I used to make this cake a ton when I was in my 20"s..my first husband absolutely loved pineapple anything, this cake, pineapple pie, fresh pineapple, anything with it in it, but after he passed away for some reason I kind of quit making it. My sister, Yvonne, made a big one last Sunday and posted it on Facebook and it brought back to me how yummy it was, especially loaded with topping of some type..fresh whipped cream is the best, but I also like Cool Whip on this cake and that's what we will be using tonight since I don't have whipping cream in the house and am not in the mood to go to the store today. I happened to have a can of pineapple rings and maraschino cherries in the cupboard..luck was on my side. This is the recipe I used to use and since it's tried and true (I used to double it for a 9 x 11 pan) I made it (in an 8 x 8) since it's just me and Dave this weekend. It's from an old edition of the Better Homes and Garden's cookbook..I think my first cookbook..about 1970-1971.
PINEAPPLE UPSIDE DOWN CAKE:
1 (8-1/2) ounce can sliced pineapple (rings)
3 Tablespoons butter softened
1/2 cup brown sugar
1/3 cup shortening (I use Crisco)
1/2 cup granulated sugar
1 teaspoon vanilla
1 cup sifted all purpose flour
1-1/4 teaspoons baking powder
1/4 teaspoon salt
Drain pineapple, reserving syrup. Melt butter in an 8 x 8 x 2 inch baking pan. (I just set the baking pan on a stovetop burner to melt the butter, don't scorch it though) Add brown sugar and 1 Tablespoon of the pineapple syrup. Add water if needed to the rest of the syrup so it equals 1/2 cup of syrup. Arrange pineapple in the bottom of the pan. Place a cherry inside rings or spaces. set aside.
Cream together shortening and sugar until light and well mixed. Add egg and vanilla. Beat till fluffy. Sift together dry ingredients; add alternately with the 1/2 cup reserved pineapple syrup, beating after each addition until smooth. drop globs on top of base you set aside and smooth out so completely covering pineapple base. Bake at 350 degrees for 40-45 minutes. Cool 5 minutes ; invert on plate. Serve warm.