Pineapple Upside-Down Cake

Five months ago, during a bout of insomnia, I speculated here whether or not it was possible to take an attractive photograph of a pineapple upside-down cake.  This, of course, prompted me to make that very cake in order to photograph it.  Which I did a week later.

While the picture was okay, I wasn’t satisfied with the recipe.  Despite its homemade batter, Ree Drummond’s recipe still tasted like all other pineapple upside-down cakes…kind of fake.  No offense meant to Drummond.  Then it hit me that the problem was partly the use of canned pineapple and maraschino cherries.

I am not one to picket the canned food aisle.  One of my favorite vegetables is canned lima beans.  And I certainly am not going to tell you how bad for you maraschino cherries are.  I love them and have been known to add them to my diet Sierra Mist, thereby making it deliciously bad for me and less…ahem…diety.  Therefore, the change from canned pineapple and jarred cherries was purely for taste rather than for taste plus a holier-than-thou, look how healthy I can be reasons.  Face it.  This cake is not healthy and can’t claim to be, and that’s okay with me.

Oh, and if you have a cherry aversion?  Don’t.  My husband, who hates cherries, enjoyed this cake.  The cherries melt and take on the flavor of pineapple.  Pineapple flavored cherries = pure deliciousness.

Pineapple Upside-Down Cake

inspired by Ree Drummond’s “Pineapple Upside Down Cake” recipe in her first book, The Pioneer Woman Cooks: Recipes From An Accidental Country Girl, (William Morrow, 2009), pages 228-229

*Note: I made several changes to Drummond’s recipe.  I not only traded fresh fruit for the canned and jarred kinds, I also played with the amount of milk called for by supplementing some of it with buttermilk.  Finally, I replaced the shortening she called for with butter.  Oh, yeah, and I omitted the extra pineapple juice.


Topping (or Bottoming)-

1 medium pineapple

1-1/2 cups sweet cherries

4 Tbsp unsalted butter

1-1/4 cups light brown sugar


2 1/2 cups all-purpose flour

3 teaspoons baking powder

1 teaspoon salt

8 Tbsp (1 stick) unsalted butter, room temperature

2 cups granulated sugar

2 extra-large eggs, room temperature

2 tsp vanilla extract

1 cup milk, room temperature

1/2 cup buttermilk, room temperature


Not usually one for mis en place– setting out everything I’m going to us beforehand– I went that route this time.  It does make life easier.  Thought you’d like to see which brands I used.  I don’t know exactly how much of a  difference some of them make, but I’d wager the King Arthur Flour makes a bit of one (they don’t know who I am, I just like their flour).

First this is first, you want to make the topping.  Or would that be bottoming?  It is an upside-down cake.  Hmmm.  Best not to ponder these things.


Twist the top off of the pineapple.  Did you know you can do that?  You grab the pineapple in your non-dominate hand, football style.  Then you grab the top with your dominate hand and twist.  The top comes off perfectly.  Sure, you could also lop the top off with a knife, but where’s the fun in that?

Then cut the rind off.  Remove the knobby eyes now if you want, or wait to cut them off.  I waited because I’m a procrastinator.

Cut the pineapple around the core.

Then chop it up.  I chopped mine on a tray to catch the pineapple juice.  I thought I might use it in the cake batter like Drummond does, but I ended up changing my mind.

Put the pineapple into a colander over a bowl to drain any remaining juice.  Now, I should have done this as soon as I finished chopping my pineapple; however, as the photos below illustrate, I didn’t.  That said, I chose to rearrange the photos just for you, because you want to learn from my mistakes, right? I’ll pretend you said right.

Now for the cherries.  Remove their stems.  Then wonder where your cherry pitter went when you moved a little more than two-and-a-half years ago.  Then wonder to where the huge cube-o-paper-clips ran away.  Grumble and remember a tip you once saw about using a pastry tip to pit cherries.  See, there it is, all beautiful and perfect on the lower right portion of the picture below.

