There are certain desserts you expect to see at a Southern gathering, and banana pudding is absolutely one of them. With Louisiana and Mississippi roots in my family, banana pudding is one of those desserts I don’t play about. After more than a decade sharing recipes online, I know the little details matter, especially when you’re making a classic people already have strong opinions about. This version keeps everything you love about old-school banana pudding while giving it a richer, buttery upgrade with those Chessman cookies.
Here's the Tea From Brandi
Banana pudding HAS to have cookies, period! I grew up with Southern desserts like banana pudding on the table, so I’m particular about what makes a good one. The pudding needs to be creamy, the bananas fresh, and the cookies need enough time to soften without completely disappearing into the filling.
You will also love my Biscoff Banana Pudding and classic desserts like Southern sweet potato pie, Southern peach cobbler, and sweet potato pie with graham cracker crust.
Chessman Banana Pudding Ingredients
- Vanilla Pudding
- Banana Cream Pudding
- Milk
- Sweetened Condensed Milk
- Vanilla Extract
- Chessman Butter Cookies
- Bananas
- For Homemade Whipped Cream: Heavy Whipping Cream and Powdered Sugar OR Cool Whip (if not making homemade whipped cream)
How to Make Southern Chessman Banana Pudding
Detailed measurements and full instructions can be found in the recipe card at the bottom of this post.
- Make the Pudding: Combine the vanilla and banana cream pudding with cold milk in a large mixing bowl. Beat the pudding mix and milk with a whisk for 2 minutes. Set aside for 5 minutes.
- Make the Sweetened Base: In a separate large mixing bowl, combine sweetened condensed milk, whipped cream or cool whip, and vanilla extract. Stir until combined.
- Fold in the Sweetened Whipped Cream with the Pudding: Next, add in the whipped cream mixture to the bowl with the pudding and fold. Fold the mixture, do not overmix. Use a rubber spatula or large spoon. Scoop down the side of the bowl, go under the mixture, then lift it up and over the top. Rotate the bowl slightly and repeat.
- Layer the Banana Pudding: Add a row of Chessman cookies to a 9x13 inch dish or dessert trifle. Add in ⅓rd of the sliced bananas. Drizzle ½ of the pudding mixture on top. Grab a handfull or two of Chessman cookies and crush them. Sprinkle crushed cookies throughout.
- Finalize and Decorate the Top: Add a final layer of pudding Add cookies on top to decorate the pudding.
- Chill: Chill for 2 hours to overnight.
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Southern Chessman Banana Pudding
Want to save this recipe for later?
I'll email it to you, so you can come back to it later! You will also grab your FREE ebook with my best 30-minute one-pot meals! Dinner stress stops here.
Ingredients
- 3.4 oz vanilla pudding I use standard vanilla.
- 3.4 oz banana cream pudding
- 2 cups cold milk I use whole milk. Other milk will work, but if it's thin it will change the texture of the pudding. It won't be as thick and creamy.
- 14 oz sweetened condensed milk
- 2 teaspoons vanilla extract
- 14.5 oz Chessman Butter Cookies This is two packs.
- 4 bananas Sliced into rounds
Homemade Whipped Cream (Use 8oz of Cool Whip if you don't want to make your own whipped cream.)
- 1 ½ cups heavy whipping cream
- 3 tablespoons powdered sugar
Instructions
Homemade Whipped Cream (Optional Use Cool Whip if you don't wish to make whipped cream)
- For the fluffiest whipped cream, place a large mixing bowl and the beaters or whisk attachment in the freezer for 10 to 15 minutes before you start.
- Pour the cold heavy whipping cream into the chilled bowl. Add the powdered sugar.3 tablespoons powdered sugar , 1 ½ cups heavy whipping cream
- Using a hand mixer or stand mixer, beat on medium speed for about 1 minute until the mixture starts to thicken. Increase to medium-high speed and continue beating for 2 to 4 minutes, until stiff peaks form. The whipped cream should hold its shape when you lift the beaters.
Banana Pudding
- Combine the vanilla and banana cream pudding with the cold milk in a large mixing bowl. Beat the pudding mix and milk with a whisk for 2 minutes. Set aside for 5 minutes.3.4 oz vanilla pudding , 3.4 oz banana cream pudding, 2 cups cold milk
- In a separate large mixing bowl, combine the sweetened condensed milk, whipped cream or cool whip, and vanilla extract. Stir until combined.14 oz sweetened condensed milk, 2 teaspoons vanilla extract
- Next, add in the whipped cream mixture to the bowl with the pudding and fold. Fold the mixture, do not overmix. Use a rubber spatula or large spoon. Scoop down the side of the bowl, go under the mixture, then lift it up and over the top. Rotate the bowl slightly and repeat. You’re turning the mixture over itself, not stirring it in circles.See notes for more information.
