Classic Pineapple Upside Down Cake

It seems that lately I can't get enough of cookbooks. I guess I've always been that way, but even more so lately. The other day I was reading Thomas Keller's Ad Hoc and I came across this recipe for Pineapple Upside Down Cake. It just so happened that I had a fresh pineapple sitting on my counter, waiting to be a part of something special. And, if that wasn't reason enough, I had never attempted to make a classic Pineapple Upside Down Cake before.

As much as I take joy in creating a new recipe, every once in a while, I like to make a classic. No twists and turns, just something that has been made for years, in exactly the way it was intended to be made. While I carefully arranged the pineapple on top of the brown sugar mixture, I couldn't help but feel like I should be sporting a 50's inspired dress, frilly apron and those dark-rimmed glasses that point up at the ends and I liked that sort of connection to a dish. 

One of the things that surprised me the most about this dessert was just how easy it was to make and also, how much I liked the end result. (Although, that heavenly aroma that filled my apartment didn't hurt its case..). I guess this might be due to the fact that I made this dessert on a whim, once I realized that I had everything needed to make it. It wasn't sparked by a craving and it wasn't planned in advance. It just sort of happened. I didn't expect the cake to be so delicately soft and the fresh pineapple to mix so well with the brown sugar and butter mixture to form such a delightfully sweet topping. What's more is the topping makes (and keeps) the vanilla cake base so moist that the whole thing just sort of melts into one delicious bite.

If you haven't made a classic Pineapple Upside Down Cake before, I encourage you to pick a random and unassuming afternoon and give it a try. I've listed the recipe from Keller's book below and the only modification that I made was the fact that I added all of the brown sugar-butter "Pan Schmear", because, well, why not?

Pineapple Upside Down Cake
Recipe from Thomas Keller's Ad Hoc

  • Pan Schmear
  • 8 tablespoons (1 stick; 4 ounces) unsalted butter, at room temperature
  • 1 1/2 tablespoons honey
  • 1/2 teaspoon dark rum
  • 1 cup packed dark brown sugar
  • 1/4 teaspoon pure vanilla extract
  • Kosher salt
  • 1 Gold (extra sweet) pineapple

  • Cake
  • 1 1/2 cups cake flour
  • 2 teaspoons baking powder
  • 8 tablespoons (1 stick; 4 ounces) unsalted butter, at room temperature
  • 1/2 cup plus 2 tablespoons granulated sugar
  • 1/2 teaspoon pure vanilla extract
  • 2 large eggs
  • 1 tablespoon plus 1 teaspoon milk
1. Preheat the oven to 350 degrees. In the bowl of a stand mixer fitted with the paddle, combine the butter, honey, rum, brown sugar, and vanilla and beat until smooth and well blended. Spread 1/3 cup of the schmear over the bottom of a 9-inch silicone baking pan. Sprinkle lightly with salt. (The remaining schmear can be refrigerated for up to 2 weeks or frozen for up to 1 month; bring to room temperature before using.)
2. Cut the top and bottom from the pineapple and cut away the peel. Cut the pineapple lengthwise into quarters, and cut off the core from each section. Cut each piece into 1/8-inch-thick slices. Beginning at the perimeter of the pan, make an overlapping ring of pineapple slices with the curved side facing out. Make a second ring inside the first one, overlapping the slices in the opposite direction, working toward the center of the pan. Reserve any extra pineapple for another use.
Sift the flour and baking powder together; set aside. Put the butter and sugar in the bowl of a stand mixer fitted with the paddle and mix on low speed to combine, then beat on medium speed for about 3 minutes, until light and creamy, stopping to scrape down the sides as necessary. Mix in the vanilla. Add the eggs one at a time, beating until the first one is incorporated before adding the second and scraping down the sides as necessary. Beat in the milk. Add the flour mixture in 3 batches, beating until just combined. Pour the batter into the pan and spread over the pineapple. 
3. Bake for 15 minutes. Rotate the pan for even browning and bake for another 20 to 25 minutes, until a cake tester or wooden skewer inserted in the center of the cake comes out clean. Cool the cake in the pan on a cooling rack for 20 to 30 minutes.
4. Run a knife around the edges of the cake, invert onto a serving platter, and serve warm. (Leftover cake can be stored at room temperature for up to 2 days.)


Frederick Wright said...

Lovely! One of my favorite desserts of all time. Hard to imagine that dark rum is available in 1/2 teaspoon measures...

Leeanne said...

That is the most beautiful cookbook I own. I need to revisit it soon.

The Small Boston Kitchen said...

It's one of my favorites...I read it, cover to cover in one sitting!

Bianca @ Confessions of a Chocoholic said...

I've never attempted pineapple upside down cake either. This looks gorgeous!

Michelle Collins said...

Ooooh. I've never tried to make this myself, but I've always been a fan!

Mom said...

This looks and sounds terrific!! Any leftovers?!?!?!

Elina (Russian Bites) said...

I've never craved a pineapple upside down cake or felt the need to make it... until now. Saving it for future use. It does sound classic and fantastic. Thanks for sharing! :)

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