Chessmen Banana Pudding Recipe: Rich, Creamy & Perfect for the Holidays

If you love banana pudding like I do, especially doing the holidays then you must try my Chessmen Banana Pudding recipe. My traditional banana pudding that I have been making for decades is a classic, but this banana pudding made with Chessmen cookies has up my the banana pudding game. The texture of the cookies are cake-like and the pudding is rich and creamy. Add it to your holiday dessert table along with peach cobbler and sweet potato pie and I promise your family will thank you for it.

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If you love bananas, try my classic banana pudding recipe and my banana cream pie recipe.

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Why you’ll love this recipe:

• Elevated twist on a classic: Chessmen cookies add a rich, buttery flavor that takes traditional banana pudding made with Nilla wafers to the next level.
• Rich and creamy texture: Homemade custard is smooth, velvety and perfectly balanced. Not too sweet.
• Perfect for holidays and gatherings: This dessert feels nostalgic yet special, making it ideal for Thanksgiving, Christmas and your family dinners.
• Make-ahead friendly: It tastes even better once chilled, so making it ahead of time saves you time.
• A guaranteed crowd-pleaser: If your family already loves banana pudding (like I do), making Chessmen Banana Pudding will definitely please the crowd.

Ingredients

• Bananas: Ripe, fresh bananas gives the pudding natural sweetness and flavor.
• Chessmen Cookies: Buttery shortbread cookies that elevate the overall taste of this dessert.
• All-Purpose Flour: Thickens the pudding and gives it a smooth consistency.
• Milk: Help create the base of the pudding an gives it a creamy and balance.
• Butter: Adds richness and depth of flavor to the custard.
• Heavy Cream: Enhances creaminess and gives the pudding its luxurious texture.
• Egg Yolks: Provide structure and richness to the custard.
• Sugar: Sweetens the pudding while balancing the flavors.
• Vanilla Extract: Adds warmth and classic dessert flavor that ties everything together.
• Almond Extract: A subtle flavor enhancer that complements the cookies and custard without overpowering.
• Salt: Enhances sweetness and balances the richness of the pudding.

Substitutions and Variations

• Cookies: If Chessmen cookies are not available you can use any other comparable brand of shortbread cookies, the traditional vanilla wafers or butter cookies. Keep in mind the overall flavor may be slightly different.
• Milk: Whole milk works best, but you may substitute 2% if needed.
• Almond extract: This is optional and can be omitted if you prefer a classic vanilla only flavor.
• Bananas: Use firm, ripe bananas to prevent mushiness and to maintain clean layers.
• Pudding shortcut: You can use a high-quality vanilla pudding mix, but homemade pudding will give you the best flavor.

What You Will Need

• Stand Mixer/ Hand Mixer
• Cooking Utensils
• Baking Dish

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Instructions

Step 1: Make the Whipped Cream

To make the whipped cream, use and hand or stand mixer with a chilled bowl and whisk the heavy cream until stiff peaks form. After you are done, set the bowl in the refrigerator until needed. Store bought whipped cream can be used if you prefer.

Step 2: Prepare the Custard

Heat a medium pot over medium heat and add the milk and egg yolks. Whisk until well combined. Stir in the sugar, salt, and flour, mixing until the ingredients are fully incorporated.

Continue stirring constantly, allowing the mixture to simmer until it thickens into a custard-like consistency. Once thickened, remove from heat and add the butter, vanilla extract, and almond extract. Mix well. Allow the custard to cool for 5 minutes. After cooling, fold in 1 cup of whipped cream, gently mixing until smooth.

Step 3: Assemble the Banana Pudding

In a serving dish, layer the Chessmen cookies as the base.

Add a layer of sliced bananas, followed by a layer of pudding. Repeat the layers until all ingredients are used, ending with a layer of pudding on top.

Step 4: Chill and Serve

Serve chilled and enjoy this creamy, delicious Chessmen Banana Pudding! Cover and refrigerate for at least 4 hours to allow the flavors to meld.

Serving Suggestions

Classic family-style: This pudding is best served chilled. You can simple place it in a baking dish and layer it as I did, or be a little more creative and use a large glass trifle dish to show off the beautiful layers of bananas, custard, and Chessmen cookies.

Individual dessert cups: This way is ideal for holidays, parties or portion control. Dessert cups travel well when you need to make this pudding for the office potluck.

Holiday buffet favorite: There are endless options but I love to pair banana pudding with other classic desserts like pound cake, sweet potato pie, or peach cobbler for a Southern-inspired dessert table.

Topped and dressed up: If you want more than the layered cookie appearence, it’s perfectly ok to change things up. Garnish with whipped cream, crushed Chessmen cookies, banana slices, or a light dusting of vanilla wafer crumbs.

Make-ahead dessert: Make this the night before and serve straight from the refrigerator. No reheating needed.

FAQ

Chessmen Banana Pudding is a decadent dessert that is rich and creamy. A great twist to classic banana pudding that you can try when you want something extra special. Enjoy it during the holidays or all year round, there is never not a good time for this delicious dessert.