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Easy Cream Cheese Banana Pudding w/Chessmen Cookies

Make the best banana pudding with Chessmen cookies recipe (cream cheese, pudding, bananas, cookies). Firm no-bake dessert always holds its shape.

Cream cheese banana pudding with Chessmen cookies

Chess fans (and everyone else) will love this banana pudding with Chessmen cookies recipe. A creative twist on a traditional banana pudding, it has the same delicious flavor with a fun and impressive presentation.

Forget the classic recipe. This delicious treat is about to become your new favorite dessert.

Any great chef will tell you that presentation is as important as taste. And although other banana puddings taste delicious, they may not look as impressive as a Chessboard dessert.

This layered banana pudding with Chessmen recipe is a dessert that looks as good as it tastes. It has a layer of Chessmen cookies, followed by fresh banana slices, rich cheesecake pudding, and more cookies on top.

The magic of this dessert lies in its texture, which is slightly thicker than a typical pudding. This allows it to be cut neatly into individual ‘Chess piece’ squares.

And did I mention the sweet and creamy banana flavor? Are you ready to say goodbye to the shapeless yellow pudding blob? Then say hello to a better way to serve this classic dessert.

Why You Will Love This Recipe

  • Perfect for Parties. The crowd-pleasing appearance, deliciously addictive taste, and convenient individual servings make this recipe a great choice to serve at your next potluck. Chessmen cookies are always a big hit.
  • Easy and Affordable. You need just a few inexpensive and readily available ingredients. This is a great go-to recipe that can be easily made without breaking the bank.
  • Great for Summer. The best banana pudding recipe is served chilled and full of fresh fruit. That makes it an excellent alternative to ice cream. You need a refreshing dessert to cool you off on a warm day.

Tips & Tricks

  • Because this pudding isn’t as thick as a cheesecake, it can be challenging to scoop out – especially the first piece.

    To help ensure that your servings hold their shape and look like Chess pieces, wait until the pudding is chilled and set. Then place it in the freezer for 30-60 minutes before slicing.
  • When slicing each square, try to make sure you’re cutting between the cookies on the bottom layer. This will guarantee that each piece has support on the bottom.
  • Feel free to throw in some other fresh fruit along with the banana layer. You can add sliced strawberries to make a strawberry banana pudding. Raspberries or blueberries would be great also.

Ingredients

ingredients for cream cheese Chessmen banana pudding
  • Fresh Bananas. Use 4 to 6 medium bananas, depending on how condensed you want your banana layers. I usually use more bananas in this recipe than in other banana puddings because there is only 1 layer of bananas.
  • Pepperidge Farm Chessmen Cookies. Chessmen cookies are rectangular butter cookies with a Chess piece icon imprinted on them. My son, the Chess player, loves these cookies.

    You can use different cookies if you want. But these cookies are the perfect size for the banana pudding squares.

    The spring version of Chessmen cookies comes with flower imprints instead of Chess images. Unless you are specifically looking for Chess icon cookies, other imprints are not a problem.

    Grab 2 packages of cookies. You may not need all the cookies in both packs, but you will be glad you have two bags.

    Often, you will find a few broken cookies. Layer those cookies on the bottom of the pan. Keep the perfect cookies on top.

    If you want to lean into the Chess theme, open each bag of cookies and sort them by Chess piece.
  • Cream Cheese. Cream cheese makes this recipe, unlike other banana pudding recipes you have tried. It makes it closer to a no-bake cheesecake recipe.

    If you are looking for a healthier alternative to cream cheese, you have a few choices that will work in this recipe. Neufchatel cheese is the best substitute.
  • Sweetened Condensed Milk. The sweet milk will sweeten and add moisture to the pudding.
  • Instant French Vanilla Pudding. No need to mix up the pudding. The dry mix sweetens and adds vanilla flavor.
  • Cool Whip. Thaw before using the Cool Whip. If you want, you can make your own whipped cream. It only takes 5 minutes, and I prefer it to Cool Whip.

