This was my husband's Mom's favorite Pineapple Upsidedown Cake. I've been making it for years although I've tweaked it a little. She baked hers in an iron skillet. I bake mine in 9 inch round cake pans. Still really good! Enjoy!
Melt the butter in a pan. Add the brown sugar and stir until melted. Pour into iron skillet or baking pan.
Beat egg until light. Add sugar and beat well. Mix the flour and baking powder. Alternately, add flour mixture and milk to the egg/sugar mixture. Beat well and add shortening and vanilla.
Arrange the pineapple slices over the brown sugar/butter mixture in the pan. Place a cherry in the middle of each slice. Pour batter evenly over the pineapple. Bake in a 350 degree oven for 30 minutes.
Immediately turn the cake onto a plate. Spoon any "sauce" that remains in the pan over the cake.