Chessman Cookie Banana Pudding

This Chessman Cookie Banana Pudding is a twist on the classic Southern banana pudding. It’s a no-bake dessert, that’s best to make in advance and can serve quite the crowd! With layers of creamy pudding, buttery shortbread cookies, and ripe bananas, it’s a treat that will be gone in minutes at any family gathering.

Calling all of my banana pudding lovers, this Chessman Cookie Banana Pudding will be your new favorite dessert! It’s a twist on my family’s famous banana pudding, using the classic store-bought shortbread cookies as well as a cream cheese whipped cream filling that is so so decadent.

Layered with ripe bananas and refrigerated until every bite melts in your mouth, this banana pudding with chessman cookies will be a dessert that will be requested by friends and family for years and years to come. If you love a Southern dessert, be sure to also try my Coconut Pound Cake or Lemon Delight.

Why You’ll love this recipe

• No-bake dessert that’s easy for anyone to make. If you’ve never made banana pudding before, it’s super simple! Even my kids like to help me layer the dessert.
• Serves a large crowd. It’s the best sweet treat for potlucks, church picnics, holidays, and more. Plus, it transports well too.
• Make ahead magic. I like to assemble the pudding the night before to make sure it’s the correct texture when it’s time to eat.

ingredients

Scroll Down for Ingredient Amounts Listed in the Printable Recipe Card Below

Pudding Base

• Instant French vanilla pudding mix: Adds rich vanilla flavor to every bite and responsible for that creamy texture.
• Evaporated milk: One of my secret ingredients, make sure it’s chilled for easier whipping. This adds a rich milk flavor to every bite.
• Sweetened condensed milk: Adds a hint of sweetness and even more creaminess to the chessman banana pudding.

Cream Cheese Whip Layer

• Cream cheese: You’ll want to soften this in advance for easy mixing. Adds a richness with a hint of cheesecake flavor.
• Vanilla extract or paste: Perfect addition for both caramel and floral flavors that will make it irresistible!
• Powdered sugar: Sweetens the cream cheese whip layer perfectly.
• Heavy whipping cream: Make sure this ingredient is chilled, it helps the filling hold it shape and gives it a light, airy quality.

Layers

• Chessmen Butter cookies: The buttery, shortbread cookie that compliments the sweet pudding so nicely.
• Ripe bananas: Make sure your bananas are nice and ripe; they add more natural sweetness to the pudding.
• Garnish options: fresh mint, dehydrated banana slices, fresh banana slices, fresh whipped cream are all my favorite options when it comes to finishing this dessert off with a pretty touch.

Tools You’ll Need

• Spatula
• Mixing Bowls
• Hand Mixer 
• Measuring Cups and Spoons
• Liquid Measuring Cups
• 13”x9” Baking Pan

how to make chessman cookie banana pudding

1. In a medium bowl, with a hand mixer mix together the pudding mix and chilled evaporated milk for about 2 minutes, until thickened. Mix in the sweetened condensed milk until smooth. Cover and refrigerate while you prepare the cream layer.

2. In another bowl with a hand mixer, beat the cream cheese until completely smooth.
3. Add powdered sugar and vanilla extract. Beat again until smooth.
4. With the mixer running on medium speed, slowly pour in heavy whipping cream. Once the mixture begins to thicken, whip on high speed until stiff peaks form.

5. Gently fold the chilled pudding mixture into the cream cheese whipped cream until fully combined.

6. Add an even layer of Chessmen cookies in the bottom of a 13×9-inch baking dish.
7. Top with an even layer of sliced bananas.

8. Spread evenly half of the pudding mixture, add another layer of bananas, then spread on the rest of the pudding mixture in an even layer.

9. Top with whole or crushed Chessmen cookies.

10. Refrigerate at least 4 hours before serving. Garnish as desired.

expert tips

• Make sure your evaporated milk is cold. This helps with whipping the pudding mix to the correct consistency for that delicious texture.
• When folding the pudding and cream cheese whipped cream together, don’t stir quickly. Slow folding is best and don’t over-mix or you will deflate the whipped cream!
• Give the chessman banana pudding the right amount of time to set. At least 4 hours is key to allow the cookies to soften and become tender in each bite.
• Add other fruit if desired. I’ve also added berries like sliced strawberries, blackberries, or blueberries to this banana pudding for a fun twist on the flavors.
• Opt for a different cookie. You can also make this with vanilla wafers, shortbread cookies, sugar cookies, graham crackers, or Biscoff cookies.

storage

Store any leftover banana pudding with chessman cookies in an airtight container in the fridge for up to 3 days. I don’t recommend freezing the dessert as it will change the texture once thawed.

Frequently Asked Questions

more southern dessert recipes

• Baked Banana Pudding
• Chocolate Meringue Pie
• Coconut Layer Lush
• White Texas Sheet Cake