Make the Vanilla Pudding:
- Add the milk, cream, sugar, and salt to a large pot. Heat over medium, whisking often, and bring to a simmer.
- While the milk mixture is heating to a simmer, combine the egg yolks and cornstarch in a medium bowl. Whisk vigorously until the mixture lightens in color.
- Slowly stream the milk mixture into the egg yolks while whisking the egg yolks constantly to prevent them from scrambling. Add about 1/2-1 cup of the milk mixture in total to the egg yolks. Whisk to combine, then pour the egg yolk and milk mixture back into the pot.
- Whisk the pudding constantly. Once it starts to bubble, set a 30 second timer and continue to whisk as it cooks.
- Take the pudding off the heat and whisk in the butter and vanilla, then pour it through a sieve and into a large bowl or container.
- Press plastic wrap against the surface of the pudding. Allow to cool to room temperature, then refrigerate while you make the cupcakes.
Make the Banana Cupcakes:
- Preheat oven to 350°F (177°C). Line a muffin pan with 12 paper liners. If you have a second muffin pan, line it with another 2 liners because this recipe makes 14 cupcakes. If you only have one muffin pan, you can just bake the first 12 cupcakes, rinse off the pan, and then bake the last 2 after.
- In a medium bowl, whisk the cake flour, baking powder, cinnamon, baking soda, and salt. Set aside.
- In a large bowl, whisk the mashed banana, brown sugar, and white sugar. Once combined, whisk in the buttermilk, oil, egg, and vanilla.
- Add the dry ingredients to the wet ingredients and whisk until combined.
- Divide the batter between the 14 liners, filling 2/3-3/4 of the way to the top. A large cookie scoop makes this easy.
- Bake for 16-20 minutes, or until a toothpick comes out clean or with a few moist (but not wet) crumbs.
- Set the pan over a wire rack and allow the cupcakes to cool for 10 minutes before removing them from the pan and allowing them to cool completely.
Make the Whipped Cream & Decorate:
- Add the cream cheese, powdered sugar, and vanilla to the bowl of a stand mixer. Whip using a whisk attachment on high speed for 5 minutes.
- Reduce speed to medium-low and slowly pour in the heavy cream. Once all of the cream has been added, increase the speed to high and whip until the mixture forms stiff peaks. Stop and scrape down the sides and bottom of the bowl periodically to make sure all of the cream cheese combines with the heavy cream.
- Remove the centers of each cupcake using a large round piping tip, a knife, or a cupcake corer. Fill with the chilled pudding. I like to pipe the pudding inside, but using a spoon or squeeze bottle instead also work.
- Decorate the filled cupcakes as desired using the whipped cream. You can either spread it on with a knife or fill it into a large piping bag and pipe it on. I used 18-inch piping bags and a Wilton 1M piping tip to decorate the pictured cupcakes.
- Top each cupcake with a Nilla wafer, additional crushed Nilla wafers, and a drizzle of salted caramel if desired.
- Store leftover cupcakes in an airtight container in the refrigerator for up to 2-3 days. Bring to room temperature before serving.