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A baking dish of banana pudding with cookies on top, partially served, sits on a marble surface next to a plate with a portion and a spoon.

Chessmen banana pudding

This chessmen banana pudding is thick and creamy with layers of fresh bananas, buttery cookies, and salted caramel in every bite. Rich, smooth, and perfectly sweet without being overpowering.
Prep Time 25 minutes
8 hours
Total Time 8 hours 25 minutes
Servings: 12 people
Course: Dessert
Cuisine: American

Ingredients
  

  • 5.1 oz box instant vanilla pudding mix
  • 5.1 oz box instant banana cream pudding mix
  • 3 cups cups cold milk
  • 8 oz cream cheese, softened
  • 7 oz can sweetened condensed milk
  • 1 tsp vanilla bean paste
  • 3 cups cold heavy cream
  • 1 Box Nilla Wafers
  • 1 package Pepperidge Farm Chessmen cookies
  • 4 fresh bananas, thinly sliced
  • 1/2 cup Salted caramel sauce, for drizzling

Equipment

  • hand mixer
  • measuring cups and spoons
  • 9x13 pan

Method
 

Make the Pudding

  1. In a large bowl, whisk together both instant pudding mixes and the cold milk for about one minute until the pudding begins to thicken. Place it in the refrigerator while preparing the whipped cream mixture.

Make the Cream Cheese Mixture

  1. In another large mixing bowl, combine the softened cream cheese, sweetened condensed milk, and vanilla bean paste. Using a hand mixer or handheld electric mixer, beat until completely smooth with no lumps remaining.
    Pour in the cold heavy cream and begin mixing on low speed. Gradually increase the speed until the mixture becomes thick and holds stiff peaks. Be careful not to overmix.

Fold Everything Together

  1. Remove the chilled pudding from the refrigerator and gently fold it into the whipped cream mixture until completely combined. The result should be a light, fluffy, creamy pudding mixture.
Assemble the banana pudding
  1. Spread a thin bottom layer of pudding into a 9×13-inch baking dish. Sprinkle a generous layer of crushed vanilla wafers over the pudding. Arrange nine Chessmen cookies on top.
    Drizzle with salted caramel sauce. Add half of the bananas in an even layer. Spread half of the remaining pudding mixture over the bananas.
    Repeat with another layer of crushed vanilla wafers, nine more Chessmen cookies, another drizzle of caramel, the remaining fresh banana slices, and the rest of the creamy pudding mixture.
    Finish the top layer with extra crushed vanilla wafers, the remaining Chessmen cookies, and one final drizzle of salted caramel. Cover tightly with plastic wrap and refrigerate overnight for the best results.

Notes

Storage

Store leftover banana pudding covered with plastic wrap or in an airtight container in the refrigerator for up to 3 days. Because of the fresh bananas, this dessert is best enjoyed within the first couple of days.
I don’t recommend freezing it, as the bananas and whipped cream can change texture once thawed.