An Upside Down Success!

Let's be frank, friends. January was a disaster. And honestly I needed a month to recuperate. Alright, maybe it was more than a month. Maybe it was a couple plus a few days...but who's counting right? Right??

So, my baking confidence shattered, my will to create in utter disarray, and my sweet tooth feeling too ashamed to go on, I approached this month's cake for The Cake Slice Bakers with a bit of apprehension. Pineapple Upside Down Cake... I couldn't handle velvet, so how was I gonna handle something that wasn't even right side up?!

Help. Help was needed. And it came in the form of my wonderful baby sister, home from college for spring break and feeling a little kitchen deprived in any case. And then pile onto that help some advice from mom and grandma, and we were in business. (Did I mention it felt like my ENTIRE FAMILY was always around this week? A little different than time with just me and the Newf.) Grandma and Mom lent their "southern wisdom" (they did live in Savannah once, after all) and helped me scout out the ancient cast iron skillet, which has done nothing but take up space in our under-stove drawer and make it impossible to move due to the 40 pounds of cast iron heft therein.

Anyway. I tackled the topping, which involves layering butter, brown sugar and pineapple into the skillet.

You then dump the incredibly thick cake batter lovingly prepared by your sister over the top...

Mush it around a bit...

Put it in the oven, throw your hands up to the high heavens, and hope it comes out looking something like this!

Comprehend the miracle that has happened, take a deep breath, and savor the moment. (And maybe poke your cake a little to make sure it's done.)

Then comes the tricky part... loosening the darn thing from the 50 pound skillet. I pounded and rapped on the back side and eventually it fell out, and glory be this is what it looked like!

And yeah, that is me in the background, scraping out the rest of the brown sugar topping with my fingers. And mushing a little onto the holes in the cake (my hands were clean). And then of course eating the rest of the gooey brown sugar left in the pan. What a heathen I am. I won't post the picture of me caught in the act, but I'm sure you can imagine.

Anyway, I nervously awaited taste testing until the next day, when I hauled the cake to a girls' lunch with the family and some friends. We got to put it on their lovely china and lovely linens.

All in all, I'll agree with some of our other cake slicers... This was a very dense cake. But it was plenty moist, rather lovely to look at, and tasted pretty darn good. I had seconds. Maybe thirds later. Maybe I lost count after that... Maybe don't tell on me? With two people, this cake came together really quickly, and without much fuss or clean up even. Definitely one I would make again, should the need arise. And if you're not sold on what I have to say, visit the other cake slice bakers for a second opinion.

[Photographs for this entry were graciously provided by my sissy and her nikon. She saved my butt x2 apparently... Talk about personal creativity being at a low! Thanks sistah!]

Pineapple Upside Down Cake from Southern Cakes (by Nancie McDermott)

Pineapple Topping:

  • One 20-ounce can pineapple rings (save the juice)
  • 4 Tbsp butter
  • 2/3 cup firmly packed brown sugar
  • 10 maraschino cherries


  • 1 1/2 cups all purpose flour
  • 3/4 cup sugar
  • 1 1/2 tsp baking powder
  • 1/2 salt
  • 1/2 cup milk
  • 4 Tbsp butter, softened
  • 1 egg
  • 1 tsp vanilla extract
  • 2 Tbsp. pineapple juice

Heat the oven to 350F.

Drain the pineapple well but save 2 tablespoons of the juice for the cake batter. Melt the butter in a 10 inch cast iron skillet over medium heat. Or, put the butter in a 9 inch round cake pan and put it in the oven for a few minutes as the heat melts the butter.

Remove the pan from the oven or stove and sprinkle the brown sugar over the buttery surface. Place the pineapple rings carefully on top of the scattered brown sugar and melted butter, arranging them so they fit in 1 layer. (You may have a few left over). Place a cherry in the center of each ring, and set the pan aside.

In a large mixing bowl, combine the flour, sugar, baking powder and salt. Use a fork to mix them together well. Add the milk and butter and beat well with a mixer, scraping down the bowl once or twice until you have a thick, fairly smooth batter, about 1 to 2 minutes.

Add the egg, reserved pineapple juice and the vanilla. Beat for 2 minutes more, stopping once or twice to scrape down the sides.

Carefully pour the batter over the pineapple arranged in the skillet or cake pan and use a spoon to spread it evenly to the edges of the pan. Bake for 35 to 40 minutes until the cake is golden brown and springs back when touched lightly in the center. Cool in the skillet or pan for 5 minutes on a wire rack.

With oven mitts, carefully turn out the warm cake onto a serving plate by placing the plate upside down over the cake in the pan and then flipping them over together to release the cake onto the plate. Serve warm or at room temperature.


  1. I scraped the cake pan for the brown sugary bits too. Lovely little bits of sugar and butter they were too. Your cake looks wonderful.

  2. Wow fantastic job! it looks beautiful and very delicious:)