Pineapple Upside Down Cupcakes & Matching Cocktail

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.

Quickie Black Forest Cake & Cherry Bomb Cocktail

Another "Quickie" recipe using a cake mix and canned frosting.  This was a last second birthday cake for my dad, but I think it turned out great! Devil's Food Cake, white frosting, chocolate and Kirsch-soaked-cherry filling, shaved semi-sweet chocolate on top.

This recipe could easily be adapted for cupcakes, simply change the baking time according to directions, and put the filling in the center of the cupcakes after coring them.

Cherries are currently out of season, but I found amazing jarred and pitted Bing cherries that were perfect for garnishing.  For the filling, I used more traditional and cheaper canned cherries.

Make sure you use cake pans for this recipe, as we are going to be layering, and straight sides will make your life much easier!  Unfortunately my cake pans taper out slightly, which created uneven sides, but frosting covers this up pretty well. ;]

Next time I will do more cherries on top to accommodate smaller slices.

There were some leftover ingredients that resulted in a yummy cocktail I have dubbed the "Cherry Bomb."  Recipe will follow the cake recipe.

Quickie Black Forest Cake

• 1 box Devil's Food Cake Mix, plus ingredients needed for mix (24 cupcakes size, normally you need eggs and vegetable oil)
• 2 cups of strong coffee at room temperature, separated (you may not need it all)
• 2 cans white frosting 
• 1 can chocolate frosting (for the filling)
• 2, 14 ounce cans of pitted cherries (Bing cherries recommended)
• 1 ounce grated semi-sweet baking chocolate
• 1 200 ML bottle of Kirschwasser (clear cherry flavored brandy)
• 8-16 pitted Bing cherries with stems (optional, for decorating, can use canned if out of season)

~Drain the 2 cans of cherries, saving the juice from at least one of them in a separate container.  Place the drained cherries in a bowl, and soak in Kirschwasser. Use the whole bottle, or just until the cherries are covered.  Let them soak until you are prepared to start assembling your cake.


~Follow the directions on the cake mix for preheating and mixing instructions, substituting the coffee for the amount of water the recipe calls for.  (I checked 3 minutes before the earliest recommended baking time)

~You should have some coffee left over, as the mix I used only used 1 1/3 cups of coffee.  Mix 1 tablespoon of your extra coffee into your chocolate frosting.  If this makes the frosting too liquidy for you, pop it in the fridge while the cupcakes are baking and cooling, and it should firm up.  (Worse comes to worst, add in powdered sugar a teaspoon at a time until it reaches the consistency that you want)

~After the cakes have fully cooled, slice them in half horizontally.  You should now have a total of 4 layers.  You are now ready to assemble!  

~Drain your cherries that have been soaking in Kirschwasser, adding the runoff liquid to the cherry juice you had saved earlier.  This is what you will be brushing on top of the cake layers.  (You will have extra Kirschwasser/cherry juice leftover, which will come in handy for cocktails later! ;])

~Place a layer of cake on a serving plate, cut side up.  Brush lightly with the Kirschwasser/cherry juice mixture.  Spread a thin layer of your prepared chocolate frosting, and spread roughly 1/3 of your Kirschwasser soaked cherries as evenly as possible.  It is ok if your frosting crumbs up while spreading.

~Place another layer of cake on top, cut side up, and repeat the previous step.  Repeat the process with the third layer as well.  Place the fourth layer of cake on top of the last prepared cake layer, cut side down.  This will provide you with a smooth top surface for decorating.

~Frost the sides and top of your cake with your cans of white frosting, saving at least half of a can for the piping on top.  If possible, save an entire can for the piping.  Take your time, trying not to pull up any crumbs.  This really only matters on the sides, as the top will be covered in the next step.

~With the white frosting you have left over, pipe roses of frosting around the edges of the cake.  I used a 1M tip, starting in the center of where I wanted to pipe, working outwards.  Starting on the outside will give you a more traditional swirl of piping. (I originally piped 8 roses, but I will try to increase this number next time so the slices aren't so large! haha)

~Using a spoon, take your grated chocolate and sprinkle it in the center of your cake, and around the roses you just piped.  Top each rose with a Bing cherry, and you're now ready to enjoy!

Cherry Bomb Cocktail

• 2 shots of the Kirschwasser/cherry juice mixture leftover from recipe above (can substitute Kirschwasser and grenadine)
• 1 shot of whipped cream vodka (Pinnacle!)
• 1 cup of cherry flavor soda 
• Bing cherries for garnish

~Pour first two ingredients into a tall glass with ice.  Top with cherry soda.  Stir, and garnish with a cherry.  Cheers!

Cupcakes & Cocktails Party

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