I am so excited to share this with you because you are about to find out why this dessert is a total legend in Southern kitchens. Paula Deen’s Chessmen Cookie Banana Pudding is not your basic pudding at all. It swaps out those regular vanilla wafers for these buttery shortbread Chessmen cookies and it creates this velvet texture that just melts in your mouth. I remember the first time I made this for a family party and people were literally scraping the bottom of the dish just to get every single drop of that cream cheese filling. It is so rich and decadent but I promise it is surprisingly simple to put together.

Why You Will Love Paula Deen’s Chessmen Cookie Banana Pudding

You are going to love this recipe because it uses a secret combination of cream cheese and sweetened condensed milk. This mix creates a thick and cheesecake like consistency that stays firm way better than traditional pudding does. You will love the contrast between those soft bananas and the buttery crunch of the cookies. It is the perfect dessert to make ahead of time for potlucks or holidays because the flavor actually gets better as it sits in the refrigerator.

Ingredients for Paula Deen’s Chessmen Cookie Banana Pudding

Go ahead and gather these simple items to create your masterpiece. Just make sure your cream cheese is at room temperature so you do not get any lumps in your mixture.

2 bags of Pepperidge Farm Chessmen cookies
6 to 8 bananas sliced into rounds
2 cups whole milk
1 box of instant vanilla pudding mix which is 5 ounces
1 package of cream cheese at 8 ounces and softened
1 can of sweetened condensed milk at 14 ounces
1 container of frozen whipped topping at 12 ounces and thawed

How to Make Paula Deen’s Chessmen Cookie Banana Pudding

You need to follow these steps carefully. Most people get confused during the mixing stage so really pay attention to the order of operations here.

Step 1: Prepare the Base Layer

Take a 13 by 9 inch baking dish and line the bottom with one bag of the Chessmen cookies. I try to fit them as tightly as I can so they form a nice solid crust for the pudding.

Step 2: Layer the Bananas

Now you want to place your sliced bananas directly on top of those cookies. Use enough bananas to cover the cookies completely because this ensures every single bite has that fresh fruit flavor we want.

Step 3: Mix the Pudding

Grab a medium bowl and combine the milk with the instant vanilla pudding mix. Use a hand mixer to blend them until the mixture starts to get thick. This usually takes me about two minutes of active mixing.

Step 4: Combine the Cream Mixture

In a separate large bowl you need to beat the softened cream cheese and the sweetened condensed milk together until the texture is completely smooth. Once it looks good you can gently fold in the thawed whipped topping using a spatula.

Step 5: Assemble the Pudding

Now add your prepared pudding mixture into that cream cheese mixture and stir them until they are well combined. Pour this thick and creamy filling over the bananas in your baking dish and spread it out evenly to the edges.

Step 6: The Final Topping

Place your second bag of cookies right on top of the pudding layer. I like to arrange them in neat rows so the chess designs are facing up. It makes the whole dish look so professional and beautiful.

Tips for the Best Paula Deen’s Chessmen Cookie Banana Pudding

Timing is everything with this recipe. You absolutely must chill the pudding for at least four hours before you even think about serving it. If you serve it too soon the cookies will be too hard and the pudding will not be set right. For the very best results I let it sit in the fridge overnight. This lets the cookies soften into a cake like texture. Also try to use bananas that are ripe but still firm. If they are overripe they will turn mushy and brown way too fast.

Estimated Nutritional Information

This dessert is a rich treat that I usually save for special occasions. Here is the estimated data per serving if you divide the dish into 12 helpings.

Calories 450 kcal
Total Fat 18g
Saturated Fat 11g
Cholesterol 35mg
Sodium 310mg
Total Carbohydrates 65g
Sugars 42g
Protein 6g

Frequently Asked Questions

Can I make Paula Deen’s Chessmen Cookie Banana Pudding ahead of time

Yes I actually recommend it. Making it 12 to 24 hours in advance gives those cookies time to absorb the moisture from the pudding which creates that signature texture everyone loves.

How do I keep the bananas from turning brown

The cream mixture actually helps seal the bananas away from the air and that slows down the browning. You can also toss your banana slices in a little bit of lemon juice or pineapple juice before you layer them to keep them looking fresh.

Can I use homemade whipped cream instead of whipped topping

You can use heavy cream whipped with a little sugar but just keep in mind that the pudding will be a little less stable. Real whipped cream tends to deflate faster than the store bought whipped topping does.

How should I store the leftovers

You should cover the dish tightly with plastic wrap or move the leftovers into an airtight container. Keep it in the refrigerator for up to three days. This recipe does not freeze well because the bananas and the dairy will change texture when they thaw out.