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Southern Chessmen Cookie Banana Pudding Recipe

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4.1 from 49 reviews

This easy Southern-style banana pudding layers buttery Chessmen cookies, fresh bananas, and a rich, creamy vanilla filling made with instant pudding, cream cheese, and whipped topping. Assemble it ahead, then chill until set for a crowd-pleasing no-bake dessert.

Ingredients

For the layers

  • 2 packages Pepperidge Farm Chessmen Butter Cookies, divided
  • 3–4 large bananas, or more for a thicker layer

For the vanilla pudding filling

  • 1 package (5.1 ounces) vanilla instant pudding mix
  • 1 cup milk
  • 1 cup heavy cream

For the cream cheese mixture

  • 1 package (8 ounces) cream cheese, softened
  • 1 can (14 ounces) sweetened condensed milk
  • 1 container (8 ounces) whipped topping

Instructions

  1. Layer the cookies.

    Arrange a layer of Chessmen cookies across the bottom of a 13-by-9-inch baking dish, covering the base as evenly as possible. Reserve the remaining cookies for the top.

  2. Make the pudding.

    In a large bowl, whisk or beat the instant pudding mix with the milk and heavy cream for about 2 minutes, until the mixture begins to thicken. Set aside.

  3. Mix the cream cheese and condensed milk.

    In a separate bowl, beat the softened cream cheese and sweetened condensed milk until smooth and well combined.

  4. Fold in the whipped topping.

    Use a spatula to gently fold the whipped topping into the cream cheese mixture, keeping the mixture light and fluffy.

  5. Combine the fillings.

    Add the pudding mixture to the cream cheese mixture and stir or fold until the filling is evenly blended.

  6. Add the bananas.

    Slice the bananas and arrange them in an even layer over the cookies. Add a second layer if you prefer extra banana.

  7. Spread on the filling.

    Spoon the pudding mixture over the bananas and smooth it into an even layer, spreading it all the way to the edges of the dish.

  8. Finish with cookies and chill.

    Arrange the remaining Chessmen cookies over the top. Cover the dish tightly with plastic wrap and refrigerate for at least 4 hours, or overnight, until set and chilled.

Notes

  • Use softened cream cheese so it blends smoothly with the sweetened condensed milk.
  • For a more pronounced banana layer, add extra sliced bananas or arrange two layers.
  • Chilling overnight gives the pudding time to set and lets the cookies soften slightly.
  • Keep the dessert covered and refrigerated. For the freshest banana flavor and appearance, enjoy within 2–3 days.