Preheat your oven to 350°F.
In a mixing bowl, combine all your ingredients except for the chocolate chips and nuts. Mix until combined. Add chocolate chips and nuts if desired, and stir to combine.
Pour your brownie batter into a greased pan and bake for 20-30 minutes. If you like your brownies to be on the gooey side, it will take about 20-25 minutes, cook longer if you prefer.
In a saucepan, heat ½ cup of heavy cream over medium heat until it is warm. Do not allow it to boil. While your cream is heating, in a mixing bowl, add egg yolks and granulated sugar. Whisk until your eggs become a light yellow and your mixture is fluffy. Remove your cream from the heat and pour it into your mixing bowl. Whisk together on low, until combined. Pour your entire mixture back into the saucepan.
Place saucepan over medium heat and whisk until your mixture thickens. Your mixture must also reach 160°F. Once your mixture thickens, remove it from the burner. Add in sea salt, vanilla extract, instant vanilla pudding mix, cinnamon, and ripe bananas. Whisk to combine. In a separate mixing bowl, pour in your 1 ½ cup remaining heavy cream. Whisk on high until stiff peaks form. Add powdered sugar and whisk to combine. Add your banana mixture to your whipped cream and whisk on low, to combine.
Once your brownie has been cooked and mostly cooled, and your banana pudding is prepared, it is time to assemble your dessert. Start by adding a layer of banana pudding on top of your brownie. Next place scoops of cool whip throughout the top of the brownie. Top with vanilla wafers and cookie crumbs if desired.
Place your banana pudding brownies in the fridge and allow for them to cool if desired.
Once chilled, slice the brownies into pieces and serve. This dessert can be enjoyed warm or cold. Enjoy!