Retro Pineapple Upside Down Cake

Pineapple Upside Down Cake

This vintage inspiration for Retro Pineapple Upside Down Cake comes from my 1976 Better Homes & Garden New Cook Book. This is a classic retro cake inverted upside down. It has a rich, buttery brown sugar soaked pineapple mixture over a light sponge cake with a pop of red from maraschino cherries.

Vintage inspired recipe baked it modern:

  • added oil in addition to the butter to keep it moist
  • added more salt which our modern palettes are accustomed to
  • doubled the recipe
  • added rum to boost flavor
  • used a 9×13 pan instead of a 8×8 square
  • swapped out the syrup and water mixture and used buttermilk

Baker’s tips for Retro Pineapple Upside Down Cake:

Use both butter and oil for a tender cake:

Using butter in a cake provides flavor, while adding oil makes it super moist. So even if your cake recipe calls for just butter or just oil, you can combine them together to maintain the flavor from butter and use some oil to keep the texture of baked goods moist. Be sure to use an oil that is has a neutral and light flavor like canola oil or extra light virgin olive oil.

Canned vs. fresh pineapple in baked goods:

The recipe calls for canned pineapple in syrup as that was popular during that time. It also referred to steps such as using part of the syrup in the pineapple mixture and saving a portion of it mixing it with water and using in the batter. However, I used canned pineapple in 100% juice, so it didn’t make the cake too sweet. Drain the juice and measure it out before adding to the batter. Although you may want to use real pineapple, I found out after testing the recipe, not to do so. Reason being, is that fresh pineapple contains enzymes that change texture when baked. During this process, the pineapple releases too much liquid and making the cake soggy.

Buttermilk or sour cream yields a tender cake:

For a light, moist tender crumb in cakes, add buttermilk or sour cream. If you don’t have buttermilk, simply make it by placing 1 1/2 tsp. of white vinegar into a liquid measuring cup and add milk to the 1/2 cup line. Dry buttermilk is good to keep on hand in your pantry to mix up as needed.

baking sheet:

An aluminum, 9×13 is the best cake pan to use for this cake because it helps conduct even heat. My favorite brand of cake pans are Fat Daddio’s or Nordic Ware or a glass 9×13 pan. I wanted to keep this cake traditional, however, you could always try different sizes of pans as well such as round or even a bundt pan lining the pineapple slices up and around the sides.


  • Mixer with paddle attachment
  • strainer
  • measuring cups & spoons
  • liquid measuring cup
  • off-set spatula
  • 9×13 baking pan

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