Heirloom Pineapple Upside Down Cake

Total Time
Prep 30 mins
Cook 30 mins

I have been making this recipe for 25+ years but it is actually from the 1920's. This is an unusual cake and should be cooked in a cast iron skillet. The batter isn't like an angel food cake, at all. It is crunchy on the outside but chewy. Not light and fluffy like most people are used to. And it is very beautiful. And very rich.

Ingredients Nutrition


  1. Preheat oven to 350.
  2. Melt butter in bottom of a 9 or 10 inch cast iron skillet by either placing it in the oven or melting on the stove top over low heat. Don't let it brown.
  3. Cover melted butter with brown sugar spreading in an even layer.
  4. Put one slice of drained pineapple in the center and cut the other rings in half. Arrange the rest of the pineapple halves like a spoked wheel -- rounded edges facing the same way. You may have a few unused pieces.
  5. Fill spaces with nuts and candied cherries if you have them. (The cherries are pretty and I use them when I have them. The walnuts I think are great in this recipe so use them unless there is an allergy problem.).
  6. Make batter as directed below and pour over all.
  7. Bake for about 30 minutes, then check every five minutes until a toothpick inserted in the center comes out clean.
  8. When done, run a knife around the edge to separate cake well from the edge of the skillet. Very important. You do not want that cake to stick when you try to flip it over.
  9. Let cool for a few minutes (just a few -- the cake can't set and cool or it will "glue" itself to the pan) so the syrup isn't like molten lava. While wearing kitchen mitts and long sleeves, (this stuff is hot and you do NOT want to splash any on you) place a large plate on top of the skillet and then in one smooth motion invert skillet and dump cake onto the plate.
  10. Allow to cool for about an hour and serve very warm.
  11. Make batter-------------------------------.
  12. Beat 4 egg yolks and sugar and pineapple juice until light.
  13. Sift flour and baking powder and fold into the egg/sugar mixture 1/3 cup at a time.
  14. Fold in 4 stiffly beaten egg whites.
Most Helpful

Thanks to Kat's Mom for starting the Alphabet threads and to Potsie for posting this amazing cake! It turned out flawlessly and lasted 20 minutes with 4 adults having two pieces each! Below are my notes on my experience with making it. 1) Have everything ready before you melt the butter. That way, the batter will adhere to the hot butter/sugar/pineapple mixture and integrate into the batter. 2) Use the melted butter to "grease" the sides of your skillet. The cake comes out without a hitch. 3) RESERVE THAT PINEAPPLE JUICE! When I tried to mix the yolks and sugar, there was too little liquid from the eggs to mix them. I added 2 tablespoons of pineapple juice to make the egg/sugar mixture fluid enough to pour. 4) I reduced the 2 cups of brown sugar to 1.5 cups, like Nsremom suggested. It was the perfect amount; not too sweet. 5) The cake puffs up like a souffle. It drops after coming out of the oven. Mine was done at 25 minutes so check earlier so it doesn't burn. Allow to sit for 5 minutes, and then turn out from the skillet. Since making this, two of my other friends have wanted the recipe. It's worth every second it takes to bake it. BEST version of this cake that I've ever eaten!!!

The_Swedish_Chef March 30, 2009

On the one hand, it's fantastic that Sushiman is an excellent shopper. On the other hand, control freak that he is, we go shopping together so we buy the "right" things. One the one hand, he's got the magic feel for getting bargains. On the other hand, it's not a bargain if you end up never using the stuff. On the one hand, he found some canned pineapple rings at the most amazing price. On the other hand, they've been taking up space in the kitchen cabinet since May. Enter this recipe, a perfect solution for my dilemna. I followed the recipe almost to a tee, using the candied cherries but substituting candied pecans for the walnuts (we just LURVE those candied pecans). I didn't use a cast iron pan, I used a silicon cake pan and I think that even with waiting longer than the recommended "few minutes" for the cake to cool, it popped out of the pan beautifully. The cake was a major hit for dessert, with a scoop of homemade vanilla ice cream on the side. On the one hand, it was delicious. On the other hand, I might as well just spread this stuff directly on to my hips.

Mirj November 14, 2006

Delicious and so fattening.....wow...I about freaked putting the 1/2 C of butter in, THEN adding the 2 cups of brown sugar....I chickened out and only put 1.5 cups of b sugar in. Don't attempt this recipe while dieting.

Nsremom July 01, 2008