- Add a row of Chessman cookies to a 9x13 inch dish or dessert trifle. Add in ⅓rd of the sliced bananas. Drizzle ½ of the pudding mixture on top. Grab a handfull or two of Chessman cookies and crush them. Sprinkle crushed cookies throughout.14.5 oz Chessman Butter Cookies, 4 bananas
- Add a final layer of pudding Add cookies on top to decorate the pudding.
- Chill if preferred, 2 hours to overnight. After it's chilled I like to garnish it with more bananas and crumbled cookies.
Notes
Nutrition
Nutrition Data
Macros are provided as a courtesy and should not be construed as a guarantee. This information is calculated using MyFitnessPal.com. To obtain the most accurate nutritional information in a given recipe, you should calculate the nutritional information with the actual ingredients used in your recipe, using your preferred nutrition calculator. You are solely responsible for ensuring that any nutritional information provided is accurate, complete, and useful.
Frequently Asked Questions and Recipe Pro Tips
Chessman cookies are buttery shortbread-style cookies made by Pepperidge Farm. They’re a little richer and more buttery than traditional vanilla wafers, which is exactly why they work so well in banana pudding.
Use either one! I still love me some vanilla wafer banana pudding! It comes down to flavor and texture. Chessman cookies have that rich, buttery flavor that pairs perfectly with bananas and creamy pudding. Once everything chills together, the cookies soften and soak up some of the pudding without immediately turning to mush.
Yes! That’s part of the magic. The cookies start out crisp but soften as the pudding chills. Give the dessert several hours in the refrigerator and you’ll get that soft, almost cake-like texture.
I recommend at least 2 hours, but overnight is even better. Banana pudding is one of those desserts that needs a little time to do its thing. The flavors come together and the cookies have time to soften.
Absolutely, and I actually prefer it that way. Assemble it, cover it tightly, and refrigerate overnight. That gives you one less thing to worry about the day you plan to serve it.
Make sure the bananas are completely covered by the pudding as you assemble the layers. Limiting their exposure to air helps slow down browning. You can also lightly toss the slices with a little lemon juice, but don’t go overboard. Nobody wants lemon banana pudding.
Use ripe, yellow bananas that are firm with a few brown spots. You want them sweet, but not so ripe that they’re already soft and mushy. The heavily spotted bananas will work and are more sweet, just keep in mind they will be soft and mushy.
Start with bananas that aren’t overripe and make sure your pudding mixture is properly thickened before assembling. Extra moisture from overly soft bananas is usually where things start going left.
Of course. Vanilla wafers will give you that traditional Southern banana pudding flavor and texture. The Chessman cookies simply make it richer and more buttery.
Yes. Butter cookies, shortbread cookies, or vanilla wafers will work. Just keep in mind that changing the cookie will change both the flavor and how quickly it softens.
Layer the cookies, sliced bananas, and pudding so you get a little of everything in each scoop. I also like to finish with Chessman cookies on top because they make the pudding look good without doing a whole lot of extra work.
That’s usually the bananas oxidizing after being exposed to air. Some browning is completely normal, especially after the pudding has been stored for a couple of days. Keeping the bananas tucked between the pudding layers helps.
It’s best within about 2-3 days. The longer it sits, the softer the cookies and bananas will become. It may still taste good after that, but the texture won’t be at its best.
Now yall know I'm all about that freezing meals for later life, but not this one, friend. I don’t recommend it. The pudding can separate after thawing, and the bananas and cookies usually come back with a texture nobody asked for. This is definitely a make-it, refrigerate-it, and enjoy-it situation.
What to Serve with Banana Pudding
Soul food dishes will work great! Pair this with crispy fried chicken, Crockpot boneless turkey breast, Southern green beans and potatoes, collard greens with smoked turkey, and Southern mac and cheese.
More Dessert Recipes
Pumpkin Pie with Graham Cracker Crust
Pumpkin Pie with Frozen Crust
Pumpkin Cheesecake Dip
Sugar Free Cheesecake
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