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Place the butter, brown sugar, and cinnamon in a large skillet over medium heat. Constantly stir as the butter and sugar melt down. Add the bananas and cook until softened and slightly caramelized, about 3 minutes. *If you prefer a little more texture in your banana pudding, only cook the bananas for about 1-2 minutes.* Remove from heat and set aside.
Combine the milk, heavy cream, sugar, and salt in a medium saucepan over medium heat. Whisk until all the sugar has dissolved, then bring to a gentle simmer, whisking occasionally. Working quickly as the milk mixture begins to simmer, whisk the egg yolks and cornstarch together in a medium heatproof bowl until very thick and smooth. Very slowly stream in about 3/4 cup (180ml) of the simmering milk to slightly warm the egg yolk mixture. Then, in a very slow stream, whisk the egg yolk mixture into the pan. While continuously whisking, cook until the mixture is thick and big bubbles begin bursting at the surface, about 1 minute. Remove the pan from heat and whisk in the vanilla extract and butter. Makes about 4 cups of pudding.
Use an ungreased 9-inch or any 2.5 quart baking dish. Line half of the vanilla wafers on the bottom. Evenly top with half of the caramelized bananas. Give the pudding a quick stir. If it has thickened considerably and isn’t pourable, whisk in a splash of milk to help thin out. Pour half of the warm pudding on top. Use a spoon to evenly spread around. Evenly top with remaining vanilla wafers, then the remaining caramelized bananas. Pour the rest of the pudding on top and spread into an even layer. Set aside, covered or uncovered, at room temperature or in the refrigerator as you make the whipped cream.
Using a hand mixer or a stand mixer fitted with a whisk attachment, whip the heavy cream, confectioners’ sugar, vanilla extract, and cinnamon on medium-high speed until medium peaks form, about 3-4 minutes. Medium peaks are between soft/loose peaks and stiff peaks. Spread evenly on top of the pudding.
Cover the pudding tightly and refrigerate for at least 4 hours and up to 24 hours. The vanilla wafers will soften during this time. They may taste too soggy after 1 full day and the bananas will begin to release some liquid, so for best taste and texture, serve within 24 hours.
To serve, spoon into individual bowls. Cover and store leftovers in the refrigerator for up to 2 days. I don’t recommend freezing this because of the high volume of liquid in the pudding, whipped cream, and bananas. The caramelized bananas won’t thaw very nicely either.