In the bowl of a stand mixer or in a mixing bowl with an electric hand mixer, add the heavy cream and powdered sugar and beat on low speed, gradually increasing speed to high until stiff peaks form. Set aside.Skip this step if using Cool Whip. 1 ½ cups heavy cream, 1 ½ tablespoons powdered sugar
In a large mixing bowl, combine the milk and pudding mix. Blend well with a whisk. Set aside.
2 cups whole milk, 1 5-oz box instant vanilla pudding mix
In another mixing bowl, combine the cream cheese, smoothing it out with a spatula or wooden spoon. This helps prevent chunks of cheese cream from remaining in the mixture. Add the condensed milk. Use a hand mixer to mix until smooth.
1 8-oz package cream cheese, 1 14-oz can sweetened condensed milk
Fold the whipped cream into the cream cheese mixture using a spatula. Blend, being sure to scrape the bottom to ensure the mixture is fully and evenly combined.
Add the cream cheese mixture to the pudding mixture and fold together until well blended. Set aside.
Peel and slice bananas. TIP: To prevent the bananas from browning, place the slices in a bowl of cold water until ready to use. Blot them with paper towels before layering in the serving dish. 6-8 small to medium bananas
Arrange ⅓ of the Nilla wafers covering the bottom of the serving dish, overlapping if necessary. Next, layer ⅓ of the bananas, patting them dry before adding them, followed by ⅓ of the pudding mixture. Spread the pudding mixture almost to the edges to allow the layers to show through the sides of the glass serving dish. Repeat the layers twice more, garnishing with additional wafers or wafer crumbs on the top layer.
1 11-ounce box Nilla wafer cookies
Cover the dish tightly with plastic wrap and allow to chill in the fridge for at least 4 hours or up to 8 hours, but no longer. Use a long-handled spoon to reach the layers of the pudding and serve.