Equipment

  • Handheld electric mixer. Because of the cream cheese, this recipe may be difficult to mix by hand.
  • Optional: Make your own Chessboard with a cake board and parchment paper squares. It will be a huge hit with Chess fans.

How to Make Banana Pudding with Chessmen Cookies Recipe

Step 1: Soften the cream cheese.

Cream cheese and evaporated milk in a bowl

Step 2: Combine cream cheese, sweetened condensed milk, and instant pudding mix in a large bowl. Mix with an electric hand mixer.

Mixing vanilla pudding mix into cream cheese for banana pudding

Step 3: Fold in the whipped topping or homemade whipped cream.

mixing Cool Whip into cream cheese banana pudding

Optional: Make whipped cream by whipping heavy cream and sugar in a medium mixing bowl. Use the whip attachment on your hand mixer.

Step 4: Slice the bananas. Sprinkle the sliced bananas with lemon juice (or Fruit-Fresh, a fruit preserving powder often found in the canning section of the grocery store). This is optional but will help prevent the bananas from browning.

Step 5: Layer the Chessmen cookies in a single layer on the bottom of a 9 X 13 glass pan or another square or rectangular pan.

layer of Chessmen cookies in a pan

Step 6: Layer the banana slices on top of the cookies. I like to make a dense layer of slices close together since there will only be one layer of bananas.

banana layered on top of Chessmen cookies in the pan

Step 7: Spread the pudding mixture on top of the bananas. Use the whole cream cheese combination. This is the primary part of the banana pudding recipe.

cream cheese banana pudding layer in pan

Step 8: Finish by layering the remaining cookies on the pudding. Make sure the cookies face the direction you want and that the imprint is face-up.

cream cheese banana pudding with chessmen cookies

I like to set the cookies up as if in a Chess game. This works best if you have a square pan.

Two rows of cookies are right side up. The other two rows look upside down from my angle. Just as it would look in a real Chess game.

Step 9: Cover the banana pudding with plastic wrap. Refrigerate for at least 2 hours, but 4 is even better. You want the cream cheese to firm up for easy cutting.

Step 10: Before cutting, place the pan in the freezer for 30 minutes, so the pudding is very firm. Serve by cutting the cheesecake along the lines of the cookie. The first piece will be the hardest to get out.

The first time you try to scoop it out, you may get frustrated. Try removing the cookie temporarily before scooping the first piece. Then replace the cookie before serving.

How Early Can You Make Banana Pudding with Chessmen Cookies?

This banana pudding recipe is very easy to make early. Make it 24 to 48 hours ahead.

  • Wait to put the cookies on. If you make it more than one day early, don’t put the Chessmen cookies on top until you are ready to serve it. Then you know your cookies will still have a crunch. No soggy cookies here.
  • Take steps to avoid brown bananas. The minute bananas are exposed to oxygen, browning starts. Sprinkle with lemon juice or Fruit-Fresh to minimize the browning. Especially if you plan to make the pudding early.

How to Store Leftover Pudding

Chessmen banana pudding leftovers

Store leftover banana pudding in an airtight container for best results.

However, scooping the pudding into another container may not be easy. You may find it easier to tightly cover the serving dish with plastic wrap or aluminum foil.

How Long Does Chessmen Banana Pudding Last? Cream cheese banana pudding lasts up to 4 days in the refrigerator. Keep the pudding covered adequately, so it doesn’t take on any fridge odors.

The only problem you may see is browning bananas and softening cookies on top if it is stored for longer than a day.

Can You Freeze Chessmen Banana Pudding?

Thanks to the cream cheese, this pudding freezes well. The only minor issue may be browning bananas when frozen. The fruit may not look quite as pretty after you freeze it, but it will still taste great!

You can also look for tips on keeping the bananas fresh in my post on preparing banana pudding the day before.

FAQ

How is this different from classic banana pudding?

There are several key differences from a traditional banana pudding recipe. Unlike classic banana pudding, this recipe uses cream cheese.

