Simple Chessman Banana Pudding

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Chessman cookies are butter shortbread cookies that come in a nice little bag and go amazing with coffee or tea. My father used to get them for himself as a self-care gift, so I thought they must be super expensive and fancy cookies. That’s why this chessman banana pudding feels and tastes so lush. If you crave a little chocolate with it, make this chocolate banana pudding instead. 

This recipe is incredibly quick and easy to whip together and the only cooking is for the pudding on the stovetop (though read below for a hack to get out of that).

However, the vanilla pudding and the assembled chessman banana pudding both need several hours to set in the fridge. Because of that, it is best to prepare the vanilla pudding the day before and make the dessert before dinner to allow it to rest in the fridge until you are ready for it later in the evening. It can also be prepared the day before and left in the fridge overnight, though as noted below, the cookies will become softer.

Chessman Banana Pudding

Prep Time: 35 minutes
Cook Time: 14 minutes
Chill Time: 6 hours
Total Time: 6 hours 49 minutes
Servings: 15
Calories: 698kcal


  • 2 eggs
  • 1/3 cup sugar
  • 3 tbsp cornstarch
  • Pinch of salt
  • 2 ¼ cups milk
  • 1 ½ tbsp butter
  • 2 tsp vanilla
  • 2 cups heavy whipping cream
  • 1 cup powdered sugar
  • 1 ½ tsp vanilla
  • ¼ tsp salt
  • 2 packets chessman cookies
  • 8 bananas
  • 8 oz cream cheese
  • 1 can sweetened condensed milk


  • Set the cream cheese out so it can soften to room temperature. Separate the egg yolks from the whites and put the whites aside or discard.
  • Put the egg yolks into a small pot over medium-low heat along with the sugar, cornstarch, salt, and milk. Whisk well to incorporate.
  • Leave the pot over medium-low heat for about 10 minutes or until it starts to bubble. Stir occasionally with a rubber spatula to help it cook evenly and avoid sticking to the bottom of the pot.
  • When the mixture begins to bubble, leave on heat for another two minutes, stirring slowly with the spatula. The texture should be very thick, but not stiff.
  • Remove from heat and pour in the vanilla. Add the butter and stir slowly with the spatula until the vanilla is incorporated and the butter has melted.
  • Place a sieve over a clean bowl and pour the pudding through the sieve. You can use the spatula to help push the pudding through. This helps eliminate any lumps and helps the pudding cool evenly.
  • Press plastic wrap into the bowl to rest just on top of the pudding. This is to prevent a skin from forming on top. Put the pudding into the fridge and let set for three hours or until fully chilled and thickened.
  • To make the whipped cream, add the heavy whipping cream to the bowl of a stand mixer. You can also use an electric, hand-held whisk or even a regular whisk, but if you do it manually it will take a lot longer and make your arms tired.
  • Add the powdered sugar, salt, and vanilla. Use the whisk attachment and whisk at medium-high speed for about 5 minutes or until stiff peaks form.
  • If using a stand mixer, transfer the whipped cream to another bowl (you will need to use the mixer bowl again). Put the whipped cream in the fridge.
  • In the bowl of a stand mixer (or again, use a handheld electric mixer or your arms) add the cream cheese and can of sweetened condensed milk. Use the paddle attachment and beat the cream cheese and condensed milk until thick and smooth. Use a spatula to scrape down the sides of the bowl as needed. Add the previously made vanilla pudding to the bowl and gently beat to incorporate. Remove the bowl from the mixer and add the whipped cream. Use a spatula to gently fold in.
  • Peel and slice all the bananas.
  • To assemble the chessman banana pudding, get a 9×13 inch baking dish. Put 1 layer of chessman cookies on the bottom (this should equal one bag).
  • Scoop some of the pudding mixture over the cookies and use a spatula to spread it into a thin layer.
  • Place the banana slices on top as evenly as possible.
  • Dump the rest of the pudding on top and spread out evenly.
  • Finish off by placing the remaining cookies in a layer on top and just barely pressing down on them so they stick to the pudding.
  • Cover and place in the fridge for 3 hours to allow the pudding to firm up and chill through.
  • Spoon into bowls and enjoy!



Calories: 698kcal | Carbohydrates: 85g | Protein: 10g | Fat: 37g | Saturated Fat: 18g | Polyunsaturated Fat: 6g | Monounsaturated Fat: 9g | Trans Fat: 0.002g | Cholesterol: 86mg | Sodium: 365mg | Potassium: 493mg | Fiber: 2g | Sugar: 51g | Vitamin A: 925IU | Vitamin C: 6mg | Calcium: 172mg | Iron: 2mg

Notes & Tips

You can use any type of butter cookie for this recipe. This dish can be kept covered in the fridge for 5 days. Bear in mind that the longer the pudding sits, the softer the cookies will get. This is not a bad thing, softer pudding tastes just as good! But be aware if you are considering making this a few days in advance.


If you do not want to go through the process of making your own vanilla pudding, you can use 1 packet of instant vanilla pudding instead. Just follow the instructions on the packet. If you really love the banana flavor, you could even use a banana pudding instead of vanilla. 

Similar to the pudding hack, you can replace the homemade whipped cream with store bought. If you do, it is best to buy one like cool-whip that comes in a big tub instead of the spray cream in cans.

The main feature of this dessert is the chessman cookies. They’re yummy and have fun patterns to decorate the top of the pudding. However, chessman cookies can be a little more expensive than other cookies such as nilla wafers or off-brand shortbread. If you want to make this recipe a tad more budget friendly, you can cut out the chessman cookies and use nilla wafers, shortbread cookies, or a similar off-brand substitute. 

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