Preheat your oven to 350°F (175°C) and line a cupcake pan with cupcake liners.
Cream together 1/4 cup of softened butter and 3/4 cup of granulated sugar until light and fluffy. Add in 1 large egg and 1 teaspoon of vanilla extract, mixing until well combined.
In another bowl, whisk together 2/3 cup of all-purpose flour, 1 1/2 heaping tablespoons of cocoa powder, and a pinch of salt. Gradually mix the dry ingredients into the wet mixture until just combined. Fold in 1/3 cup of mini chocolate chips that have been lightly tossed in flour.
In a separate bowl, combine 1 1/3 cups of flour, 1 1/4 teaspoons of baking soda, 1/4 teaspoon of salt, 1/2 teaspoon of cinnamon, and a pinch of nutmeg. In another bowl, mash 3 large ripe bananas and mix them with 3/4 cup of brown sugar, 1 teaspoon of vanilla extract, 1 egg, 1/4 cup of sour cream, and 1/2 cup of melted butter.
Gently fold the banana mixture into the dry ingredients until just combined. Then, add the brownie batter and swirl it through the banana bread batter for a marbled effect.
Scoop the batter into the prepared cupcake liners, filling each about 2/3 full. Bake for 20-22 minutes, or until a toothpick inserted into the center comes out clean. Allow the cupcakes to cool completely in the pan before transferring to a wire rack.
In a large mixing bowl, beat together 3/4 cup of softened butter and 8 ounces of cream cheese until smooth. Gradually add in 1 3/4 cups of loosely packed brown sugar and 1 1/2 cups of powdered sugar, mixing until fluffy. Stir in 1 tablespoon of vanilla extract.
Once the cupcakes are completely cool, generously frost each with the brown sugar frosting.