Pineapple upside down cake

Bottom’s Up Cake (Bourbon-infused Pineapple Upside-down Cake)

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Turn your Cake ‘Bottom’s Up’!

Not your bottom PLEASE!  Just say  ‘Bottom’s Up’ and ‘Cheers’ to this Bourbon-infused Pineapple Upside-down cake- This new twist on a retro favorite is deliciously moist and luscious with caramelized pineapple and cranberries.  The Buttery juices and Bourbon literally seep into the cake for a deeper flavor profile- easy enough for every day- but gorgeous for the Holidays!

Just one bite of this spiked pineapple upside-down cake and you will be sold!   This isn’t your Grandma’s Upside down cake!  We have amped up this classic cake and we guarantee your gang will ask for more. You’re going to love this cake.


The more you weigh, the harder you are to kidnap. Stay safe. Eat dessert.


Why will I love this Bourbon Pineapple Upside down Cake recipe?

  1. This is a delicious cake AND everyone needs a little tropical decadence in their lives
  2. This cake is Gorgeous- perfect for a special occasion, and so pretty for the Holidays
  3. It’s easy!  Everyone loves to make the cake that is fast and simple
  4. The Bourbon, butter and brown sugar gives this moist and spiked cake something special – a deep and interesting flavor profile



Cake topping

  • Butter
  • Brown Sugar
  • Bourbon
  • Crushed Pineapple
  • Dried Cranberries or Craisins


  • Duncan Hines Yellow Cake mix
  • Vanilla Pudding mix
  • Bourbon
  • Eggs
  • Olive Oil



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Heavy kitchen towel that says "If Swearing Burned Calories, I'd Be One Skinny Bitch"




What is with ‘Bottom’s Up’, ‘Cheers’ and all the

Clinking before Drinking?

Have you ever wondered why we do it?   

There’s more to it than you might think…

The tradition of raising and clinking glasses while wishing health and happiness  is so ancient and widespread, it’s almost impossible to know where it began.  Some think toasting might have started in Ancient Greece, honoring the Gods while drinking during ceremonies or feasts. Wine was poured out onto the ground in exchange for good health or an answered prayer. In present-day Greece, and in so many other places, it’s now traditional to raise your glass upwards to the heavens as though offering a sip to the gods.

The Romans built upon the Greek custom of drinking to others’ health and well-being.  They added toasted bread crumbs to their goblets, reducing the acidity of the often bitter wine.  Hence, giving us the tradition of ‘Toasting’.

In another theory, Medieval clans would fill their glasses to the brim and clink hard enough that a bit of liquid from each glass would splash into the other. The rough clinking would spread the poison, and therefore ensure that any poison would lead to mutual destruction.

In addition, it’s been said that vessels were clinked together, accompanied by shouts and cheers, to ward off evil spirits.  This tradition still survives in German culture today, when mugs are banged on the table followed by shouting to scare off ghosts.


Be Careful how you Toast

  • An old legend suggests, not looking into someone’s eye when you toast, might get you 7 years of bad sex
  • Clinking glasses with water is unlucky across many cultures. It’s believed that the act brings bad luck or even death upon the recipient
  • The U.S. military actually forbids toasting with water. Naval folklore claims that a toast with water will lead to death by drowning

While “cheers” is the most frequent toast in the English-speaking countries, “to your health” or simply “health” is the customary toast in many other European languages: such as Santé in French, Salute in Italian, Salud in Spanish, and Saúde in Portuguese.

