5. Fold: Carefully fold in the Cool Whip. Then, spread the mixture evenly over the top of the sliced bananas.
  6. Add more cookies: Top the pudding mixture with the rest of the Chessman cookies.
  7. Cover: Cover the baking dish, and place it in the fridge. Let it chill for a minimum of 4 hours.
  8. Serve: Remove from the fridge. Slice, and enjoy!
close up image of a serving of chessman banana pudding sitting on a white round plate.

Quick Tip

If you want to add the top layer of the cookies right before serving, that is fine, too! This can help to keep them crisp and prevent them from absorbing so much of the banana flavor.

Cover the banana pudding pie with a lid or aluminum foil. Be sure to keep it stored in the fridge, and eat within 3 days. Serve cold!

FAQs

What is a substitute for Chessman cookies?

If you don’t have Chessman cookies, don’t fret! You can swap out the cookies and use vanilla wafers instead.

What makes bananas not turn brown in pudding?

If you’re worried about the bananas browning in the pudding, you can add a little bit of lemon juice to them to stop that from happening.

Otherwise, just know that if they do brown a bit, it doesn’t affect the flavor at all!

What do chessman cookies taste like?

This depends on who you ask. Most people will say that they have a flaky texture and a buttery taste.

Chessman banana pudding in a baking dish with servings missing.

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.
No ratings yet
Course: Dessert
Cuisine: American
Author: Kasey Schwartz
Servings: 20 servings
Prep Time: 15 minutes
Cook Time: 4 hours
Total Time: 4 hours 15 minutes

Equipment

  • 9×13 baking dish
  • Large mixing bowl
  • Electric hand mixer or stand mixer with paddle attachment
  • Measuring cups and spoons
  • Rubber spatula

Ingredients  

  • 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

Instructions 

  • 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!

Nutrition

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
Keyword: Chessman Banana Pudding
Did you make this recipe?Mention @kasey_allthingsmamma or tag #allthingsmamma!

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About Kasey Schwartz

For over 15 years, Kasey Schwartz, the mastermind behind All Things Mamma, has been the ultimate go-to for mouthwatering family recipes. Her work has been featured on Today.com, Buzz Feed, Better Homes and Gardens, and more, making her your go-to mom next door for all things delicious and family-friendly.

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