Nothing says America/1950's like Pineapple Upside Down Cake and cocktails! Haha, I took it upon myself to turn the classic cake into a cupcake form. I didn't want to lose the cupcake shape by flipping them, but I wanted to keep the signature pineapple ring design, so I cheated and actually cooked the pineapples separately. You can do this while baking, so it doesn't add very much time. I couldn't decide on the design, so I did two variations using some cream cheese frosting.
The reason I decided to make Pineapple Upside Down Cake was due to the discovery that there was such a thing as a Pineapple Upside Down Cocktail! You only need two additional ingredients, so I highly recommend having a toast to your delicious cupcakes when you're done. ;]
This is a very simple batter. These cupcakes are all about what's on top!
Pineapple Upside Down Cupcakes
Makes 12 cupcakes
- 1 cup sugar
- 1/3 cup unsalted butter (room temp.)
- 1 egg
- 1 1/3 cups all-purpose flour
- 1 1/2 teaspoons baking powder
- 1/2 teaspoon salt
- 3/4 cup milk
For the Pineapple topping:
- 12 drained pineapple rings (Canned in juice, save the juice!! You'll need it for the cocktail)
- 1/3 cup unsalted butter
- 2/3 cup brown sugar
- 1 jar maraschino cherries (with stems)
- 1 can cream cheese frosting (I used so little I went with canned for once, but if you need a recipe, I like this one: cream cheese frosting )
~Preheat the oven to 350 °F. Prepare muffin tins with cupcake liners.
~In a large bowl, cream together 1/3 cup butter and sugar. Add in egg and beat until mixed.
~In another bowl, mix flour, baking powder and salt to blend.
~Gradually add your flour mixture to your butter mixture, alternating with the milk. You should start and end with the flour mixture. Mix just until incorporated.
~Fill cupcake liners three-fourths full and bake for 18-20 minutes, or until a toothpick inserted into the center comes out clean.
~While the cupcakes are baking, take a large saucepan and melt 1/3 cup butter with the brown sugar. Once sugar is dissolved, arrange pineapple rings in pan and heat on low for 5-7 minutes per side. Spoon the butter/brown sugar mixture over the rings as they cook. Once done, remove from pan and set aside to cool. Save pan syrup. (Be gentle when flipping, don't break your rings!)
~Once your cupcakes are done, cool in the pan for 5 minutes, then remove to a wire rack and cool completely.
~Take your cooled cupcakes and prick holes in the top of them. A toothpick or small knife will work. Take your syrup mixture you created from cooking your pineapples, and brush onto the top of your cupcakes. (If this mixture has cooled too much, it may have started to separate. If this has happened, just heat up slightly until clear again.)
~You are now ready to decorate your cupcakes! You can be traditional and go simply with a pineapple ring on top with a cherry in the middle, or you can twist this slightly and pipe a small amount of frosting in the center of the ring before adorning with your cherry. (This is what I did in the main image.) Another option is to pipe your frosting more like a traditional cupcake, and arrange a wedge of pineapple and a cherry as garnish.
~Either way, you are now ready to enjoy your delicious cupcakes! If all this baking has made you thirsty, read below. ;]
Pineapple Upside Down Cocktail
- grenadine (you'll need a splash for each drink you are preparing)
- maraschino cherries (from above)
- 1 part Cake flavored vodka (Pinnacle!)
- 2 parts pineapple juice (from above)
- (Martini glasses and shaker fun but not required!)
~Arrange a maraschino cherry in the bottom of each glass.
~Mix the pineapple juice with your vodka in an ice filled shaker, and pour into your prepared glasses.. Leave room for a little more liquid to be added.
~Slowly pour a splash of grenadine against the side of your glass, until the desired amount pools to the bottom. (Worried about messing up the layers? Take a note from Black and Tan cocktails and pour onto a large spoon that is touching the side of the glass. Don't count yourself beaten too early either, waiting 5 minutes may be all you need for any stray grenadine to sink to the bottom.)
~Cheers! Nothing goes together like cupcakes and cocktails.