Toasting Traditions from around the World



Bottoms Up!  to an amazing new Bourbon-Infused Pineapple Upside down Cake

Pineapple upside down cake
5 from 116 votes

Pineapple Cake

Bourbon Infused Pineapple Upside-down Cake
Prep Time15 minutes
Active Time35 minutes
Total Time50 minutes
Course: Dessert
Cuisine: American
Keyword: 'cock'tail, Boozy cake with fruit, Boozy Pineapple cake, Boozy Pineapple upside down cake, Bourbon cake, Bourbon Pineapple Upside down cake recipe, Bourbon Pineapple Upside-down cake, Bourbon-infused cake, Cake with Bourbon, Drunken Pineapple upside down cake, Easy Bourbon and Pineapple cake, Easy Bourbon Pineapple and cranberry cake, Holiday Cake, Pineapple and cranberry cake, Pineapple Bourbon Cake, Pineapple cake with Bourbon, Pineapple upside down cake recipe, Pineapple Upside-down cake, Pineapple upsidedown cake, Spiked Pineapple upside down cake, Tipsy Pineapple upside down cake, Upside down cake, Upsidedown cake
Yield: 12



Cake Topping

  • 1 Stick Melted Butter
  • 1 Cup Brown Sugar
  • ¼ Cup Bourbon
  • 1 20 oz Crushed Pineapple (Drained/Pressed)
  • Cup Dried Cranberries


  • 1 Duncan Hines Yellow Cake Mix
  • 1 3.4 oz Vanilla Pudding mix
  • 1 Cup Bourbon
  • 4 Eggs
  • 5 oz Olive Oil


Get ready

  • Preheat oven to 350 degrees
  • Cover the inside of the Bundt pan with cooking spray

Combine Fruit mixture

  • Combine butter, brown sugar, bourbon, pineapple, and dried cranberries in a bowl and mix well
  • Add fruit mixture to the bottom of the prepared Bundt cake pan, and spread evenly- Set aside

Prepare the Cake batter

  • Add cake mix, pudding mix, bourbon, eggs, and oil to the mixing bowl and combine with the mixer until the batter is even and mostly smooth
  • Pour the cake batter into the Bundt pan, on top of the fruit mixture to form a second layer

Bake the Cake

  • Place the cake in the oven to bake
  • Bake for approximately 35 minutes
  • Insert a toothpick in the center of the cake to test that the cake is done (The toothpick should come out clean)
  • Remove the cake from the oven, and let it cool for 10 minutes

Turn upside-down and Serve

  • Rest your cake platter on top of the Bundt pan. Put a mitted hand underneath the Bundt pan, and your other hand firmly holding the platter on top. Slowly invert the covered pan- and then carefully lift off your Bundt Pan
  • Scoop the remaining fruit from the bottom of the Bundt pan and place them to fill in spots on the top of your cake
  • Serve and enjoy

Make Sure your Bourbon-infused Pineapple Upside-down Cake- So Easy

  • Step 1:  Grease your Bundt Cake, and Preheat your oven to 350 degrees
  • Step 2:  Mix your melted butter, brown sugar, drained pineapple, bourbon, and dried cranberries together- and then pour into your greased Bundt cake pan.
  • Step 3:  In a mixer, combine your Duncan Hines cake mix, Pudding packet, Bourbon Eggs and Olive oil
  • Step 4: Pour the cake batter on top of your fruit mixture
  • Step 5: Bake the cake for 35-40 minutes
  • Step 6:  Allow the cake to cool for 10 minutes. Put your cake platter upside down on top of the Bundt pan and then flip! (Gently)


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Where did the idea of a Pineapple Upside Down cake come from?

In the early 1920’s canned pineapple was readily available in the United States.  The Dole company ran a recipe contest using their canned pineapple- and over 2500 recipes were submitted.  A Pineapple Upside-Down cake recipe took 1st place and its popularity took off.  The idea come from early skillet cooking over a fire.  It was traditional to put fruit and sugar at the bottom of a pan and a simple cake batter on top.

Maybe symbolism also played a part of this cake’s popularity?  The word Pineapple actually means “Prosperity arrives”.  A great sentiment for your next celebration.


