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Heloise Chocolate Pineapple Upside Down Cake


Heloise Chocolate Pineapple Upside Down Cake

This is a cake I have made "my own" because I love the taste of the chocolate and the pineapple. It is really rich, sinful and worth the extra calories. Just don't eat the whole thing alone! I made this in college and it would last only an hour or so!

Here is my ad-hoc recipe!


  • 1 box dark-chocolate cake mix
  • 1 cup dark brown sugar
  • 1/2 cup butter
  • 1 can crushed pineapple, drained
  • 1 can pineapple rings, drained
  • 1 jar of red (or green for the holidays) maraschino cherries.
  • Chopped macadamia nuts, pecans or walnuts.

Note: I lived in Hawaii as a child and loved Hawaiian macadamia nuts! However, as yummy, melt-in-your-mouth and buttery tasting as they are, they are also the highest fat (monounsaturated) nut on earth! One half cup equals about 481 calories, and 425 of those are from fat and that’s 51 grams of fat! Just a note from a gal who watches her fat intake.

* You can put chopped pecans or walnuts over the brown sugar.


I make this like my mother did—in a cast iron skillet. You can use a baking dish, choose the size stated on the box of cake mix. Make the cake according to the directions on the box.

1. Put the skillet on the stove and slightly melt the butter. Or, if you use a glass baking dish, turn the heat on low ONLY on a gas stove or melt the butter in your microwave. Note: Glass baking dishes are not designed to be placed directly on an electric heat element.

2. Pour in the brown sugar mix to moisten, and gently press, so the bottom is all covered.
*Add chopped nuts, if desired.

3. Place the pineapple rings around the skillet, or in the baking dish. Put a cherry in the middle of each pineapple ring, extras on the side.

4. Pour the DRAINED, crushed pineapple over the brown sugar, pineapple rings and cherries.

5. Carefully pour the prepared chocolate cake batter in the skillet or baking dish.

6. Bake according to the box directions, or until a knife inserted in the center of the cake comes out clean.

7. Remove from the oven when done, run a knife around the edges of the skillet or baking dish. Use a heat safe plate or serving platter. Carefully turn the cake upside down on the serving dish. Shake the skillet to loosen the brown sugar and then slowly remove the skillet or baking dish.

If there is "good goop" still on the bottom of the skillet, use a knife to scrape it off and add to the cake.

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