Preheat the oven to 350 degrees F. Spray an 8-inch round pan with nonstick spray (or rub with a little bit of butter). Sprinkle the bottom of the pan with 2 tablespoons of brown sugar.
In a small bowl, whisk together 3/4 cup brown sugar with the melted butter. Arrange pineapple slices into the bottom of your prepared pan (5 around the edges and 1 in the middle... snuggle them in there). Place a cherry in the middle of each pineapple slice. Spoon the butter/sugar mixture over the pineapple slices. In a small bowl, whisk together 1/4 cup sour cream, eggs, pineapple juice and vanilla. Set aside.
In a large bowl, whisk together the flour, sugar, baking powder, salt and baking soda. Add the remaining 1/4 cup sour cream and the softened butter to the bowl, and use an electric mixer to incorporate it into the dry ingredients until smooth. Bump up the speed to medium and beat until fluffy. Add the egg mixture and beat again until the batter is smooth- about 2 minutes.
Spread the batter evenly over the pineapple slices. Bake 40 minutes (or until golden). Cool for 5 minutes, then place a serving plate on top of the pan and carefully turn over and coax the cake out of the pan and onto the serving plate. If any of the pineapple sticks to the pan, just pull it out of the pan and put it in its place on the cake. Drizzle any remaining pan juices over the cake. Let cool, then slice and serve.