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Chessman Banana Pudding

Slice of Chessman banana pudding on a blue plate, showing layers of creamy pudding, bananas, and soft cookies topped with whipped cream and a toasted design.

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A no-bake Southern classic dessert made with layers of creamy French vanilla pudding, fresh bananas, whipped topping, and buttery Chessmen cookies. This easy banana pudding is perfect for holidays, parties, and any time you need a crowd-pleaser.

Ingredients

Scale
  • 1 (3.4-ounce) box of French vanilla instant pudding mix
  • 2 cups whole milk, cold
  • 1 (14-ounce) can of sweetened condensed milk
  • 1 (8-ounce) tub of Cool Whip, thawed
  • 34 ripe bananas, sliced (optional: toss in 1 tsp lemon juice)
  • 2 (7.25-ounce) packs of Pepperidge Farm Chessmen Butter Cookies
  • 1 (11-ounce) box of Nilla Wafers, crushed (optional)

Instructions

  1. In a large mixing bowl, whisk together pudding mix and cold milk until smooth, about 2–5 minutes.
  2. Add sweetened condensed milk and mix until fully combined.
  3. Gently fold in Cool Whip until light and fluffy.
  4. Chill pudding mixture in the refrigerator for 5–10 minutes to thicken.
  5. In a serving dish, layer sliced bananas on the bottom.
  6. Spread a layer of pudding mixture over bananas.
  7. Sprinkle a layer of crushed Nilla wafers (if using).
  8. Add a single layer of Chessmen cookies.
  9. Repeat the layers until all ingredients are used, finishing with Chessmen cookies on top.
  10. Chill in the refrigerator for at least 4 hours or overnight before serving.

Notes

  • Toss bananas in lemon juice to prevent browning.
  • Use cold milk and properly thawed Cool Whip for best texture.
  • Let dessert chill overnight for a creamier result.
  • Add caramel drizzle or fresh whipped cream on top before serving.
  • Layer in small cups or jars for individual servings.

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