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Homemade Banana Pudding Cups

Close up view of finished banana pudding cup.
These homemade banana pudding cups feature layers of luscious pudding, fresh bananas, and sweet cookies, all served in charming individual glasses or cups. It's a decadent dessert perfect for any occasion.
Sarah Allison
Prep Time 25 minutes
Cook Time 10 minutes
Total Time 12 hours 35 minutes
Serving Size 8

Ingredients

  • 2/3 cup (134 grams) granulated sugar
  • 1/4 cup (30 grams) cornstarch
  • 1/4 teaspoon (1g) Diamond Crystal kosher salt, for table salt, use about half as much by volume or the same weight
  • 2 1/2 cups whole milk
  • 4 large egg yolks
  • 2 tablespoons unsalted butter, cut into pieces
  • 1 1/2 teaspoons pure vanilla extract
  • 1 1/2 cup very cold heavy cream
  • 1 (8 ounce) package cream cheese, softened
  • 1 (14 oz) can sweetened condensed milk
  • 2 (7.25 oz) packages Pepperidge Farm Chessmen cookies
  • 4 large ripe bananas thinly sliced

Fresh Whipped Cream (for serving)

  • 2 cups cold heavy cream
  • 3 1/2 tablespoons granulated sugar or powdered sugar
  • 1 teaspoon vanilla extract

Instructions

Vanilla Pudding

  • Whisk together the sugar, cornstarch, and salt in a medium nonreactive saucepan.
  • Gently whisk in the milk until you have a smooth mixture. Then, whisk in the egg yolks until everything is smooth.
  • Cook over medium heat, whisking constantly until the first big bubbles pop and sputter.
  • Reduce the heat to low and cook, continuously whisking for 1 minute or more until thickened.
  • Remove from heat and transfer the pudding to a medium bowl. Stir in the butter and vanilla until combined.
  • Cover the top with plastic wrap pressed directly against the surface. Refrigerate for at least 1 hour and up to 4 hours.

Whipped Cream

  • Whip the heavy cream in the bowl of a stand mixer fitted with the whisk attachment until soft peaks form. Transfer to a separate bowl and set aside.

Cream Cheese mixture

  • In a stand mixer bowl fitted with a whisk attachment, beat the cream cheese and condensed milk until smooth. Add the vanilla pudding to the cream cheese mixture and whip until light and fluffy.
  • Transfer to a large bowl and fold in the whipped cream.

Assemble

  • Use clear individual serving cups, glasses, or jars to layer a chessman cookie, 3-4 banana slices, and pudding/whipped cream. Layer another chessman cookie, then 3-4 banana slices, and fill to close to the top with more of the pudding/whipped cream mixture.
  • Cover with plastic wrap and refrigerate for at least 8 hours and up to 24 hours before serving.
  • Right before serving, top with freshly whipped cream over the top.

Fresh Whipped Cream topping

  • Mix 2 cups of cold heavy cream, 3 tablespoons of sugar, and 1 teaspoon of vanilla extract in a bowl with a stand mixer. Use the whisk attachment and whip until you see soft peaks forming.
  • Before serving, top pudding cups with whipped cream (if desired).
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Notes

Prep Ahead Guide: This recipe is great for preparing ahead of time. Let it chill for at least 8 hours, but you can keep it in the fridge for up to 24 hours. You can also get the pudding ready beforehand if you like. If you're making the pudding ahead of time, place plastic wrap right on top of the warm pudding to prevent a "skin" from forming. You can store it in the refrigerator for up to 2 days. Making the whipped cream works best when done fresh. However, if necessary, you can make it ahead, cover it well, and let it chill in the fridge for up to 24 hours before using it.