Pineapple Upside-Down Cake


1/3 cup butter
1/3 cup dark brown sugar
1 tablespoon black rum
1 tablespoon light corn syrup

20 oz canned pineapple rings in 100% pineapple juice, drain and reserve juice for batter
maraschino cherries*

1 1/2 cups flour**
1 cup sugar
1/3 cup butter, at room temperature
1 teaspoon vanilla paste
2 eggs, at room temperature
2 tablespoons black rum
1/2 cup pineapple juice (from canned pineapple rings)
1 teaspoon cardamom
2 teaspoons baking powder
pinch sea salt

Preheat oven to 350. Butter or spray (with cooking spray with flour) a 9-10 inch springform pan***. Arrange pineapple rings on the bottom of the pan. Add a maraschino cherry to the center of each ring. Set aside.

In a small saucepan, melt and stir together butter, brown sugar, rum and corn syrup. Cook over low heat about 5 minutes or until it thickens slightly. Stir thoroughly to combine. Pour over the pineapple rings. Set aside.

Cream together the softened butter and sugar in a large bowl. Add the eggs and vanilla paste and beat until flour. Whisk together the spices, baking powder and flour in a medium bowl. Whisk together the pineapple juice and rum. Add the dry ingredients alternately with the pineapple juice mixture beginning and ending with the dry ingredients. Pour into the pineapple and caramel laden cake pan and bake 45 minutes or until a toothpick inserted in the center comes out clean. Allow to cool in pan 5 minutes then invert onto a plate. Cool completely, on the plate, over a wire rack.

*If you can find them, Luxardo Maraschino Cherries are well worth the extra price. They are miles away from the syrupy, garishly red cherries found in the supermarket for $1.50.

**I used White Lily flour which, while not quite cake flour, is slightly lighter than all-purpose.

***Traditionally, pineapple upside-down cakes are made in cast iron skillets. I don’t have have a 10-inch skillet (and my 12- and 14-inch skillets seemed too big) so I used a springform pan, which I think works just as well.

My thoughts:

Another recipe I created for our annual “decade” themed meal(s). This year it was the 1920s!

Pineapple upside down cakes exploded in popularity during the 1920s. Thanks to Dole, canned pineapple was readily available. Upside down cakes made in cast iron skillets had already been popular for many years so it made sense that when the average person had access to pineapple, they’d incorporate them. Upside down cakes are wonderful to serve because despite being relatively simple, they are impressive and cheerful looking when presented. They can also be made a day ahead of time (stored unrefrigerated) and need no icing, which is great for any last minute dessert needs. I’d think most people have all of the ingredients in their cabinets at all times. I know I do.

For this cake, I made a dark rum caramel sauce for the “topping” and used fancy maraschino cherries which taste amazing, and actually like cherries. I added a bit of cardamom to the cake as so many ’20s recipes did but much less than some recipes I’ve seen that call for 2-3 and even 4 teaspoons of cardamom. That seemed a bit much. One teaspoon is just enough, I think. If it really was the Prohibition era 1920s, I might not be able to get my hands on actual rum so feel free to sub in some good quality rum flavoring instead. The 1920s was when the use of vanilla and other extracts rose and became common place. I also used some yummy vanilla paste by Heilala Vanilla instead of extract and the cake was flecked with tiny vanilla seeds. The cake itself is simultaneously dense and light, substantial enough to hold up the topping without getting soggy (even after a number of days) but with a light crumb and flavor. I think this is because I used a lot of baking powder and it sort of rose high then gently fell during the baking process.

I have to say, this is quite possible my husband’s favorite cake of all that I’ve made over the years. He could not stop raving about it and has requested that a version of it to make an appearance at his birthday in May. It really was a pleasure to eat. I can see why they were so popular!


  1. This is my father-in-law's favorite cake – I'll bookmark this and make it for his next birthday. I have a 10-inch cast iron skillet, so I could make it in there – would that change anything? Also, can I sub extract for vanilla paste? Would the amount be the same?

  2. Nothing would change! Enjoy!

  3. Ha! I was going to ask the same about the 10" cast iron. I had a similar recipe that I made in my 10" cast iron skillet and it was divine. Can't wait to try yours!

  4. Enjoy! If you are using cast iron, just make sure it is well greased so it releases easily.

  5. I'm so tempted to make this for myself for my birthday! My favorite!!

  6. BettyAnn @Mango_Queen

    One of my most favorite cakes and a go-to when I'm in a rush to make a good dessert. This is a new recipe I'd like to try. Thanks for sharing!

  7. i love this cake going to make for my daughters

  8. Roz | La Bella Vita Cucina

    All this week as my father has been drawing his last breathes on this earth, my family has been talking about his favorite cake: pineapple upside down cake. You are a dear for preparing and posting this special old-fashioned favorite at the time of my family's loss. This is one of the best recipes on earth and I'm glad to see others who appreciate it! YUM!!!! I thank you for bringing me and my family a smile (and a 'sweet' smile') this week.

  9. Always wanted to try this now you've really inspired me to do this…

  10. Marcie @ Flavor the Moments

    There's nothing like warm, buttery, sweet, pineapple upside down cake. I've been looking for a new recipe, so it looks like I'm in the right place!

  11. Just made this for my boyfriend's birthday. We finished half already between the two of us. It is really delicious! Thank you.

  12. Oh, I'm so glad you enjoyed it!

  13. Came across your recipe purely by accident – and it brought back some wonderful memories as a young kid, fighting over who was going to get the round toffee bits from inside the pineapple rings! Going to try and surprise my wife and give your recipe a go with the cherries in the center instead! Wish me luck!