Chessmen Cookie Banana Pudding

Chessmen Cookie Banana Pudding is a layered dessert recipe with butter cookies, fresh sliced bananas, and a creamy & thick banana cream pudding + french vanilla pudding mixture with cool whip, cream cheese, and sweetened condensed milk. If you love banana pudding then you have to try this! 

For more banana pudding dessert recipes be sure and try my No Bake Banana Pudding Cheesecake Pie, Banana Pudding Parfaits, and Banana Pudding Cookies. 

Chessmen Banana Pudding Recipe (Paula Deen Copycat Recipe)

If I was forced to pick my all-time favorite dessert, it would be banana pudding! Not just any banana pudding because I happen to love the ones that call for instant banana cream pudding. So yummy and easy to make. Which is why I love this Paula Dean copycat recipe for Chessmen Cookie Banana Pudding. 

It’s a layered dessert that starts with a layer of chessmen butter cookies, topped with fresh sliced bananas, then a creamy filling made up of instant pudding mixes (banana cream + french vanilla), cool whip, cream cheese, and sweetened condensed milk. And if that’s not enough, top it off with another layer of chessmen cookies!

I am not kidding when I say that you will LOVE this dessert. I have had this dessert at Paula Deen’s restaurant in North Carolina and although I don’t know what was in it, I can say that this recipe tastes spot on. I don’t normally crave sweet desserts but when I do, it’s this one ♥.

Ingredients You Need

Here is the list of ingredients that you will need to make this banana pudding layered dessert recipe. 

• Pepperidge Farm Chessmen Butter Cookies – This is not sponsored or anything but this brand is the only one that makes these Chessmen butter cookies. They’re like a shortbread + butter cookie in one and there really is no substitute for these cookies. 
• Bananas – You’ll need about 5 bananas for this recipe. For best taste be sure and use bananas that are yellow and ripe, not green as the taste will be a bit bitter. You also don’t want to use bananas that look like they’re ready for banana bread.
• Half & Half – For best results do not substitute this. Half and half is a lighter version of heavy cream and you want all that fat to help the banana pudding layer thicken and it makes it easier to cut.
• French Vanilla Instant Pudding – The combo of the French vanilla + banana cream is so good, but plain vanilla pudding works as well. 
• Banana Cream Instant Pudding – If you like the traditional recipe that calls for two vanilla instant pudding mixes then go ahead and do that. I prefer to have one vanilla + one banana cream as it brings out that banana pudding flavor better. 
• Cream Cheese – You can use regular fat cream cheese or reduced-fat cream cheese. Either will work great in this recipe. I prefer the taste and texture of the full-fat cream cheese so that is what I use. 
• Sweetened Condensed Milk
• Cool Whip

How To Make Banana Pudding with Chessmen Butter Cookies and Pudding

Learn how to make banana pudding at home with this no bake, simple step recipe that uses Chessmen butter cookies, instant pudding, cool whip, and sweetened condensed milk. 

• Step One : Take one package of the butter cookies and layer them in the bottom of a 9×13 baking dish. I like to open both packs of cookies and use any broken ones up on the bottom layer, because you won’t be able to see them anyways. 
• Step Two : Slice the bananas into thin slices and layer them over top the cookie layer. You may have to double up the layer of bananas which is fine. 
• Step Three : In a mixing bowl, mix together the half and half milk + the instant pudding mixes and stir with a whisk until it’s thick and combined. Let this sit for 5 minutes while you prepare the rest.
• Step Four : In a separate bowl, beat together the cream cheese and sweetened condensed milk until combined well. Fold in the thawed cool whip and stir. Add the thickened pudding mixture into the cream cheese mix and stir. Spread this layer over the banana slices. 
• Step Five : Take the second bag of cookies and make a cookie layer on top. Be sure and do the same pattern as you did on the bottom layer so you can cut the dessert into nice slices. 
• Step Six : Cover the pan with plastic wrap and let it refrigerate for at least 6 hours before cutting and serving. Even longer is fine too! Read below for all my tips on preparing it ahead of time. 

Tips For Success

Here are a few of my helpful tips so that you too can have success with this recipe in your own kitchen!

• Plan Ahead : Do not try to rush this dessert before serving. It won’t work! Once you make this banana pudding, it needs to refrigerate for at least 6-8 hours before cutting and serving it. It needs the fridge time so the layers can set together, the cookies can soften somewhat, and for the banana flavor to infuse all the layers. 
• Chessmen Cookies : These are more expensive but it will be worth it. There really are no substitutes besides Nilla wafers but then that would be a whole different dessert. The chessmen butter cookies are so good in this recipe!
• Use Half and Half : I do not recommend substituting this with anything else. You need that fat to help the pudding layer set and thicken up nicely. 
• Cookie Layers : Make sure that you do the cookies in the same pattern for the bottom layer and top layer. This way, you can use the cookies as the cutting guide for each serving. So if you do 4 columns with 6 cookies in each columns (24 total) do that exact same pattern on the top layer. If you have to cut some cookies in half, that’s fine, just make sure you do the same pattern for the top layer of cookies. 

Chessmen Banana Pudding FAQ’s

• Can I Make It Ahead of Time?
  • Yes! This recipe needs at least 6-8 hours of chill time in the fridge before you cut it and serve it. 
  • You can even make it the day before and let it refrigerate overnight. I actually prefer the texture of the cookies when it has refrigerated for at least 12 hours before serving it. But it’s totally up to you depending on how soft or slightly crunchy still you want the cookies to be. 
  • Because the banana layer is not exposed, you can make it the day before and let it refrigerate until ready to serve, without worrying that the bananas will brown. 
• How To Store Leftover Chessmen Cookie Banana Pudding
  • Leftovers will store in the fridge, covered, for up to 4-5 days. The longer it sits in the fridge, the softer the cookies will become. But trust me, not even the soft cookies stopped us from eating leftovers on day 5. So good!
  • If the banana layer is exposed then it will turn brown. You can either eat it because it still tastes good or just get one of the pieces where the edges have not gotten exposed yet. 
  • I leave the banana pudding dessert in the same baking pan I made it in to store leftovers. That way, some of the pieces are still not exposed yet which means the bananas won’t turn brown. 
  • My husband came into the kitchen plenty of times to see me taking a fork and just digging right into the pan of leftovers from the fridge!
• Variation & Substitution Ideas
  • Although I highly recommend making the recipe as is, there are a few ways to switch it up if wanted. 
  • Pudding : I love the combo of French vanilla + banana cream but you can also do 2 banana cream puddings for extra banana flavor, or try using plain vanilla + banana cream, or use 2 vanilla puddings. I do recommend using at least one box of banana cream because it makes this taste amazing and makes that banana flavor more intense. 
  • Chessmen Cookies : This recipe is called ‘chessmen cookie’ after all, but if wanted you can use Nilla wafers instead. I don’t recommend it in this recipe because once you have banana pudding with chessmen cookies, you’ll never want it any other way again. 

More Banana Dessert Recipes You’ll Love

• Cinnamon Banana Bread Muffins
• Lemon Blueberry Banana Bread
• Buttermilk Banana Bread
• Chocolate Chip Banana Bars
• Chocolate Chip Banana Muffins
• Peanut Butter Chocolate Chip Banana Bread
• Banana Pumpkin Bread
• Banana Pudding Fluff Salad