Pineapple Upside-down cake is my all-time favorite cake. I made it back in the day for my hubby when we were dating while my parents still had their house in Murrieta, from that moment on I think that is when he knew he could marry me. I recipe I had always made was my great-Grandma’s and my Mom (if she would ever comment to correct me) would probably tell you that it goes back further than that. That recipe (which I do not have to share, because it’s at my parents) is made in a cask iron skillet, you warm the sugar/butter mixture in the skillet getting it all hot and bubbly and then you add in the batter which instantly gives it a crunchy caramel crust, which is why I love this given cake. Baking this cake as cupcakes gets a little trickier and it’s harder to achieve the caramel crust because it’s the cask iron that really achieves that end product. I have made these cupcakes once before here using store-bought cake mix and they were okay. Honestly, the best part about this cake is the sugary topping and caramelized pineapple, well, in my opinion. So, if your stretched for time you can totally use a cake mix but simply mixing some flour and baking powder is almost easier and cheaper. For today’s version, I made them for girl’s game night at my girlfriend Janelle’s house. While I wish I would have used more topping in each well it would have made a bigger mess in my oven so I am glad I stuck to one teaspoon. So with that said, here is the recipe I used today and I promise one day I will share the recipe that won over my husbands heart and tummy.

Pineapple Upside Down Cupcakes.
Makes 24

Topping:
3/4 cup butter
1 cup dark brown sugar (I actually used light)
2 tbsp dark rum (optional, I did not use it because I couldn’t reach that high into my pantry)
1 20 oz can canned pineapple tidbits in pineapple juice (drain and reserve juice for batter)
12 Maraschino cherries, halved.

Cake Batter:
¾ cup sugar
¾ cup butter, at room temperature
3 cups all purpose flour
3 large eggs, at room temperature
1 ½ cup pineapple juice
4 ½ teaspoons baking powder
3 teaspoons vanilla

Directions:

Preheat oven to 350. Spray cupcake tins with cooking spray. In a small saucepan, melt and stir together butter and brown sugar. Cook over low heat about 5 minutes or until it thickens slightly. Add in rum. Stir thoroughly to combine. Pour about two teaspoons of this topping into the bottom of each cupcake well (start with one teaspoons to make sure you have enough for all the wells). Place four pineapple tidbits on top and then a cherry half in the middle.

Measure and then mix together dry ingredients in a bowl and set aside.

In a stand mixer, cream together the butter and the sugar until fluffy. Add the egg and vanilla and mix thoroughly. Add the flour alternately with the pineapple juice. Don’t over mix, spoon about 1/4 cup of batter over each pineapple slice and bake for 20 minutes. Cool 20 minutes in pan then invert over a baking rack. (Because my cupcake tin is a 24-cup I inverted on my counter with foil and wax paper lining).

If you want to get extra fancy you could whip up some fresh whipped cream and place a dollop on each one.

Enjoy.