This Chessmen Banana Pudding is one of those desserts that never fails to impress. It’s creamy, dreamy, and layered with buttery Pepperidge Farm Chessmen cookies that add the perfect crunch. The vanilla pudding blends smoothly with bananas and cream cheese for a dessert that’s both simple and show-stopping.

If you’re a fan of classic banana pudding recipes, this rich version will make you fall in love all over again.
Ingredients
- 2 packages (7.25 oz each) Pepperidge Farm Chessmen cookies
- 6 to 8 ripe bananas, sliced
- 1 (5 oz) box instant vanilla pudding mix
- 2 cups cold milk
- 1 (8 oz) package cream cheese, softened
- 1 (14 oz) can sweetened condensed milk
- 1 (12 oz) container whipped topping (Cool Whip), thawed
- 1 teaspoon vanilla extract
- Pinch of salt
Instructions

- In a large mixing bowl, beat the softened cream cheese until smooth and fluffy.
- Add the sweetened condensed milk and vanilla extract, mixing until combined.
- In another bowl, whisk together the instant pudding mix and cold milk until thick, about 2 minutes.
- Fold the pudding mixture into the cream cheese mixture until smooth and creamy.
- Gently fold in the whipped topping, being careful not to deflate the mixture.
- Line the bottom of a 9×13 inch dish with one layer of Chessmen cookies.
- Add an even layer of banana slices over the cookies.
- Pour half of the pudding mixture over the bananas, spreading evenly with a spatula.
- Repeat the layering: another round of cookies, bananas, and the remaining pudding mixture.
- Top with the final layer of Chessmen cookies. Press them gently so they set into the pudding slightly.
- Cover and refrigerate for at least 4 hours, or overnight for best results.
- Before serving, chill until firm and slice into squares. The top cookies will soften slightly, giving the pudding a lovely cake-like texture.
Why You’ll Love This Recipe

This Homemade Banana Pudding With Cream Cheese has a light, mousse-like texture and the sweet crunch of cookies. It’s one of the Recipes That Use Banana Pudding in the most comforting way. Each bite feels like a hug in dessert form. Plus, there’s no baking involved, making it one of the easiest Desserts Using Bananas Easy Recipes for any gathering or cozy night at home.
Tips for the Perfect Chessmen Banana Pudding

- Bananas: Use ripe bananas with light brown spots for the best flavor. Avoid overripe or blackened ones if you don’t like strong banana taste.
- Layering: Make sure your bottom layer of cookies covers the dish completely. This helps the pudding set properly.
- Chilling Time: Don’t skip the chill! The longer it sits, the better the flavors meld together.
- Variation: For a lighter version, swap regular pudding for a Light Banana Pudding mix and use low-fat cream cheese.
- Personal Touch: Make Personal Banana Pudding cups by layering ingredients in small mason jars for parties or picnics.
Serving Ideas
This pudding shines as a summer dessert or potluck favorite. Serve it with a drizzle of caramel sauce or crushed cookies for extra crunch. If you enjoy trying new banana pudding twists, explore this Magnolia Bakery Banana Pudding for another famous version, or check out this Strawberry Banana Cream Pudding for a fruity mix-up. This creamy dessert is right up there with the Best Banana Pudding Recipe From Scratch when it comes to texture and flavor.

Chessmen Banana Pudding
Ingredients
Equipment
Method
- In a large mixing bowl, beat the softened cream cheese until smooth and fluffy.
- Add the sweetened condensed milk and vanilla extract, mixing until combined.
- In another bowl, whisk together the instant pudding mix and cold milk until thick, about 2 minutes.
- Fold the pudding mixture into the cream cheese mixture until smooth and creamy.
- Gently fold in the whipped topping, being careful not to deflate the mixture.
- Line the bottom of a 9×13 inch dish with one layer of Chessmen cookies.
- Add an even layer of banana slices over the cookies.
- Pour half of the pudding mixture over the bananas, spreading evenly with a spatula.
- Repeat the layering: another round of cookies, bananas, and the remaining pudding mixture.
- Top with the final layer of Chessmen cookies. Press them gently so they set into the pudding slightly.
- Cover and refrigerate for at least 4 hours, or overnight for best results.
- Before serving, chill until firm and slice into squares. The top cookies will soften slightly, giving the pudding a lovely cake-like texture.
Notes
- Use ripe but firm bananas for best results.
- For added flavor, consider a drizzle of caramel sauce or a sprinkle of crushed cookies on top.
- This dessert improves with time, overnight chilling gives the best texture.
Common Questions (FAQs)
1. Can I make Chessmen Banana Pudding ahead of time?
Yes! It actually tastes better the next day because the cookies soften and the flavors blend together beautifully. Just cover it tightly with plastic wrap and keep refrigerated.
2. My pudding turned too runny. What went wrong?
This can happen if the pudding wasn’t whisked long enough or if it was made with warm milk. Use cold milk and whisk for at least 2 minutes until it thickens before combining with the cream cheese mixture.
3. Can I use other cookies instead of Chessmen?
Absolutely. While the Chessmen give a lovely buttery taste, you can use vanilla wafers or shortbread cookies. Just know that the flavor and texture will be slightly different, similar to Chess Banana Pudding versions made with wafers.
Conclusion
There’s something timeless about this Chess Men Banana Pudding. Creamy pudding, soft bananas, and buttery cookies create a dessert that feels like comfort in every bite. It’s perfect for family gatherings, holidays, or anytime you crave a nostalgic treat. Save or pin this recipe so you’ll always have it handy for those moments when you want something sweet, simple, and irresistible.
