Chessmen Banana Pudding

chessmen banana pudding

When my son was born, one of my good friends brought me a meal.   The dinner was delicious but what stood out most for me was the big pan of delicious banana pudding complete with those cute little Chessmen cookies decorating the top.

Of course, I had to get the recipe.

Since then I have made this Chessmen Banana Pudding for many potlucks.   It always gets devoured!   Even people that don’t typically like banana pudding love this pudding and come back for seconds.

Of course, my kids lick their plates clean and beg for more too.

Not only does it taste wonderful but it is so easy that now my son can make it all by himself.   Score!

Chessmen Banana Pudding


2 bags Pepperidge Farm Chessmen cookies

6 to 8 bananas, sliced

2 cups milk

2 (3.4-ounce) boxes instant French vanilla pudding

1 (8-ounce) package cream cheese, softened

1 (14-ounce) can sweetened condensed milk

1 (8-ounce) container Cool Whip, thawed


1. Cover the bottom of a 13×9 inch baking dish with a bag of Chessmen cookies.

2. Layer the bananas on top of the cookies.

3. Combine the milk and pudding mix. I use my largest mixing bowl for this because everything will be added to it in the end.   Blend well using a handheld mixer.   This is my son’s favorite part!

cool whip Collage

4. Using another bowl, combine the cream cheese and condensed milk together and mix until smooth. We use the stand mixer for this just to be sure all the little bits of cream cheese are well blended.

5. Fold the Cool Whip into the cream cheese mixture.   Yum!

cool whip

6. Add the cream cheese mixture to the pudding mixture and stir until well blended.   This is why you want to start with your largest bowl when making the pudding mixture!

7. Pour the mixture over the cookies and bananas and cover with the remaining Chessmen cookies.

8. Refrigerate overnight to let the pudding soak into the cookies.   Yeah right!   We just grab a spoon and dig in as soon as the last cookie goes on top!

chessmen pudding

I still use my friend’s handwritten, now pudding splattered, recipe each time I make it but I recently discovered that my top-secret-oh-so-awesome-secret-recipe is not really a secret recipe after all.   It is a recipe by Paula Deen on Food Network!  

Over the years I have had to make some minor adjustments to Paula’s original recipe simply because product manufacturers have changed the size of the product they sell.   However, this recipe is so forgiving that you can make adjustments to it here and there and it still turns out incredible.

This is one of our favorite dessert to dollop with COOL WHIP.

What do you dollop?

Reply below for a chance to win $500 cash! Visit the COOL WHIP Facebook page to see more recipes and share your creations!

This is a sponsored conversation written by me on behalf of COOL WHIP. The opinions and text are all mine. Official Sweepstakes Rules.