Pineapple Upside Down Cake (1950’s Inspired Recipe)

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 Pineapple Upside Down Cake hit peak popularity in the 1950’s, and is just as pretty as it is easy to make. This version of the classic dessert is made from scratch and features a light and tender white cake topped with a caramelized sugar topping, canned pineapple slices, and maraschino cherries.

When envisioning vintage desserts it is hard not to think about a Pineapple Upside Down Cake. The classic cake has not lost any of its appeal.  And it is easy to see why; the cake requires no special kitchen tools, it is absolutely dead simple to make, and when the cake is inverted onto the serving platter presentation is really quite impressive.

Upside down cakes have a long history, dating all the way back to the middle ages, but pineapple upside down cake came into its own more recently.

In 1925, the Hawaiian Pineapple Company (which would later go on to be Dole) sponsored a contest calling for pineapple recipes. The top 100 recipes were promised a $50 prize, and would also be printed in a cookbook.  The contest was judged with notables from the Fannie Farmer’s School, Good Housekeeping, and McCall’s Magazine. It is said that 2,500 of the 60,000 submissions were recipes for pineapple upside-down cake. The company decided to ride the wave of the pineapple upside down cake trend and run an ad about the flood of pineapple upside-down cake recipes it had received, and the cake’s popularity only increased! Making pineapple upside down

Vintage Dole Advertisment the Reads "Ideas for Homemakers" featuring images of pineapple desserts

Pineapple upside-down cakes began appearing in magazines, cookbooks, and advertisements fairly regularly. The Island Fever that swept over America in the 1950’s and 60’s can probably be credited to a certain extent to the Pineapple Upside Down Cake ‘s rise to peak popularity during that time period.

It seems there are two types of pineapple upside down cakes; Those that have a dense almost biscuit-like cake, and a lighter and fluffier cake version, typical of the results you would get if you used a cake box mix.

Pineapple Upside Down Cakes hit peak popularity around the same time boxed cake mixes, and many home cooks adapted their recipe to utilize the convenience of a boxed cake mix, and pineapple upside down cake made with a boxed mix is just how some families know and love pineapple upside down cake.

Overhead picture of Pineapple Upside Down Cake

And honestly, up until recently the bulk of my pineapple upside down cake making, included a box of Pineapple Supreme Cake Mix.

But, I wanted a cake made from scratch that would be moist and enjoyable to fans of the fluffier cake version but would have more “made from scratch” characteristics.

This cake is adapted from a recipe I found on Delish, this Pineapple Upside-Down Cake is super easy to make, and the end product is very pretty. I like to really go all out with the maraschino cherries, I feel like the bright red jewel tones add the vintage charm of this cake, but if you prefer you dessert to not have red dye, there are a few companies that make maraschino cherries that are free of artificial colors, dyes or flavors, or if you totally want to skip the cherries you can replace them with pecans.

Pineapple Upside Down Cake

This sweet retro dessert hit peak popularity in the 1950's, and is just as pretty as it is easy to make. This version of the classic cake is made from scratch and features a light and tender white cake topped with canned pineapple slices and maraschino cherries. 

Course Dessert
Cuisine American
Prep Time 30 minutes
Cook Time 48 minutes
Total Time 1 hour 18 minutes
Servings 8 servings
Calories 514 kcal



  • 1/4 cup unsalted butter, melted
  • 1/2 cup packed light brown sugar
  • sliced pineapple 6-8 canned slices or use fresh
  • 15-20 maraschino cherries


  • 1 and 3/4 cups cake flour sifted
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1/2 cup unsalted butter, melted
  • 3/4 cup packed light brown sugar
  • 1/4 cup granulated sugar
  • 1 large egg room temperature preferred
  • 1/4 cup sour cream
  • 1/2 cup milk
  • 1/4 cup pineapple juice (reserved from the canned pineapple or use fresh)
  • 1 Tablespoon vanilla extract



  1. Preheat oven to 350°F (177°C).

Prepare topping first:

  1.  Place 1/4 cup of melted butter into a 9x2 inch (deep dish) round cake pan. Sprinkle with 1/2 cup of brown sugar. Top with pineapple slices and arrange cherries between the pineapple slices. Set aside.

Prepare the cake

  1. In a medium bowl, mix together flour, baking powder, baking soda, and salt. Set aside. In a large microwave-safe bowl, melt butter in the microwave. Whisk in the sugars vigorously getting out any brown sugar lumps - mixture will be gritty. Whisk in egg, sour cream, milk, pineapple juice, and vanilla extract until combined. Slowly mix in dry ingredients until no lumps remain. Batter will be thick.

  2. Pour/spoon batter into prepared pan. Make sure it's not overflowing-- this recipe makes enough batter for a deep dish pan. If you find there is too much batter, make a couple cupcakes (20 minutes bake time) on the side. Bake for at 40-48 minutes. Cover loosely with aluminum foil at the 20-minute mark to avoid over-browning. Allow to cool for 10 minutes.

  3. Invert cake on top of a cake stand or a large serving plate. Slice and serve warm, room temperature, or even cold. Pineapple upside down cake is traditionally served with whipped cream - it's a delicious combination. 

  4. To Store: Cover cake and store for up to 3 days in the refrigerator.


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