Preheat oven to 350°F (175°C).
In a small bowl, mash the softened butter, 1/3 cup brown sugar, and ground cinnamon together until it forms a thick paste.
Take half of the cinnamon butter paste and generously smear it all over the bottom and sides of a 10-inch cast iron skillet. Set aside.
In a large bowl, thoroughly mash the overripe bananas. Whisk in the melted butter.
Add the granulated sugar, brown sugar, eggs, and vanilla extract to the bananas. Whisk until completely smooth.
Sprinkle the flour, baking soda, and salt over the wet ingredients. Gently fold with a spatula until just combined. Do not overmix.
Pour the batter into the coated cast iron skillet and smooth the top.
Drop small dollops of the remaining cinnamon butter evenly across the top of the batter. Use a butter knife to gently swirl it into the surface.
Bake at 350°F for 30 to 35 minutes, or until the edges are golden and a toothpick inserted into the center comes out with just a few moist crumbs.
Remove from oven and let cool in the skillet for 15-20 minutes before slicing into wedges. Serve warm!