When life gives you an industrial sized can of pineapple chunks, make pineapple upside down cupcakes!

Really, it was my own fault. For my 1960’s themed birthday party, I decided to make-you guessed it-1960’s themed appetizers. In addition to a number of delightful hors d’ oeuvres like ham wrapped dill pickles and cheese olive skewers (really, did people in the 60’s have no tastebuds???), I also made little smokie-pineapple-maraschino cherry skewers. Yeah. Those were a hit, let me tell you. I guess I thought I was making enough appetizers for a small army because I purchased the commercial sized can of pineapple chunks from Costco. Who buys those things? Even after making 50 or so of my oh so delicious (no, just weird) and incredibly popular (not so much) skewers, I had 2/3 of this huge can left.

What do you do with that much pineapple?


Duh! You make pineapple upside down cupcakes, of course!

Since I couldn’t find a recipe that really fit my vision, it would have been much easier to just make a pineapple upside down cake. But, we were headed to a supper club party and the idea of individual cupcakes seemed to fit much better. So, I winged it.

Combining a few different recipes, here’s what I came up with.

Pineapple Upside Down Cupcakes

I used 3 different recipes from Southern Cakes and got the idea for how to make the caramelized bottom(top) from Delish
For the caramelized bottom:
12 Tablespoons dark brown sugar
12 Tablespoons butter
24 pineapple chunks (reserve pineapple syrup for the cake batter)
12 maraschino cherries
Preparation:
Preheat oven to 350. Line a cupcake pan. Place 1 T of brown sugar and 1 T of butter in each cupcake liner. Cook until mixture has caramelized, about 10 minutes. Place 2 pineapple chunks and 1 cherry in each liner. Set aside.
For cake:
1 1/2 cups flour
3/4 cups sugar
1 1/2 t baking powder
1/2 t salt
1/2 cup milk
4 T butter, softened
1 egg
1 t vanilla extract
2 T pineapple syrup
Preparation:
In a large mixing bowl, combine the flour, sugar, baking powder and salt. Use a fork to mix them together well. Add the milk and butter and beat well with a mixer at medium speed, scraping down the side of the bowl once or twice until you have a thick, fairly smooth batter (1-2 minutes). Add the egg, pineapple syrup and the vanilla. Beat for 2 minutes, scraping down the bowl once or twice.
Carefully pour the batter in the cupcake liners, filling each normal-sized liner 2/3 full. Bake at 350 for 35-40 minutes, until the cupcakes are golden brown. Remove and cool.

For Filling:
20 ounces crushed pineapple, do not drain (I blended 20 ounces pineapple chunks in syrup)
2/3 cup sugar
3 T butter
3 T flour
salt
Preparation:
In a medium saucepan, combine the pineapple, sugar, butter, flour and salt and bring to a gentle boil over medium-high heat. Reduce the heat to maintain a gentle simmer and cook for about 5 minutes, stirring often, until the butter melts and everything comes together into a chunky sauce. Remove from heat and allow to cool.
Meanwhile, cut out the center of your cupcakes. Using a small paring knife, cut holes in the center of your cupcakes–roughly 1/2 inch in diameter and 1 inch deep. Do not cut all the way to the caramelized bottom.
When filling is cool, fill cupcakes using the largest cap on your piping bag.
For Frosting:
1 cup milk
2 T flour
1 cup butter, softened
1 cup sugar
1 t vanilla
12 maraschino cherries
Preparation:
Combine the milk and flour in a small or medium saucepan. Cook over medium heat for 3-5 minutes, stirring often and well with a large spoon until the mixture becomes thick, shiny and white, like very softly whipped cream. Set aside to cool. To complete the frosting, beat the butter with a mixer at high speed until light and fluffy. Add the sugar in 3 batches, beating well each time. Add the vanilla and then the thick, cooled milk mixture. Beat for about 2 minutes more, stopping often to scrape down the bowl until the icing is fluffy and soft and thick enough to spread.
Spread frosting on cupcakes and top each with a cherry.

These were a huge hit!
You could make them without the frosting and filling and just tip them over to be true upside down cupcakes. That seemed a little boring to me, so I added all of the other business…
There’s so much going on here, but it all works to make an insanely delicious pineapple concoction.