Food: Bourbon Pineapple Upside Down Cake Recipe

Finally, after a brief hiatus, I’m back at the bench and raring to go.  This past weekend our Canadian Thanksgiving gave me an opportunity to play around with some family favorites and I have one for you this week.  Desserts are always so accommodating to the addition of a little bourbon, adding another level of flavor and this cake is no exception!

Growing up, Mom made a rectangular Pineapple Upside Down Cake that resulted in a few headlocks during the years while 5 kids fought over 4 corners.  I found out recently that someone created a crazy cake pan that has more than four corners. Genius. All I can say is that when that brown sugar caramelizes into a crispy corner of deliciousness, accompanied by sweet juicy pineapple with that light golden cake, you should step aside because that piece is mine!  However, in an effort to keep the peace this Thanksgiving, I made a round pineapple upside down cake for our family gathering. The cake was met with comments like “what the heck” and “where the hell are the corners?” and “that cake is round”. It was delicious nonetheless.

The cake is made from scratch but if you want to use a boxed cake mix, as always, I won’t judge.  We all need to save a bit of time here and there but truthfully, it takes pretty much the same time to make this one and you get to say it’s made from scratch.  However, the boxed cake is acceptable in a pinch. After all, you are in the kitchen and you are about to bake with bourbon and we all know that everything is better with bourbon.  Note: if you are using a boxed cake, you will need to double the base ingredients and use 2 round pans OR use a 9x13 pan and watch the fighting commence…oh…those corners…


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Bourbon Pineapple Upside Down Cake:   

*this recipe makes 1 - 8” round cake


Butter – to grease pan plus 2 melted tablespoons

4 tbsp brown sugar

1 tin of pineapple, drained and reserving 3 tbsp juice (this is my time saver and I used crushed pineapple but you can also use “tidbits” or 6 slices (I used packed in its own juice)

10-12 cherries, glazed or maraschino – or as many as you wish

2tbsp + 1 tbsp  plus 2oz bourbon


3/4 cup of flour

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1 tsp baking powder

½ tsp baking soda

½ cup sugar

½ cup of butter, softened

2 eggs

2 tbsp bourbon

Plus the reserved pineapple juice


For the base:

  1. In a small bowl, pour the first measure of 2 tbsp of bourbon over the drained pineapple and set aside for 30 minutes or longer.  You will be draining the pineapple again.

  2. Pour the next measure of 1 tbsp of bourbon over the cherries and set aside with the pineapple.  These will be drained as well.

  3. Drain the pineapple and cherries.  Should you throw out the bourbon? Hell no.  Go ahead and add a few dashes of bitters and an ice cube, stir and you have yourself a makeshift old fashioned.  Tasty.

  4. Preheat the oven to 400F

  5. Grease the bottom and sides of your cake pan and pour the melted butter in the base.

  6. Sprinkle the brown sugar over the melted butter, be sure to cover the entire base.

  7. Gently spoon the drained pineapple overtop of the brown sugar.  Doesn’t it smell delicious? .

  8. Dot the pineapple with cherries and gently press into the pineapple.

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For the cake:

  1. Sift the dry ingredients in a large mixing bowl

  2. Add the eggs and butter and mix until just combined.  The mixture will be very thick.

  3. Add the reserved pineapple juice and the last 2 tbsp of bourbon.

  4. Mix until smooth and scrape out of the bowl and onto the pineapple.  The cake is not as thin as a box cake, so you will have to nudge it out of the bowl and into the pan. Use an offset spatula or knife to smooth the batter very gently over the pineapple.

  5. Bake for 30 minutes.

  6. While baking, pour yourself the 2 oz of bourbon to enjoy while the house fills with that familiar baking aroma.  You’ll also need to convince yourself that you can flip this cake without mishap. You know you can!

  7. Remove the cake from the oven and cool on a rack for 5 minutes then run a knife along the edge.  You need to flip this baby while it’s still hot. Place your serving plate over top of the cake pan – don’t forget the oven mitts!!  (been there, done that) and if one swift move, flip it over. You should hear the cake release. If you don’t, gently tap the bottom of the cake pan. I haven’t had one stick yet.  I have faith that yours will be perfect.

  8. Cool plate on a rack.  Serve with whip cream

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Have questions about the recipe or want to share your experience making this or show off your pictures of your cake?  Did your flip work? Did you make corners? Were there fights over them? I need to know! Leave a comment below or send direct message to me @canadian_proof .  I hope this easy, delicious cake becomes a regular addition to your baking line up.


Maureen Linehan


Jordan GrigsbyComment