Step 1

Preheat oven to 350 degrees F.  Place ¼ cup butter in a 9-inch round pan.  Put pan in the oven until the butter melts.  Sprinkle the brown sugar in an even layer over the melted butter.

Step 2

Place one whole pineapple ring in the center of the pan.  Cut the other pineapple slices in half, and arrange them in a fanned manner.  You will use about 6 whole slices, or 12 halves, to cover the bottom of the pan.  Place a cherry in the center of each pineapple slice.

Step 3

In a mixing bowl, beat butter for 2 minutes.  Add sugar and vanilla and continue beating with electric mixer until blended.  Add eggs, beating well.  Combine flour, baking powder and salt in a small bowl.  Add to the butter mixture, alternating with the whole milk.  Beat for 3 minutes after all is added.

Step 4

Pour cake batter into cake pan and spread evenly over the pineapple.  Bake for 50 minutes or until a toothpick comes out clean and top is browned.

Step 5

Immediately after removing from oven, place a cake plate or platter on top of the cake pan.  Flip the plate and pan upside down.  Leave pan over cake for a couple of minutes allowing the brown sugar mixture to drizzle over cake.  Remove pan.  Serve warm.

Step 6

Loosely cover and store cake in the refrigerator for best results.