Preheat oven to 350° F. Mix brown sugar and 1/3 cup butter in a bowl. Stir in 1
teaspoon vanilla and cinnamon. Spread evenly over the bottom of an ungreased 9" cast
iron skillet or a 9" x 9" baking pan. Heat until the brown sugar melts.
Arrange pineapple slices over the brown sugar mixture. Place a cherry half in the middle
of each slice. Beat egg yolks in a mixer bowl until thickened. Gradually add 1/2 cup sugar,
beating constantly until blended.
Mix flour, baking powder and salt together in a large mixing bowl. Add shortening, 1/4
cup butter, pineapple juice, half and half, buttermilk and 1 teaspoon vanilla. Beat until
blended, scraping the bowl occasionally. Mix in egg yolk mixture. Fold in stiffly beaten
egg whites.
Spoon the batter into the prepared skillet. Bake for 35 - 40 minutes or until a cake
tester comes out clean. Invert the skillet onto a serving platter, allowing the skillet to
rest on the cake for several minutes before removing.