Banana Pudding Chessman Dessert: Revisited

This recipe came up in one my searches recently and I was unable to stop thinking about it. When we were out shopping I picked up the ingredients to make it. I think we all think it was better than we remembered it. I made a small change to the recipe because I couldn’t find a 5 oz box of pudding mix and made it a bit thicker.

I love Pepperidge Farms Chessman Cookies. They are rich and buttery. They usually have all the chess pieces embossed on the front but these were a special that had spring scenes on them. If you don’t have chessman any real buttery cookie will do.

Banana Pudding Chessman Dessert

  • Servings: 12
  • Difficulty: easy
  • Print


  • 1 (12 oz) container frozen whipped topping, thawed
  • 1 (14 oz) can sweetened condensed milk
  • 1 (8 oz) package cream cheese, softened
  • 2 1/2 cups whole milk or fat-free half and half
  • 2 (3.4 oz) box French Vanilla Instant Pudding
  • 8-10 bananas, thinly sliced
  • 2 bags Chessman cookies


  1. Cover the bottom of a 13″ x 9″ casserole dish with Chessman cookies.
  2. Cover the cookies by layering the banana slices on top.
  3. In a bowl beat the milk and pudding mix until smooth.  In a second bowl beat the cream cheese and sweetened condensed milk until smooth. Fold the whipped cream into the cream cheese mixture. Fold the two bowls together.
  4. Pour the mixture over the bananas and smooth out.
  5. Cover the top with the remaining Chessman cookies.

9 Comments Add yours

  1. trkingmomoe says:

    this is my son’s favorite pudding. I make the Paula Dean’s recipe. Yours looks wonderful. Thanks for sharing this recipe.

    Liked by 1 person

    1. koolaidmoms says:

      Thank you! I love Paula Dean too.

      Liked by 1 person

  2. Those little cookies are so much fun!

    Liked by 1 person

    1. koolaidmoms says:

      They are so good and cute too!

      Liked by 1 person

  3. elamorkitchencom says:

    You are so creative..this is great idea..thanks for sharing this idea..Have a blessed weekend

    Liked by 1 person

    1. koolaidmoms says:

      Thank you! You too!


  4. This sounds delicious, Marci

    Liked by 1 person

    1. koolaidmoms says:

      Thank you!


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