Preheat oven to 350 degrees. Grease a bundt pan and coat with a thin layer of flour. Set aside.

To make the caramel sauce, in a medium saucepan, bring 1 cup brown sugar sugar, heavy cream, 4 Tbsp unsalted butter, and pinch of salt to a boil over medium heat. While stirring continuously, cook until the mixture thickens and deepens in color, approximately 7-9 minutes. Add 1 Tbsp vanilla extract and bourbon and continue to cook for another 1-2 minutes. Remove from heat and allow to cool for 15 minutes.

Line the bottom of the bundt pan with half of the sliced bananas. Drizzle half of the caramel sauce over the bananas.

Combine 1 cup brown sugar with cinnamon in a bowl. Cut 15 dinner rolls in half and roll each piece in the cinnamon sugar mixture. Layer the sugar coated rolls over the bananas and caramel in the pan.

Add the remaining banana slices in an even layer over the rolls. Drizzle the remaining caramel sauce over the bananas.

Cut the remaining rolls in half, rolling each piece in the cinnamon sugar, and layer on top of the bananas and caramel once again. Add the 3 Tbsp of melted butter to the cinnamon sugar mixture and, once combined, pour over the final layer of rolls. Pour 1 tsp of vanilla over the final layer of rolls as well.

Cover the pan with cling wrap and allow to rise in a warm place for 45 minutes to 1 hour.

Place the bundt pan on a rimmed baking sheet and bake for approximately 40-45 minutes. Turn out onto a large serving dish that is at least a couple inches wider than the bundt pan when turned out. Serve immediately.