Pineapple Upside Down Cake


I had so much fun with the Game of Thrones-themed recipes that I decided to try something retro-inspired in honor of Mad Men. Pineapple Upside Down Cake seemed a perfect tribute, especially since the new season began in Hawaii. Plus I’d had my eye on Thomas Keller’s recipe for the cake in his book Ad Hoc At Home. I’m afraid I fell victim to beautiful food photography. In the book the pineapple upside down cake rests on a cake stand in a shaft of sunlight, semi-translucent like a jewel. It’s practically lit from within. One would expect no less from Thomas Keller.



Thomas Keller is such a trusted name in the food world, I felt confident that the cake would turn out perfectly. What could go wrong? There was one catch. TK bakes his PUDC in a silicone cake pan. I do not own a silicone cake pan and didn’t see why I should have to go out and buy one just for this recipe.

Three attempts and one week later, I decided to give it up and try another recipe. It’s not that they all turned out bad. (Though one was unsalvageable.) It’s that the cake browned on the outside before the inside was set, something I didn’t realize until the cake was already turned out on a plate. Yes, I tested it with my cake tester. But even when it came out clean, there was a little bit of runny batter at the center. So of course I gingerly fit the pan back over the cake, re-flipped it, and put it back in the oven. A little foil over the pan kept it from burning. But after all that rigamarole, the result just didn’t have as much caramelization as I wanted. As you can see in the photo, the pineapple is still bright sunny yellow.

Perhaps it’s all because I didn’t use the cotton-pickin’ silicone pan. But it seems to me that people have been making PUDC for decades in all types of pans. I tried raising the oven temperature but that gave me a burned bottom and a soggy interior. A friend suggested a cast iron pan: it worked but the cake was dry.

Then I found a recipe which used a cast-iron pan but a totally different method of caramelizing the pineapple. You see, Thomas Keller’s recipe makes a “schmear” of brown sugar and butter (and rum and vanilla) and spreading it on the bottom of the pan. Then you press the pineapple slices in, spread the cake batter over them, and bake it. The final recipe I tried was by Chef John at All Recipes.

Chef John’s recipe (and his helpful video) have you melt the butter and brown sugar (and rum and pineapple juice) in the cast iron skillet until they’re well combined. Then you lay the pineapple slices into what is pretty much a pineapple and rum scented caramel. His cake recipe uses brown butter, which is always a winner in my book. The brown butter cake batter goes over the pineapple slices, though the batter is not as smooth and easily spreadable as TK’s.


Notice how craggy and uneven the edges are on Chef John’s cake? The result definitely had the caramelization I was looking for, but I believe I cooked the butter and brown sugar too long because the edges of the cake turned out quite chewy. The flavor is rich and complex, but a softer texture would make the cake easier to slice and handle. If I bake this cake again, I will check it at 25 minutes because after baking to the recipe’s minimum suggestion of 30 minutes my cake was a bit dry. But as you know, ovens may vary.

Here’s Chef John’s recipe, with my notes added.

Pineapple Upside Down Cake

  • 1/4 cup butter
  • 3/4 cup light brown sugar
  • 1 tablespoon pineapple juice
  • 1 tablespoon dark rum (optional, but not really)
  • 1/2 small fresh pineapple, peeled, cored, and sliced
  • 1/2 cup butter
  • 1+1/2 cups all-purpose flour
  • 1/8 teaspoon ground cardamom (I left this out)
  • 1/2 teaspoon of vanilla paste or extract (my addition)
  • 1/2 teaspoon salt
  • 2 teaspoons baking powder
  • 1/2 cup white sugar
  • 1/2 cup cold milk


  • Melt 1/4 cup butter in a 12 inch cast iron skillet over medium-low heat. Stir in brown sugar, pineapple juice, and dark rum. Cook over medium-low heat until the sugar is dissolved and the mixture is bubbling, about five minutes. (Here’s where I went wrong. Really watch this and take it off the heat once it starts bubbling. I think the five minutes recommendation is a bit liberal; perhaps if you start the clock from when you put the butter in the pan. Mine cooked much faster.)
  • Remove from heat and spread the pineapple slices in a layer over the brown sugar mixture, completely covering the mixture. (He demonstrates this in the video: you’re creating a pineapple mosaic, not a shingled surface.) Set the skillet aside.
  • Preheat the oven to 400º.
  • Melt 1/2 cup butter in a small skillet or saucepan over low heat until the butter begins to brown and release a nutty fragrance, about five minutes. Watch carefully, butter burns easily. Remove from heat and let cool for 10 minutes.
  • Whisk together flour, cardamom (if using) salt, baking powder, and white sugar in a large bowl. Whisk in the egg and cold milk until just combined. Pour in the melted butter and stir to mix thoroughly.
  • Pour the batter over the pineapple slices in the skillet; spread evenly to cover. (I think “pour” and “batter” are misleading words here. It’s more like you dump a loose dough into the pan and gently spread it over the slices. Take care not to disturb the pineapple while you do this.)
  • Bake in the preheated oven until the cake begins to bubble around the edges, the top is browned, and a toothpick inserted into the center comes out clean, about 30-35 minutes. Let cool in the skillet for 10 minutes. (Again I suggest testing the cake at 25 minutes.)
  • Loosen the cake from the skillet by running a knife around the inside edge of the cake. Invert a large plate over the top of the skillet and flip over, releasing the cake to show the pineapple slices on top. (My cake was very sticky and took some prying to come loose. One thing that might help is to butter the sides of the skillet before you pour in the batter.)

Perhaps the most valuable thing I learned from this experience is that a slice of fresh, perfectly ripe pineapple is better than just about any slice of cake imaginable.


Will I still bake cakes? Oh, most definitely.

Thanks for reading!

Peggy Dancing GIF


Next Up
Sweet Pea Hummus
Game of Thrones Week Part III: Side Dishes

2 Replies so Far

  1. Hanner says:

    Found you through the game of thrones cast. Just wanted to agree that my experience in PUDC was very much like yours. I love the way it can look, I enjoyed the process of trying to find one that I loved, but the fruit itself was always better than the fruit with cake. (I also tend to eat the fruit out of pies and leave the goo and crust, though, so I am a heathen.)
    Nice to meet you(r blog)!

    1. Hello! Your comment came in a barrage of spam comments and I overlooked it! Sorry for the delayed response. I’m glad to hear someone agrees with me about PUDC. There’s nothing better than perfectly ripe pineapple.

Comments are closed.

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