Grasp a cherry in your non-dominant hand.  Using your other hand, bring the pastry tip towards the part of the cherry where the stem once resided. (Thanks to my hubby for taking these cherry pitting process shots for me.)

Stick it in the cherry.

Twist and pop.  It’s like a horror movie, huh?

Pull the pit out, and repeat the process.

Mourn the demise of your once beautifully, perfect pastry tip with a blurry photo.  Sniff. (Oh, and took this photo, so I’m to blame for the blurry.  It’s time for new glasses.)

Now you have a bowl of perfectly pitted cherries in the midst of what looks like a crime scene.

Roughly chop up the cherries.  Put everything to the side while you mix up the cake batter.

For the cake batter, have your sous chef stir together the flour, baking powder, and salt in a large bowl.

In the bowl of a stand mixer (or you can do it with a hand mixer or even just a wooden spoon– your call), cream (mix together until it’s light and fluffy) together the butter and granulated sugar.

Add the eggs one at a time, then the vanilla, which I didn’t show you.

Alternate adding the flour mixture and

the milk and buttermilk.  Start and end with the flour.

The batter is very thick and light and fluffy.

See?  Yummy.

Heat a 10-inch cast iron skillet on medium-low heat.  When the whole pan is evenly heated, add half (4 tablespoons) of a stick of butter to the pan.  Let it completely melt evenly.

No cast iron pan?  I don’t know what to tell you.  I guess you could make it in a regular cake pan or a baking dish, but I haven’t tried it that way, so I wouldn’t be able to give you the slightest clue as to what changes to make.

Oh, and now is when you want to pre-heat your oven to 350 degrees.

Once the butter is melted, sprinkle the brown sugar (and it is a lot of brown sugar) evenly over the melted butter.  Blurry photo!  See how the bottom part is all melted looking?  You want it all to look that way.  Don’t burn the brown sugar!  It won’t taste very good if you do.

Then sprinkle the pineapple and cherries even over the melted brown sugar.  You can get fancy if you want to, but I don’t think any cake made in an iron skillet is meant to be fancy.

Pour the batter over the fruit.  Another blurry picture!

It’s a lot of batter, and that pan is hot and heavy.

Bake your cake in the pre-heated oven.  Drummond’s recipe says 30-40 minutes.  Mine took an hour.

Test for doneness by inserting a wooden skewer.  Goo stuck to the skewer?  Not done.  Clean skewer?  Done.

The funny top (bottom) is because I laid a piece of aluminum foil over the top to keep it from over-browning, and the foil stuck.  If you do that, spray the foil with non-stick spray first.  Okay?  Okay.

Allow the cake to cool for twenty minutes or so.  See the clock in the background?  I started working on this cake around 1:30 pm.  It takes some time.

Run a knife around the edge of the pan, then place a serving plate over the top,

and invert the whole thing.

Be careful, there’s hot, melted sugar in there.  My husband helped because (1) that pan + that cake = heavy and (2) I have an aversion to hot, melted sugar.  Want to see the scar?  It’s still there after almost eight years.

Here it is.  Caramelly, melty, fruity, gooey goodness.  It isn’t perfect or beautiful, but it smells divine and tastes even better.

We ate half of it that night and I had to make do with the other half for shooting purposes.

So, is it possible to make Pineapple Upside-Down Cake beautiful?  Not for me, but it sure did taste amazing.  The cake was soft and moist.

The topping melts in the mouth.  Fresh fruit made a tremendous difference.  The cake itself didn’t have that bubblegum flavor that I’ve come to associate with boxed mixes and canned fruit, and that was a good thing.  The buttermilk/ milk combination also made the cake much less dense and  gooey.

Final verdict: Rustic, delicious, and perfect in its imperfections.  This cake is completely worthy of a special occasion.

Yield: 1 10-inch cake, 12-18 slices, maybe more

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