Creamy, sweet, and full of rich banana flavor, this Banana Pudding with Chessman Cookies is a true Southern classic with a twist. Made with layers of crisp Chessman cookies, homemade banana-infused pudding, and a velvety cream cheese layer. It takes just minutes to prepare before chilling lets the flavors meld, creating a dessert that’s smooth, sweet, and packed with banana flavor.
Banana Pudding with Cream Cheese and Condensed Milk
There’s nothing more Southern than a big dish of banana pudding, and this version takes it to the next level. You can forget about instant pudding mix or cool whip for this recipe. With layers of homemade banana pudding, fresh bananas, and a rich, cheesecake-like cream cheese filling, every bite is as creamy and comforting as the last.
Unlike traditional banana pudding, which relies on vanilla pudding and sliced bananas for flavor, this recipe blends bananas right into the pudding itself, giving it an even deeper banana flavor. Cream cheese adds a tangy flavor and richer texture, giving this homemade banana pudding recipe a more indulgent feel.
Chessman cookies take the place of the usual vanilla wafers, adding a buttery flavor and crispier texture that holds up beautifully. Plus, they make for an eye-catching presentation when lined up on top.
This dessert is a staple at Sunday suppers, backyard barbecues, and potlucks. Since Chessman cookies are a little thicker and crispier than vanilla wafers, you can make this in advance and the cookies will maintain their shape longer than vanilla wafers.
Since it’s such a rich dessert, it’s a great dessert to serve with bbq chicken or slow cooker ribs.
Why You’ll Want to Make This Again and Again
- No tempering eggs: With this method the eggs are cooked with the milk, not tempering needed.
- Extra banana flavor: Unlike regular banana pudding, this one has bananas mixed into the pudding, not just sliced on top.
- Creamy and rich: The cream cheese layer adds a little tang and makes the pudding extra thick and velvety.
- Buttery chessman cookies: Instead of vanilla wafers, this recipe uses Chessman cookies, adding a buttery, melt-in-your-mouth texture.
Chessman Banana Pudding Uses Simple Ingredients
These are the main ingredients you’ll want to get for this recipe. Make sure to check the recipe card for the full list of ingredients.
- Bananas: Use ripe but firm bananas for the best balance of sweetness and texture.
- Cream cheese: Gives the pudding a slightly tangy, cheesecake-like flavor and makes it extra thick and luscious.
- Sweetened condensed milk: Adds a smooth, caramel-like sweetness and helps create that ultra-creamy consistency.
- Chessman cookies: Buttery, crisp, and slightly sweet, these cookies hold up beautifully against the creamy layers and add the perfect crunch. This recipe uses Pepperidge Farm Chessmen Cookies, but shortbread cookies or regular butter cookies would also work, or of course you could use vanilla wafers.
A Foolproof Method for Creamy Banana Pudding with Chessman Cookies
Step One: Make the Pudding
Step Two: Mix the Cream Cheese Layer
Pro tip: Make sure the cream cheese is at room temperature before beating so it’s easy to blend and there are no lumps. If you forget to let it sit out, you can soften cream cheese quickly.
Step Three: Whip the Cream
Step Four: Assemble the Layers
Step Five: Chill and Serve
Refrigerate for a few hours until set, then grab a spoon and dig in!
Storing and Making Banana Pudding Ahead of Time Is Easy
- Store: Cover the banana pudding tightly with plastic wrap or a lid and pop it in the refrigerator for up to 2 days. After a day or two the bananas will brown, the cookies will soften and the cream will flatten. This is dessert that should be eaten within a day for best results.
- Make Ahead: This is the perfect make-ahead dessert since it needs several hours to chill and set. You can prepare it the night before and let it sit in the fridge overnight. If you want the Chessman cookies on top to stay crisp, wait to add them until just before serving.
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Ingredients
Pudding
- 4 tablespoons sugar
- 2 tablespoon cornstarch
- ½ teaspoon salt
- 2 eggs
- 1 ½ cup whole milk
- 2 tablespoons butter
- 1 teaspoon vanilla
- 1 cup chopped banana
Cream Cheese Layer
- 8 ounces cream cheese
- ¾ cup sweetened condensed milk not an entire 14 oz can
- 1 ½ cups heavy cream
- 1 tablespoon cornstarch
- 5 bananas thinly sliced
- 2 bags Chessman Cookies
Instructions
- In a medium saucepan, add sugar, 2 tablespoons cornstarch and salt. Whisk in milk and eggs. Bring to a boil over medium high heat, whisking constantly for about 5 minutes. It should be very thick. Remove from the heat and add butter and vanilla, whisk until combined and place in a large bowl in the refrigerator.
- In a medium bowl, whisk together the cream cheese and sweetened condensed milk until smooth. Stir in a cup of chopped bananas. Fold this into the warm, not hot, pudding mixture and refrigerate for at least an hour.
- Beat the heavy cream with 1 tablespoon of cornstarch until very stiff peaks form. Fold it into the cold pudding.
- Add 12 chessman cookies to the bottom of a 9 x 13 inch baking dish. Top with sliced bananas. Spoon the pudding mixture over the top and even off the top. Add a layer of Chessman cookies to the top. Refrigerate for 4-6 hours before serving.
Notes
- You can use vanilla wafers instead of Chessman cookies
- This is best served within 1 day.
