2/3 C packed light brown sugar
1/3 + 1/4 C butter, softened, divided
2 tsp. vanilla extract, divided
1/2 tsp. cinnamon
9 canned pineapple slices
9 maraschino cherry halves
2 egg yolks
2 egg whites, stiffly beaten
1/2 C sugar
1 1/2 C flour
2 tsp. baking powder
3/4 tsp. salt
1/4 C shortening
1/4 C pineapple juice
1/4 C half and half
1/4 C buttermilk
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.