In the large bowl of a stand mixer,or in a large mixing bowl with an electric mixer, or by hand, cream 1 cup of room temperature butter and sugar together.
Add in the sour cream, eggs, and vanilla and fully combine at medium speed.
In another separate bowl combine the dry ingredients, the flour, baking soda, and salt.
Add the dry ingredients to the wet ingredients in the stand mixer and combine at a low speed to create the cake batter. Set aside. In a small pot, melt 4 tablespoon of butter with 2 tablespoon brown sugar over medium heat.
Spray 2 regular muffin tins with non stick spray to make 24 mini cakes. Add about ½ teaspoon of the melted butter and brown sugar mix to the bottom of each muffin tin.
Cut 12 canned pineapple rings in half, and then make several slits ¾ of the way through each pineapple piece, on the outside. Cut 12 maraschino cherries in half. In each cupcake spot, on top of the butter and brown sugar mixture add ½ of the pineapple ring, using your fingers to make it form a circle. Add ½ a maraschino cherry to the centre of each one in the bottom of each cup. Add the batter on top of the pineapple slices, evenly divided between the 24.
Bake the mini pineapple upside down cakes at 325 degrees for about 20 minutes, until a toothpick inserted in the middle comes out clean, and the middle springs back when you push it down with your finger.
Turn the mini pineapple upside down cakes out onto a cooling rack to cool. When cool, remove from the wire rack and store in an airtight container. Serve them with whipped cream.