Ultimate Fresh Pineapple Upside Down Cake

Here’s another Classic!  Ultimate Fresh Pineapple Upside Down Cake!

So much caramelized yumminess, it’s insane.

Developed centuries ago, this cake has stood the test of time.  They used to be cooked in cast iron skillets over an open fire.

Fruit and sugar was added to the bottom of the skillet and cake batter was poured over the mixture.  Once cooked, flipping it over onto a plate not only released the cake from the skillet, but showed how pretty the caramelized fruit was on top.

The cake is a fluffy white vanilla cake and it’s made with fresh pineapple, brown sugar and butter for the carmelization.

But of course, if you don’t have fresh pineapple, you can absolutely use canned pineapple. I had a pineapple I bought at the grocery (ALDI) and have wanted to make this vintage recipe to put on the blog.

Finally getting to it.  There’s like a million desserts I want to make, but how could I ever leave this off the list?  I can’t…it’s the real deal.

This lovely cake deserves to be put on a pedestal.

This cake was made in an 8 inch pan.

One thing you should know.

Don’t use a springform pan.

Lesson learned when you make these types of upside down cakes.  Once things start heating up, that glorious butter brown sugar glaze is going to drip and spill in your stove and make a huge mess.

Bake it in a regular 8″ buttered cake pan to get ultimate results.

I love bringing back classics and these cakes are not as hard to make as you would think.

You basically cook the fruit with the butter and brown sugar until tender and then place it in the bottom of your pan.  Make and dollop the cake batter on top and then smooth out.  Bake away!

Leave to stand for 5 minutes then turn out onto your platter.

Serve warm or room temp.  We love fresh whipped cream with cherries with ours, but you could add a yummy scoop of vanilla ice cream and caramel topping, whipped cream and a cherry to delight in the Absolute Ultimate Fresh Pineapple Upside Down Cake treat.

Let’s Party!

You might love these cake classics too!  Super-Moist Chocolate Cake with Chocolate Buttercream Frosting, Ultimate Carrot Cake,  Streusel Coffee Cake Pound Cake  Dark Chocolate Texas Sheet Cake and this Super-Moist Vanilla Cake with Vanilla Buttercream Frosting.

Print Recipe

4.34 from 6 votes

Ultimate Fresh Pineapple Upside Down Cake

This Ultimate Fresh Pineapple Upside Down Cake has caramelized fresh pineapple basking in a rich butter brown sugar gooiness atop a fluffy vanilla cake and it's INSANE!

Servings: 12 Slices

Calories: 157kcal

Author: Kim Lange

Ingredients

Bottom of Cake:

• 2 Tablespoons brown sugar

Caramelized Pineapple:

• 3/4 cup brown sugar
• 1/2 stick unsalted butter softened
• 1 large pineapple—peeled quartered, cored and sliced 1/3 inch thick

Vanilla Cake

• 1 stick (1/2 cup) unsalted butter very softened
• 3/4 cup granulated sugar
• 1/2 cup Greek yogurt or sour cream divided
• 2 large eggs
• 1 teaspoon vanilla extract
• 1 1/4 cups all-purpose flour
• 1/2 teaspoon baking powder
• 1/4 teaspoon baking soda
• 1/2 teaspoon salt

Instructions

• Pan Preparation:
• Preheat the oven to 350°.
• Butter an deep dish 8-inch round cake pan. Sprinkle the bottom with 2 tablespoons of the brown sugar.

Carmelized Pineapple:

• In a large skillet, combine 3/4 cup of brown sugar with 1/2 stick of butter and cook over moderately low heat until the butter is melted. Add the pineapple and cook over moderately low heat, stirring occasionally, about 20 minutes or pineapple is tender. Using a slotted spoon, arrange the slices in the cake pan, overlapping them if necessary, then pour the pan juices over the pineapple, set aside.

Vanilla Cake:

• In a medium bowl, whisk together the flour baking powder, baking soda and salt, set aside.
• In a large bowl, whisk together yogurt, eggs, vanilla, set aside.

  Using mixer, mix together the softened butter and sugar for 2 minutes on medium speed and then add in the yogurt/egg mixture and mix together.

  Add flour mixture to the yogurt mixture and mix just until combined and no lumps appear.
• Spoon the batter over the pineapple and spread it evenly.
• Bake for about 40 minutes, until the cake is deep golden. Let cool for 5 minutes on a rack. Run a knife around the edge of the cake, invert it onto a plate and remove the pan.
• Replace any pineapple that may have stuck to the pan. Serve warm or at room temperature.