Never Blame someone else for the road you're on- That's your own Asphalt



Aphrodesi’hacks’ for a Bourbon-infused Pineapple Upside-down Cake

  • When you make this Bourbon pineapple upside-down cake, follow this recipe- and disregard the Duncan Hines box cake instructions
  • You can use crushed pineapple, chunk pineapple, pineapple slices, or pineapple rings. Just be sure to properly crush the pineapple, and press the juice out.
  • Do a good job of pressing the pineapple juice from your pineapple- too much moisture and the cake could fall apart
  • Cooling time is key for turning over a beautiful cake- Too little time and the cake is not set enough, too much time and the cake is harder to move.
  • THE FLIP:  Put your serving plate or platter directly on top of you Bundt pan.  Place your mitted hand underneath the Bundt pan, and your other hand holding the cake platter firmly in place.   Turn over gently- and then slowly remove the Bundt pan
  • There may be some remaining pineapple and cranberries in the pan – scoop them out a selectively place them back on the cake
  • Rum can be substituted, if you prefer a sweeter cake
  • I love to eat this while warm


When does old enough to know better set in?


FAQs for making a Bourbon-infused Pineapple Upside-down Cake


Why is it called pineapple upside down cake?

It is called a pineapple upside down cake because it is baked with the caramelized pineapple on the bottom of the pan and then inverted for serving.


Can I use fresh pineapple instead of canned?

Fresh pineapple will work instead of canned crushed pineapple.  Be sure the pineapple is properly crushed and the juice is pressed out before using.


Why is my upside down pineapple cake soggy?

Your pineapple may have been too juicy. If you’re using canned pineapple it has a lot more liquid than fresh. Make sure to press the pineapple well before adding it to the Bundt pan


Can I make this cake in advance?

You can, but I highly recommend making it fresh. It truly tastes best enjoyed warm, fresh from the oven.


Why would I want to have Bourbon add to my cake?

Bourbon is a complex flavor profile that can add distinctive character to baking.  Whether it is a Tipsy, Spiked, Boozy or Drunken cake recipe – Bourbon can add  a woody flavor profile that may include notes of oak, walnut, and almond.  Alternatively, a spicy Bourbon may feature notes of black pepper, clove, cinnamon, and coffee


Does the alcohol in a cake remain as potent after baking?

According to the U.S. Department of Agriculture (USDA), baked or simmered dishes that contain alcohol will retain 40% of the original amount after 15 minutes of cooking, 35% after 30 minutes and 25% after an hour.

Enjoy your Bourbon-infused Pineapple Upside-down Cake


Other great Cuss Kitchen® Cakes:

Slice of Cassata CakeCussata Cake Our Italian-inspired Cake with Strawberries and Ricotta is a simplified version of the classic Italian cake that gives you delicious Ricotta cheese, and fresh strawberry layers. While the traditional Cassata cake recipe was made for Easter, the CUSSata cake makes a delicious and light dessert for any Holiday.  Especially beautiful while strawberries are in season.  Mama Mia!



finished shutthef-upcake - cupcake with alcohol pipetteShutthef*ckupcakes  Cupcakes with pipettes of Kahlua are conversation stoppers.    The best alcohol-infused cupcakes may cause exclamations of STFU! The combination of Chocolate, Toasted Coconut and Kahlua flavors combine to make a memorable dessert.  Change up what you bring to parties.  Shutthef*ckupcakes will be the star of the dessert table, and your friends will eat this sweet and boozy treat and have another.


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17 Responses

  1. 5 stars
    Love the tropical flavors of this cake. Enjoyed reading the information about how to toast – learnt something new today!

  2. 5 stars
    This cake is moist and really interesting with the Bourbon- Surprisingly EASY – I will make it again soon.

  3. 5 stars
    The best pineapple upside-down cake. Robust Bourbon flavor. I will make for the Holidays because we enjoy it and the Gold and Cranberry remind me of Christmas.

  4. I don’t like to drink Bourbon- but it really makes dessert flavorful. This is a great new twist on a cake I have always loved

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