Pineapple upside down cake recipe

The other day, while mindlessly surfing the net, I ran across a compilation of the ugliest, most disgusting retro recipes. You know, such fine delicacies as hollandaise covered bananas or a pie made of tuna and jello. After I stopped uncontrollably convulsing, I got to thinking about what vintage recipes have stood the test of time due to their undeniable deliciousness. And yes, as you may have guessed, pineapple upside down cake came to mind.


Traditionally made in a cast iron skillet, this classic favorite features a brown sugar caramel soaked cake with rings of tender pineapple and maraschino cherries. I’m drooling already. In the spirit of all foods that are sinful, I decided to make my own and jazz it up a little bit. My version is made with fresh pineapple, a whipped cream cheese frosting, and a bit of toasted coconut. I mean, who doesn’t love pineapple and coconut together?

I will warn you, however, this cake is a labor of love. It will take good bit of time to prepare. But once you run your fork through the tender cake, have a bite, and lick the rich frosting off your lips, you’ll know it was so worth it. For more bang for your buck, you could try preparing 2 at once. I’m sure you owe someone big, and who cold think of a better repayment?

So take the time to make this right and you won’t regret it. Just think about how much social media attention you’re going to get after you post a pic of one of these bad boys. So preheat your oven and let’s get baking!


Ultimate Rich and Decadent Pineapple Upside Down Cake

Yield: 8 servings

Prep Time:40 minutes

Cook Time:40 minutes

Total Time: 1 hour and 20 minutes



For the cake:

  • 1 1/2 cups all-purpose flour
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 6 tablespoons unsalted butter, softened
  • 3/4 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla
  • 1/2 cup unsweetened pineapple juice


For the Pineapple and Cherries:

  • 6 tablespoons unsalted butter, melted
  • 1/2 cup packed light brown sugar
  • 1/2 medium pineapple, peeled, quartered lengthwise, and cored
  • 1/2 cup maraschino cherries


Toasted Coconut:

  • 1/4 cup shredded coconut


For the Frosting:

  • 1/2 (8 ounce) package cream cheese, softened
  • 1/4 cup sugar
  • 1 teaspoon vanilla extract
  • 1 cup heavy cream, well chilled




Get the Cake Batter Started

Preheat your oven to 350ºF.

In a medium bowl, sift together the flour, baking powder, and salt. Set aside. In a large bowl, beat together the butter and sugar on high speed with an electric mixer until light and fluffy, at least 3 minutes but the longer the better. Add your eggs to the butter-sugar mixture, one at a time, until fully incorporated. Pour in the vanilla and pineapple juice and continue mixing until well combined. Set aside.


Arrange the Pineapple

Pour the melted butter in the bottom of a 9-inch cake pan. Using a brush or your fingers, spread the butter up the sides of the pan, then sprinkle on the brown sugar. Arrange the pineapple and cherries in the bottom of the pan however you like. Make a portrait of the Virgen de Guadalupe for all I care. Now cake batter.


Pour on the Batter

Add the dry flour mixture to the wet egg and butter mixture, just until combined. No over mixing please! Spoon the batter over your arranged fruit and smooth out with a spatula until even. Bake in the oven until an inserted toothpick comes out clean, about 40 minutes. Set aside to cool for 10 minutes, but no longer or the fruit might just separate from your cake.  Run a knife around the edge to loosen and flip out onto a rack to cool to room temperature.


Toast the Coconut

In the meantime, make the toasted coconut. Reduce the oven temperature to 325ºF. Spread coconut on a baking sheet. Bake, stirring every 2 minutes, until the coconut becomes browned and smells amazing, about 10 minutes. Keep a good eye on this stuff, it goes from white as snow to burnt as hell in no time flat. Allow to cool thoroughly.


Make the Frosting

Now, make the frosting. Place the softened cream cheese in a large bowl. Beat with an electric mixer until fluffy, then add the sugar and vanilla until well combined. With the mixer running on a high speed, slowly pour the cream into the cream cheese mixture until incorporated. Scrape down the bowl, then continue whipping until medium peaks form.


Frost and Eat!

Using and offset spatula or butter knife, frost the sides of the cooled cake, leaving your beautiful artwork on the top of the cake untouched. Carefully press the toasted coconut to the sides of the cake. Display your beautiful cake for all to see or devour immediately.



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Since I was a little girl, I've been all about food. As a 7 year old, my first half-baked attempt at chocolate cake was comprised of scrambled eggs and chocolate milk powder microwaved, then topped off with Red Hots. I've come a long way since then. I've been lucky enough to get to work in restaurants for 10 years and graduate from one of the best culinary schools in the country. At the moment I'm enjoying working with a killer food photographer while doing freelance food styling and writing. I'm always excited thinking about what my next culinary adventure will bring. Who knows, maybe I'll revisit that chocolate cake with Red Hots.
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