1/4 cup butter or margarine
2/3 cup packed brown sugar
7 slices pineapple in juice (from 14-oz can), drained
1/3 cup crushed pineapple in juice, drained
7 maraschino cherries without stems
1 1/3 cups all-purpose flour
1 cup granulated sugar
1/3 cup shortening
1 1/2 teaspoons baking powder
1/2 teaspoon salt
3/4 cup whole milk
1 egg
1/2 teaspoon rum extract
Heat oven to 350°F. In a 8.5-inch or 9-inch round pan, melt butter in oven. Sprinkle brown sugar evenly over melted butter. Arrange pineapple slices over brown sugar. Place cherry in center of each pineapple slice. Sprinkle crushed pineapple to fill in all the gaps, including inside the center of the pineapple rings.
In medium bowl, beat remaining ingredients with electric mixer on low speed 30 seconds, scraping bowl constantly. Beat on high speed 3 minutes, scraping bowl occasionally. Pour batter over pineapple and cherries, you may have about 1/4 cup left over batter that does not fit into pan.
Bake 50 to 55 minutes or until toothpick inserted in center comes out clean. Immediately place heatproof serving plate upside down over pan; turn plate and pan over. Leave pan over cake a few minutes so brown sugar mixture can drizzle over cake; remove pan. Serve warm (would be wonderful with vanilla ice cream) or allow to cool to place on top of cheesecake.
Cheesecake
3 (8 oz.) packages cream cheese, softened
2 (14 oz.) cans sweetened condensed milk
3 large eggs
1/2 teaspoon rum extract
Heat oven to 350ºF.
Beat cream cheese in large bowl until fluffy. Gradually beat in sweetened condensed milk until smooth. Add eggs, one at a time, and extract; mix well. Place an 8.5-inch or 9-inch springform pan on top of cookie sheet, incase a small amount of batter leaks. Pour batter into pan. Place in oven, with the pan still on top of cookie sheet.
Bake 45-50 minutes or until center is set. The center should jiggle around but not look wet. Remove from oven. Cool 1 hour. Chill at least 4 hours.
Finish by using 5 spatulas (and some friends) to help you lift pineapple upside down cake on top of cheesecake