⅔ cup packed light brown sugar
⅓ cup unsalted butter, softened
1 teaspoon vanilla extract
½ teaspoon cinnamon
9 canned pineapple slices
2 egg yolks
½ cup sugar
1½ cups flour
2 teaspoons baking powder
¾ teaspoon salt
¼ cup shortening
¼ cup unsalted butter, softened
¼ cup pineapple juice
¼ cup half and half
¼ cup buttermilk
1 teaspoon vanilla extract
2 egg whites, stiffly beaten

Preheat the oven to 350°.

Mix brown sugar and ⅓ cup butter in a bowl. 

1. Stir in 1 teaspoon vanilla and cinnamon. 

2. Spread evenly over the bottom of an ungreased 9-inch cast-iron skillet or 9x9-inch baking pan.

3. Heat until the brown sugar melts.

4. Arrange the pineapple slices over the brown sugar mixture. 

5. Place a cherry half in the middle of each slice.

6. Beat egg yokes in a mixer bowl until thickened. 

7. Add ½ cup sugar gradually, beating constantly until blended.

8. Mix flour, baking powder and salt in a mixer bowl. 

9. Add shortening, ¼ cup butter, pineapple juice, half-and-half, buttermilk and 1 teaspoon vanilla. 

10. Beat until blended, scraping the bowl occasionally.

11. Mix in egg yolk mixture.

12. Fold in whipped egg whites. 

13. Spoon the batter into the prepared skillet.

14. Bake for 35 to 40 minutes or until a wooden pick inserted in the center comes out clean.

15. Invert the skillet onto a serving platter, allowing the skillet to rest on the cake for several minutes before removing.