This Chessman banana pudding is the dessert that disappears fastest at every potluck I bring it to. Those buttery cookies soften into something almost like cake as it chills, layered with sweet bananas and creamy vanilla pudding. Best of all, it’s no-bake, so I can make it the night before!
More easy, make-ahead desserts:
Before You Get Started
Keep these tips in mind for a perfect pan of banana pudding:
- Let the pudding soft-set first. Whisk it with cold milk and chill a few minutes before layering, or the layers will slide.
- Use ripe bananas, sliced last. They should be a nice yellow color (and can be speckled and very ripe, if you like them really sweet). Slicing right before you layer keeps them from browning.
- Don’t rush the chill. It needs at least 4 hours, ideally overnight, for the cookies to soften into that cake-like texture.
How to Make Chessman Banana Pudding
This easy dessert comes together in just a few simple layers. Most of the work is waiting for it to chill in the refrigerator!
Step 1: Make the Pudding
In a large bowl, whisk the vanilla instant pudding mix and cold milk together for about 2 minutes, until the mixture begins to thicken. Whole milk creates the richest, creamiest texture, but any milk that works with instant pudding will do the job.
For a deeper vanilla flavor, you can substitute French vanilla instant pudding.
Refrigerate the pudding for about 5 minutes while you prepare the remaining ingredients.
⇢ For a richer, more traditional pudding: Many folks know banana pudding as the Paula Deen “Not Yo Mama’s” style. To get there, beat 1 (8-ounce) block of softened cream cheese and 1 (14-ounce) can of sweetened condensed milk into the prepared pudding. Then fold in a tub of Cool Whip. The result is richer, denser, and extra indulgent.
Step 2: Start Your First Layer
Arrange a single layer of Chessmen cookies across the bottom of a deep 9 x 13-inch dish, using about 20 cookies (or as many as fit snugly). You can break the cookies, if needed, to fit in the bottom of your dish.
Those buttery, shortbread-like cookies are what make this version special. If needed, you can substitute Nilla Wafers for a more traditional Southern banana pudding, plain shortbread cookies for a similar flavor, or Biscoff cookies for a lightly spiced twist.
⇢ A deeper baking dish works best because it gives you room for generous layers.
Step 3: Add Bananas and Pudding
Arrange half of the banana slices in an even layer over the cookies.
Spoon half of the soft-set pudding over the bananas and spread it gently to cover.
Step 4: Repeat, Then Chill
Add another layer of cookies, followed by the remaining banana slices and the remaining pudding. Spread the whipped topping evenly over the top, then finish with a final layer of Chessmen cookies.
Cover tightly and refrigerate for at least 4 hours or overnight before serving.
Storage, Freezing & Make-Ahead
Make-ahead: This is a make-ahead dream. Assemble it up to a day in advance and let it chill overnight. It actually tastes better after a long rest in the fridge, which makes it perfect for potluck spreads and cookouts you’re prepping for.
Storage: Keep it covered in the fridge for up to 2 to 3 days. The bananas will soften and darken a bit over time and the cookies keep getting softer, so it’s at its prettiest in the first day or two.
Freezing: Not recommended. The bananas and whipped topping don’t hold up well to freezing and thawing, so this one is best enjoyed fresh from the fridge.
Frequently Asked Questions
My cookies softened. Is that supposed to happen?
Yes! That’s exactly what you’re looking for. As the pudding chills, the Chessmen cookies absorb moisture and become soft and cake-like. That’s one of the signature characteristics of a great banana pudding.
How do I keep the bananas from turning brown?
Slice the bananas right before layering and use ripe but still firm fruit. If you’re preparing the dessert well ahead of time, you can lightly toss the slices with a small amount of lemon juice or pineapple juice to help preserve their color.
Can I make it in a trifle bowl or individual cups instead?
Absolutely. A clear trifle bowl creates a beautiful presentation and shows off all of the layers. Individual dessert cups or mason jars are also great options for parties and easy serving.
Can I use homemade pudding instead of instant pudding?
Yes. Homemade vanilla pudding works beautifully if you have the extra time. Just make sure it has cooled completely before layering.
More Easy No-Bake Desserts
Watch How to Make It
Chessman Banana Pudding
Equipment
- 9 x 13 inch dish
Ingredients
- 2 (3.4 ounce) packages vanilla instant pudding mix
- 4 cups cold milk
- 3 (7.25 ounce) packages Pepperidge Farm Chessmen butter cookies
- 4 large ripe bananas, sliced
- 2 (8 ounce) cartons frozen whipped topping (such as Cool Whip), thawed
Instructions
- Beat the milk and pudding mix in a large bowl with a whisk for 2 minutes, according to package directions. Refrigerate until soft set and ready to use.
- Arrange 20 cookies (or as many as fit) in a single layer in the bottom of a deep 9 x 13-inch dish.
- Arrange half of the banana slices in a single layer on top of the cookies.
- Spread half of the pudding mixture over the bananas.
- Top with another layer of 20 cookies, the remaining banana slices, and the remaining pudding mixture.
- Add a layer of whipped topping, and then evenly arrange a final layer of 20 cookies on top. Cover and refrigerate for at least 4 hours (or overnight).
Notes
- Soft-set first: Let the whisked pudding chill for a few minutes before layering, so the layers hold their shape and don’t slide.
- Banana tip: Use ripe but firm bananas and slice them just before layering to limit browning.
- Cookie swaps: Nilla wafers or shortbread work well in place of Chessmen, and Biscoff adds a warm, spiced note.
- French vanilla: Swap in French vanilla instant pudding for a deeper flavor.
- Richer version: For the classic Paula Deen style, beat 1 (8-ounce) block of softened cream cheese and 1 (14-ounce) can of sweetened condensed milk into the prepared pudding. Then fold in a tub of Cool Whip.
- Make ahead and store: Best assembled a day ahead, since the flavor and texture improve overnight. Keep covered in the fridge for up to 2 to 3 days.
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