alcohol, baking, booze, cakes, Featured

Happy National Pineapple Upside Down Cake Day

April 20, 2017

Now With Booze!

Here’s how to make yourself feel less guilty for eating cake … and then make it more naughty. This is my take on the Pineapple Upside Down Cake.

Save a slice for yourself and send the rest to your friends and co-workers. They will appreciate the slight alcohol buzz with the sugar rush. If you do bring it to work, serve a piece to your manager before you ask for a raise. It cannot hurt your chances.

Its also 420 Day, but that’s not entirely legal in Pennsylvania yet. So if you cannot legally indulge in one vice here’s another (which is ironic): Alcohol

Sugar and an alcohol high at the same time.

In my version, I use real cherries and fresh pineapple. I know that most pineapple upside down cake recipes call for maraschino cherries, but those things are gross. Don’t believe me? Watch this: What is a Maraschino Cherry?

How dare you mess with nature’s goodness, sir!

But …

If you are going to mess with nature one should incorporate copious amounts of alcohol.

For this recipe, I currently have a stash of pitted black cherries (AKA My Drunk Slut Cherries) that were soaked in rum for more than a year. This will make a mighty fine maraschino cherry replacement.

I consider myself “chaotic good”.

Boozy Pineapple Upside Down Cake

What You Need:

  • Black cherries pitted and soaked in rum (In my opinion as long as possible. Three days minimum. I have mine for more than 6 months. The long soak doesn’t cook off in the oven.)
  • A fresh pineapple (Smell the bottom of the pineapple. If it smells fragrant then you are good.)
  • The Perfect Vanilla Cake recipe (see below)
  • Melted Butter & Brown Sugar Topping
  • 1/4 cup of rum with a pastry brush
  • 9x4″ cake pan

Note: If you don’t have a cake pan that high, use parchment paper around the rim to keep the batter from spilling over during baking.

Pan spray the hell out of the cake pan.
Peel, core, and slice the pineapple as thin as possible. Put to the side for now.

Melted Butter & Brown Sugar Topping

What You Need:

  • 1/2 cup (one stick) unsalted butter
  • 1 cup of densely packed brown sugar


  1. Melt the butter.
  2. Add the brown sugar and mix.
  3. Make sure you break down any clumped brown sugar.
  4. Pour the sugar into the cake tin.
  5. Neatly spread the pineapples and position the cherries into any available spaces.

Start on the cake.

The Perfect Vanilla Cake

  • 2 2/3 cups cake flour
  • 2 1/4 teaspoons baking powder
  • 1 teaspoon salt
  • 1 cup [2 sticks] unsalted butter, softened
  • 2 cups sugar
  • 4 large eggs
  • 1 cup whole milk
  • 1 teaspoon pure vanilla extract (the good stuff)


  1. Combine the flour, baking powder and salt in a separate bowl and put to the side.
  2. Mix the butter until it’s smooth.
  3. Add sugar and mix until fluffy.
  4. Add the teaspoon of vanilla to the eggs.
  5. Add the eggs one at a time to the butter sugar mixture. Make sure the egg is blended before adding the next.
  6. Alternate adding the flour to the mixture in two parts. Meaning: Add part of the flour mixture … blend / add part of the milk … blend / add rest of the  flour mixture … blend / add last of the milk … blend

Do not over mix! You’ll end up with an edible sponge.

Bake for 350°F for 70 minutes (yes, it’s a moist and dense cake) or until the cake tester comes out clean.

After resting for 15 minutes, run a sharp knife around the tin edge to loosen it and flip it onto a clean plate. Be careful the sugar is hot!

While the cake is still warm brush the pineapple tops with rum.

Share with people you like.

Brandy soaked cherries aka Drunk Slut Cherries with the chocolate

Story and photos by The Pastry Prophet

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