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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.
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Pin RecipeA New Way to Do Banana Pudding
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 Layered Banana Pudding 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!
My Tips for Perfect Chessman Banana Pudding
This recipe is easy as can be, but I have some extra pointers to make sure it turns out perfect!
- It doesn’t HAVE to be Chessman. I do like using Chessman cookies because the rectangular shape works so well for a sliceable banana pudding, but Girl Scout Trefoils or even homemade Shortbread Cookies will work too.
- Don’t use over-ripe bananas. We’re not making Banana Bread here! Brown bananas are too mushy for using in banana pudding. You want bananas that are ripe enough to be sweet while still holding their shape.
- Soften the cream cheese to room temperature. If it’s straight out of the fridge, it will stick to your beaters and be difficult to blend into the rest of the ingredients.
- Keep the cookies crisp. If you want to add the top layer of Chessman right before serving, this will keep them crisp. But if you like them softer, add them when you’re assembling the banana pudding.
How to Store
Cover Chessman banana pudding pie 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.
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!
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!