Julian does a great job of keeping me on track with this blog. He’s constantly worried when I don’t post my regular two posts a week, and always makes sure to remind me that I haven’t posted a “Classics” or “Cheers to the Weekend” post in a while. He’ll throw some ideas my way every now and then and sometimes they’re good and sometimes they’re a little out there. Much was the case this time around with “The Classics” segment. He wasted no time in telling me that I haven’t posted one in a bit. I think the last time I shared a classics recipe was this Churros with Chocolate Dipping Sauce post. That was last year, so I had to make sure to fix this right away. Since Julian keeps me going, I thought I’d finally make his favorite cake. So I’m dedicating this Pineapple Upside-Down to him. He’s been asking me to make it for a while now and I just kept saying okay, but never actually made it. They say good things come to those who wait, so it’s a good thing for all of us that Julian had to wait an eternity for this cake. It’s really good.
I started the classics segment a while ago, the first one being this Buttermilk Fried Chicken, because I wanted to share simple and straight forward recipes on my blog. I wouldn’t say that my recipes are hard or complicated, but some do involve a bit more time than others. There are certain recipes that we should all know how to make because they’re delicious, dependable, and easy to whip up. Those are the recipes that I want us all to have under our sleeves for when we’re in need of something fast and reliable. Sometimes simple really is best. Let’s keep that in mind moving forward. I think it’s sometimes so easy to forget that, especially in this day and age. Happy Baking!
Let’s start by making the cake batter for this upside-down cake. The first thing we have to do is whisk or sift the dry ingredients together. In a large bowl, combine the flour, baking powder, and salt. Set aside.
**Note: I’m not an avid fan of sifting, out of pure laziness. So I just whisk everything together, but if you’re a sifter at heart, then by all means sift away!**In the bowl of a stand mixer, beat the butter until fluffy. Then slowly stream in the granulated sugar, and beat on high until light and fluffy, about 5 to 8 minutes. Stir in the vanilla and vinegar. Then add the eggs, one at a time, beating well after each addition.
**Note: The vinegar helps balance the sweet and tart flavors in the cake and helps combine everything well. I know it sounds weird, but don’t omit it. It’s like adding salt to desserts. It’s all about creating balance.**Once the eggs have been added, stir in 2 tablespoons pineapple juice from the canned pineapple slices. Stir until well combined. The mixture might look curdled at this point, but that’s okay. Then add the dry ingredients alternately with the buttermilk, starting and ending with the dry ingredients, making sure to mix until just combined. Do not over mix at this point.
Set the batter off to the side and then turn your attention the to topping. Set a 10-inch cast iron skillet over medium-high heat along with the remaining butter. Once melted, whisk in the vanilla, brown sugar, and brandy. Cook until dissolved, constantly stirring, about 1 minute.Remove the skillet from the heat and then place the pineapple slices into the caramel in an even layer. Then arrange the cherries, placing one into the center of each slice and around the edges of the pan. Side Note: If you don’t have a cast iron skillet, you can make the caramel topping in a pot and the pour it into a 10-inch round cake pan with high sides. Then arrange the fruit on top. Pour the batter over the top of the fruit and caramel, making sure to pour it evenly over the top to completely cover it. Please note that the batter with be slightly more thin than you might be used to for upside-down cakes, but have no fear it will be great. I promise. Bake until the cake is golden brown, set and a toothpick inserted in the middle comes out clean, about 30 to 35 minutes. Remove from the oven and let cool in the skillet for about 10 minutes. Then place a large platter or plate over the skillet and carefully flip it over. Let the cake sit like that, upside-down, for 10 minutes longer. Remove the skillet, the cake should come out clean from the pan.
**Note: If for any reason any fruit is stuck to the bottom of the skillet, just lift it out with a spatula or fork and place it on the cake.**Spoon any of the remaining sauce in the skillet over the cake. Then cut and serve, either warm or at room temperature. I prefer the cake slightly warm, but either way would be great! Although this was my first venture in pineapple upside-down cake, I’m no stranger to upside-down desserts. If you remember, these Chocolate Chip Banana Upside-Down Muffins from a little bit ago were my first upside-down venture and they are irresistible.
If you want to switch things up a bit from the classic route, try adding shredded coconut to the batter or even chopped nuts like walnuts or pecans. That would really pump up the volume on this cake. I’m not a fan of coconut, so that’s why I didn’t add any BUT if you are, it would be a nice addition. Any leftovers, if there are any leftovers, can be stored in the fridge wrapped well in plastic for up to 3 days. You can then leave it out and allow it to get to room temperature or warm it up very briefly in the microwave to get the chill off.
**Note: Although you can store any leftovers, this cake is really best when eaten the day you make it. I recommend making it early on before you plan on serving it for a dinner party and then force your guests to eat it all.**If you make this recipe, along with any other recipe from the site, be sure to snap a picture and share it on Instagram or Facebook and tag me and hashtag it with #CandidAppetite or #TheCandidAppetite. Once you start making these Classics recipes, be sure to also tag it with #TCAclassics! I’ll be monitoring it all closely and share my favorites throughout! Happy Cooking!
- 1¾ cup all-purpose flour
- 2 teaspoons baking powder
- ¼ teaspoon salt
- 1⅓ cups unsalted butter, divided
- 1 cup granulated sugar
- 1 tablespoon distilled white vinegar
- 3 teaspoons vanilla extract, divided
- 3 large eggs
- 2 tablespoons pineapple juice (from the sliced pineapples)
- 1⅓ cups buttermilk
- ½ cup plus 2 tablespoons light-brown sugar
- 2 tablespoons brandy or rum
- 7 slices canned pineapple (from a 20-oz can)
- ½ cup maraschino cherries
- Preheat oven to 350 degrees F.
- To make the cake, in a large bowl whisk or sift together the flour, baking powder, and salt. Set aside.
- In the bowl of a stand mixer, beat ¾ cup butter until light, about 3 minutes. While the mixer is running, slowly stream in the sugar and beat on high until light and fluffy, about 5 to 8 minutes. Stir in the vinegar and 2 teaspoons vanilla extract. Add the eggs, one at a time, mixing well after each addition. Make sure to scrape the sides and bottom of the bowl with a rubber spatula as needed. Stir in the pineapple juice and mix until evenly incorporated. The mixture might look curdled after you've added the pineapple juice, but that's okay. Add the dry ingredients alternately with the buttermilk, starting and ending with the dry ingredients until well combined. The batter will by slightly thinner than you're used to. Set aside.
- To make the topping, set a 10-inch cast iron skillet over medium-high heat along with the remaining butter. Once melted, whisk in the remaining vanilla, brown sugar, and brandy and cook until dissolved, about 1 minute. Remove from the heat and arrange the pineapple slices into the caramel in an even layer. Arrange the cherries among the pineapple slices, placing some in the middle of the rings and around the outside. Pour the cake batter evenly over the fruit and caramel. Place the skillet over a baking sheet, to catch any drips. Bake until cake is golden brown and set, and a toothpick inserted in the middle comes out clean, about 30 to 35 minutes. Let cook for 10 minutes and then place a large plate or platter over the skillet. Carefully flip it over and let the cake sit upside down for 15 minutes and then lift up the skillet. The cake should invert perfectly. Serve warm or at room temperature. Any leftovers can be wrapped well and stored in the fridge for up to 3 days. Enjoy!