Summer Comfort: Pineapple Upside Down Cake

pineapple upside down cake

My husband has never been a dessert eater. He would eat pretty much anything else on creation, including appalling inventions that he somehow Frankensteins together in the kitchen when no one else is around, but I had almost never seen the man touch a dessert plate. Until I made Pineapple Upside Down Cake, that is.

I never grew up eating Pineapple Upside Down Cake on a regular basis, as it never made it to my family’s regular rotation, but I remember my Aunt Amy making a giant cake of it when I was around seven, and me thinking, “where has this been all my life?”  Despite this epiphany, I slugged through high school and college without a hint of this cake, and then happily rediscovered it once I had my kids.  It was last Fourth of July, and I was looking to flex my newly discovered cooking skills, but kids in tow limited me to something not-too-crazy.  I Googled quickly for an easy dessert, and there it came, Pineapple Upside Down Cake.

My husband reluctantly tried it, the dessert hater that he is, but was totally flabbergasted at how delicious this was.  His only quip was that my son ate all of the cherries off of the cake, which did happen in a late night refrigerator sneak.

My only pet peeve with the traditional versions of this cake was the limited amount of pineapple and cherries per piece, which I quickly remedied by cutting the pineapple slices in half and creating a fan effect with the pineapples and cherries.  If you’ve never been lucky enough to try this cake, the brown sugar and butter topping melts into the pineapples and cherries to create a delicious syrupy topping that perfectly compliments a classic yellow cake.

This is such a retro dish, but still totally relevant and undeniably addictive.  Serve this with some Cuban coffee, and you’ve got a great cake for dinner party dessert.

 

Print Recipe
Pineapple Upside Down Cake
This is a wonderful traditional dish that is great for company or just one of those days when you need something sweet. While the cake is typically done using full pineapple rounds, I cut them in half to increase the pineapple distribution, because who doesn't need more pineapple in their life?
pineapple upside down cake
Course Dessert
Cuisine American, Cuban
Prep Time 20 minutes
Cook Time 50 minutes
Servings
9" cake
Ingredients
Pineapple Topping
Cake (Adapted from Smitten Kitchen)
Course Dessert
Cuisine American, Cuban
Prep Time 20 minutes
Cook Time 50 minutes
Servings
9" cake
Ingredients
Pineapple Topping
Cake (Adapted from Smitten Kitchen)
pineapple upside down cake
Instructions
  1. Preheat your oven to 350 degrees.
  2. Take the pineapples out of the can and slice them in half carefully.
    slice pineapple
  3. To make the batter, sift together the dry ingredients in a bowl. In a separate, large bowl, beat the butter and the sugar until the mixture becomes pale and fluffy. Add the vanilla and eggs to this mixture. Beat in buttermilk until just combined. Add flour mixture small batches, mixing until each addition is just incorporated.
    final cake batter
  4. Place unmelted butter in cake pan and place the pan with the butter in the oven to melt. (This just saves you a dish, which I always appreciate)
  5. Once the butter is melted, take both pans out of the oven, and sprinkle 1 cup of brown sugar over the melted butter in each pan.
  6. Add pineapples in a fan like pattern until they fill the pan, and then add one cherry per pineapple hole.
  7. Once the pineapple design is set, pour half of the cake batter into each pan, until it fills the cake pan up 3/4. You may have extra cake batter.
  8. Place both cakes in the oven, and bake for about 50 minutes, or until a knife or fork comes out clean.
  9. Once cooled enough for you to handle the pans, cover one cake with a plate and invert the cake pan so that the cake falls on the plate with the pineapples on top.
  10. Serve and enjoy!
    pineapple upside down cake
Recipe Notes

You can use a box yellow cake mix for the cake batter if you are short on time or energy. I won't tell anyone and it still tastes great.

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