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A fun twist on a classic, Chessman Banana Pudding swaps the Nilla wafers for buttery shortbread! And since it’s made with instant pudding mix, bananas, and a handful of other simple ingredients, it’s an easy crowd-pleaser you can whip up anytime.
For more ways to enjoy classic banana pudding flavor, try my Banana Pudding Cookies, Banana Pudding Cheesecake, and Banana Pudding Poke Cake.
Why you’ll love this banana pudding recipe with chessman cookies!
Consider this Banana Pudding 2.0! While Nilla wafers in homemade banana pudding are good, Chessman cookies add a little more decadence since they’re so fabulously buttery.
Other than that, this recipe is a pretty traditional recipe made with instant pudding and Cool Whip for ease. It’s great for potlucks and backyard get-togethers, but easy enough to make as a fun weekend treat for the whole family to enjoy!
- A Delicious Upgrade to a Classic: The chessman cookies banana pudding version adds a buttery, melt-in-your-mouth texture that takes things to the next level.
- No-Bake and Super Easy: With instant pudding and simple ingredients, this dessert comes together quickly—no oven required.
- Creamy and Dreamy Layers: From the smooth pudding mixture to the soft bananas and tender cookies, every bite is full of flavor and texture.
- Make-Ahead Friendly: It actually tastes better after chilling, making it ideal for prepping in advance.
Table of Contents
Notes on Ingredients
See recipe card below this post for ingredient quantities and full instructions.
- Pepperidge Farm Chessman Cookies – Buttery shortbread cookies that replace traditional wafers.
- Bananas – Ripe but firm for the best texture.
- Cream cheese – Adds richness and a slight tang.
- Sweetened condensed milk – Sweetens and smooths the filling.
- Instant banana pudding mix – The base of the creamy layer.
- Vanilla extract – Enhances the flavor.
- Whole milk – Helps create a smooth pudding consistency.
- Cool Whip – Makes the filling light and fluffy.
How to Make Banana Pudding With Chessman Cookies
- Layer the cookies: Arrange one package of Chessman cookies in the bottom of a 9×13 baking dish, slightly overlapping if needed.
- Add the bananas: Slice the bananas and layer them evenly over the cookies.
- Make the filling: Beat the cream cheese and sweetened condensed milk until smooth. Add the pudding mix, then the vanilla and milk, mixing until fully combined.
- Fold in the topping: Gently fold in the Cool Whip until the mixture is light and creamy.
- Assemble: Spread the pudding mixture evenly over the bananas.
- Top it off: Add the remaining Chessman cookies on top. Cover and refrigerate for at least 4 hours before serving.
How to Store
Cover with plastic wrap or transfer leftovers to an airtight container. It will last up to 3 days in the refrigerator; I don’t recommend freezing this recipe because the bananas will get mushy, as will the cookies.
Frequently Asked Questions
The buttery shortbread cookies replace traditional wafers, making the dessert richer and more decadent.
Yes! It’s actually better when made a few hours in advance so the flavors can meld.
Cool Whip is more stable, but you can use whipped cream if serving the same day.
More Banana Recipes You’ll Love
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Chessman Banana Pudding
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!
Hello,
Instead of using Cheseman cookie, I used golden oreos. Different feedback with the oreos. Some said it was too sweet. Some really loved it. Now I’m going to try it with Nilla Wafers. It turned out really good.
I will be using your recipe this weekend! Do you think it would be ok to make my own whipped cream in lieu of the cool whip?
We find Cool Whip is best as it’s a little sturdier, but we’d love to know how it goes if you try it out!