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Chessmen Banana Pudding

close up shot of a slice of chessmen banana pudding on a spatula
Creamy, decadent, and irresistible, this homemade classic chessmen banana pudding is a delicious, rich dessert you'll love!
Prep Time 30 mins
Chill Time 4 hrs
Total Time 4 hrs 30 mins
Course Dessert
Cuisine American
Servings 12
Calories 733 kcal


  • 14 ounces sweetened condensed milk
  • 12 ounces frozen whipped topping thawed
  • 2 bags Pepperidge Farm Chessmen cookies
  • 6 to 8 bananas sliced
  • 2 cups milk
  • 5 ounces instant French vanilla Pudding
  • 8 ounces cream cheese softened


  • Using a 9 x 13 pan layer the bottom of the pan with one bag of cookies (use any broken ones for the bottom).
  • Layer the sliced bananas over the top of the cookies.
  • In a large bowl combine the milk and pudding mix using an electric mixer, about 5 minutes until it starts to get thick.
  • In another large bowl combine the cream cheese and sweetened condensed milk with the mixer until smooth.
  • Fold the whipped topping into the cream cheese mixture.
  • Add the cream cheese mixture to the pudding mixture and stir until well blended or you could use the mixer you were already using!
  • Pour the mixture over the cookies and bananas.
  • Place the remaining cookies on top of this mixture.
  • Carefully cover with plastic wrap. Refrigerate at least 4 hours until ready to serve. Can be made the day before and refrigerated overnight.


TIP: If there are any broken cookies in your bag, use them on the bottom. Save all of the prettiest cookies for the top of your pudding.
TIP: Make sure your cream cheese is at room temperature, otherwise, you may end up with lumps in your mixture.
TIP: Make sure you don't skip the chilling step. It's important to give your dessert time to let all the flavors mingle and soften the cookies slightly.


Sodium: 609mgCalcium: 208mgVitamin C: 6mgVitamin A: 531IUSugar: 55gFiber: 3gPotassium: 520mgCholesterol: 52mgCalories: 733kcalSaturated Fat: 14gFat: 33gProtein: 11gCarbohydrates: 100gIron: 2mg