It will not quite be the creamy banana pudding from the original recipe you are used to. The cream cheese gives it a slightly different (but still delicious!) flavor. And it allows it to hold its shape better.

The layers do not repeat. Each piece is filled with a thick cheesecake layer sandwiched between the cookies.

Chilling is required for this recipe since it needs to set.

And finally, it uses a different cookie variety than the original. Chessmen cookies are butter cookies with a richer flavor than the Nilla wafers used in the classic version.

Can I substitute a different cookie for the Chessmen?

Sure – if you don’t have Chessmen butter cookies, you can use traditional vanilla wafers instead.

Try shortbread cookies, graham crackers, or any other sturdy cookie with a mild flavor.
There are a variety of cookies that work great in any banana pudding.

What kind of pan should I use?

This is usually made in a 9 x 13 Pyrex glass pan, but it would also work in a 12 x 12 square cake pan or just about any square or rectangular serving dish.

How to Make a Chessboard for Serving

Chessmen banana pudding squares on a Chess board

It is a breeze to make a mock Chessboard. Use a large square cake board. A 12 X 12-inch or 16 X 16-inch cake board works best.

You will also need 3 X 3-inch natural color parchment paper squares.

Line the parchment paper squares on the cake board, skipping every other space. Then you will have a brown (parchment paper) square and a white (cake board color) square.

Place each pudding “Chess piece” on a small plate and then place it on your Chessboard.


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Yield: 20 servings

Cream Cheese Banana Pudding with Chessmen Cookies

squares of Chessmen banana pudding with cream cheese

Make the best cream cheese banana pudding with Chessmen cookies recipe (cream cheese, pudding, bananas, cookies). Firm no-bake dessert holds its shape.

Prep Time 15 minutes
Chill Time 2 hours
Total Time 2 hours 15 minutes

Ingredients

  • 1 (8 oz.) package of cream cheese, softened
  • 1 (14 oz.) can of sweetened condensed milk
  • 1 (3.4 oz.) package of instant vanilla pudding
  • 1 (8 oz.) tub of Cool Whip, thawed OR 2 cups of whipped cream
  • 4 to 6 medium-sized bananas
  • 2 packages of Pepperidge Farm Chessmen cookies

Instructions

  1. BRING the cream cheese to room temperature.
  2. COMBINE the softened cream cheese, sweetened condensed milk, and instant pudding mix in a large bowl. Mix with an electric hand mixer.
  3. FOLD in the whipped topping or homemade whipped cream.
  4. SLICE the bananas. Sprinkle the sliced bananas with lemon juice (or Fruit-Fresh, a fruit preserving powder often found in the canning section of the grocery store). This is optional but will help prevent the bananas from browning.
  5. LAYER the Chessmen cookies in a single layer on the bottom of a 9 X 13 glass pan or another square or rectangular pan.
  6. STACK the banana slices on top of the cookies. I like to make a dense layer of slices close together since there will only be one layer of bananas.
  7. SPREAD the pudding mixture on top of the bananas. Use the whole cream cheese combination. This is the primary part of the banana pudding recipe.
  8. FINISH by layering the remaining cookies on the pudding. Make sure the cookies face the direction you want and that the imprint is face-up.
  9. COVER the banana pudding with plastic wrap. Refrigerate for at least 2 hours, but 4 is even better. You want the cream cheese to firm up for easy cutting.
  10. FREEZE for 30 minutes before cutting, so the pudding is very firm.
  11. CUT the cheesecake along the lines of the cookie. The first piece will be the hardest to get out.
  12. REFRIGERATE leftovers for up to 4 days.

Notes

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Nutrition Information

Yield

20

Serving Size

1 square

Amount Per Serving Calories 74Total Fat 3gSaturated Fat 2gTrans Fat 0gUnsaturated Fat 1gCholesterol 7mgSodium 20mgCarbohydrates 12gFiber 1gSugar 7gProtein 1g

Nutrition information is an estimate only and may vary based on individual ingredients added and cooking methods used.


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