Prep Your Ingredients: Use blender or food processor to puree one banana until smooth. Alternatively, you can mash it by hand with a kitchen spoon, fork, or mortar and pestle. Cut cream cheese into roughly one-inch cubes. Dissolve cornstarch in ⅓ cup milk in a small bowl. Set aside.
3 bananas, 8 ounces cream cheese, 3 cups evaporated milk, ⅓ cup cornstarch
Make the Custard: Whisk together granulated sugar, brown sugar, and sea salt in small saucepan. Mix in the egg yolks, followed by remaining milk, then place saucepan on stove top over medium-low flame.
½ cup granulated sugar, ¼ cup brown sugar, ¾ teaspoon fine sea salt, 6 egg yolks
Whisk mixture regularly (every 10-20 seconds or so) and cook until heated through (about 10 minutes, do not bring to a boil) then stir in the cream cheese, followed by the banana puree, and the cornstarch slurry, fully incorporating each ingredient before adding the next.
Keep stirring until mixture is thickened then remove from heat and stir in butter, vanilla extract, and bourbon. If your pudding is lumpy at this stage, see recipe notes for remedy.
2 tablespoons unsalted butter, 1 tablespoon vanilla extract, 1 teaspoon bourbon whiskey
Transfer the custard to a medium mixing bowl then fill a large mixing bowl halfway with ice water and carefully place the bowl of custard into the ice bath to cool.
Make the Whipped Cream: While the custard cools, add heavy cream and powdered sugar to bowl of stand mixer with whisk attachment fitted or mixing bowl with hand mixer and beat on medium speed until mixture is uniform, thickened, and fluffy (about 15 minutes).
3 cups heavy cream, 1 tablespoon powdered sugar
Assemble the Pudding: Add Nilla wafers to oblong baking dish and use kitchen spoon to crush them into pieces in the bottom of dish. Slice remaining bananas and layer them on top of the cookie crumbs.
48 Nilla Wafers
Gently fold the cooled custard into the whipped cream until uniform then spoon and spread pudding into oblong dish in an even layer. Be gentle when adding the pudding (don’t plop it in) and avoid dumping it all in one spot so that the cookie crumbs and banana pieces don’t move around too much. Smooth out the pudding as much as possible then top with chessman cookies, cover with plastic wrap, and refrigerate until set (at least five hours). Serve with fresh grated nutmeg, if desired.
22 chessman cookies, fresh grated nutmeg