Homemade Banana Pudding Cups
From-scratch vanilla pudding, fresh bananas, and buttery Chessmen cookies, layered in individual cups. Make-ahead and perfect for a crowd.
Equipment
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 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
Make ahead: Assemble the cups 8 to 24 hours before serving and keep them covered in the fridge. That chill is what softens the cookies into cake-like layers, so it is not a step to skip. You can also make the pudding up to 2 days ahead; press plastic wrap directly on the surface so it does not form a skin.
Whipped cream: Best made fresh and piped on right before serving. In a pinch, you can make it up to 24 hours ahead, cover it well, and keep it in the fridge.
Storage: Covered in the fridge, these keep 3 to 4 days. The cookies soften a little more each day, so they are at their best in the first day or two.
Cookies: Pepperidge Farm Chessmen give the buttery, shortbread bite. Nilla wafers are the classic swap if that is what you have.
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