Preheat oven to 300° F. Line a baking sheet with parchment paper. Remove banana peel and place banana on baking sheet. Gently mash up the banana with a fork. Roast for 30 minutes. Set aside to cool.
Add butter to large saucepan over medium heat. Butter will begin to foam and then brown quickly. Stir constantly during entire process. Add brown butter to a medium bowl and set aside to cool for 10 minutes.
Add dark brown sugar and granulated sugar to bowl with brown butter. Mix until combined.
Add the egg, vanilla extract, and banana. Mix until combined.
Add salt, baking soda, and all-purpose flour and mix until just combined.
Stir in chocolate chips. Be careful not to over mix.
Scoop out 12 cookies using a #20 (3 tablespoon) cookie scoop.
Top each cookie with a few more chocolate chips. Press them gently into the dough.
Roll each cookie in the cinnamon sugar.
Line a baking sheet with parchment paper and preheat oven to 350° F. Place each cookie about 2 inches apart on the prepared baking sheet. Bake for 13-14 minutes or until the edges are set and the cookies have puffed up. Allow to cool before eating.