Pineapple Upside-Down Cornmeal Masa Cake

"Pineapple Upside-Down Cornmeal Masa Cake," from Make It Like a Man!

A while back, I made a masa cornbread, and thought it’d make an interesting pineapple upside-down cake. Well, it did. This Pineapple Upside-Down Cornmeal Masa Cake looks like a party, and is a truly unusual, tasty treat. The caramelized pineapple and spicy jalapenos engage in an entertaining sword fight along your tongue, while tightrope-walking a thin line between sweet and savory.

Ingredients for one 12-inch round cake:

1 large pineapple (about 3½ lbs)
2 oz. butter (½ stick), plus more, optionally
7 oz. granulated sugar (1 cup), divided
3¼ oz. dark-brown sugar (½ cup, packed)
7½ oz. masa harina (1½ cup)
4½ oz. yellow cornmeal (¾-cup)
1½ oz. cake flour + 2¼ oz. bread flour (¾ cup all-purpose flour)
3 tsp baking powder
¾ tsp baking soda
1½ tsp salt
1 lb. + 3⅛ oz. milk (2¼ cups)
8⅝ oz. plain Greek yogurt (1 cup + 2 Tbs)
3 large eggs (5¼ oz. – supplement with melted butter if necessary)
5 oz. pickled jalapeno, chopped (a generous ⅓ cup)
5 oz. roasted red peppers, diced (a generous ⅓ cup)

How to do it:
  1. Prep the pineapple: you may have a favorite method, but mine is to slice off the top and bottom, quarter what remains; and then from each quarter, remove the flesh and core. Slice thinly. Set aside.

"Pineapple Upside-Down Cornmeal Masa Cake," from Make It Like a Man!

  1. Make a caramel: there are two ways to do this, but they both begin with preheating a 12-inch cast-iron skillet over high heat. Meanwhile, cut the butter into cubes and set aside. Now, you do can a “dry” method, or a “wet” method. Here’s my dry method dialect: pour the 3½ oz. (½ cup) granulated sugar into the hot skillet, making an effort to distribute it somewhat evenly. Watch for the sugar to begin to melt. As you begin to see caramelization, lower the heat to medium and swirl the pan. The pan will be hot and heavy, but I nonetheless prefer to use two very, very heat-resistant gloves to lift it right off the stove and tilt-a-whirl it. You’re going to make a very dark amber. The very second that the last of the sugar has melted, off heat. Distribute the butter evenly and give it a few seconds to begin to melt. Then, over medium heat, mix the butter into the caramel. I find a wooden spatula the best tool for this. Once mixed, off heat, distribute the caramel evenly across the pan, and sprinkle it with brown sugar.
  2. Arrange the pineapple slices carefully; the pan and the caramel will be hot. Remember that the pieces of pineapple that touch the bottom of the pan will be the top of the cake, so make an effort to make a nice design. The same is true for the sides of the pan: this layer of pineapple will be visible, so make sure to line the edge of the pan nicely with the pineapple.
  3. In a large bowl, whisk remaining 3½ oz. sugar (½ cup) with the rest of the dry ingredients. In another large bowl, mix the wet ingredients. Add the dry to the wet, whisk just until well blended, and fold in the jalapeno and peppers. Scrape this into the pan atop the pineapple. Bake until a tester – poked into the cake in several places – comes out clean, at least 40 minutes.
  4. If you intend to serve this from the pan (right-side up), rub a tablespoon of butter over the top of the cake just after you’ve removed it from the oven, to give the cake a sheen. If you’re going to serve it on a platter (upside-down), run a knife around the edge of the cake a few times to loosen it from the pan, place an inverted platter over the pan, and turn the whole thing upside-down. You must do this while the pan is too hot to touch without gloves; otherwise, the pineapple will stick to the pan. Flipping a hot, tremendously heavy pan will not be easy! But it can be done.

"Pineapple Upside-Down Cornmeal Masa Cake," from Make It Like a Man!

Notes:
  1. The masa in this cake gives it a heft and the grittiness of the cornmeal give it and seriousness that keep it from being an out-and-out dessert, yet the caramel and pineapple seem to thumb their noses at anything but a dessert.
  2. I can kick myself for not taking a picture of the cake before inverting it. It looks quite festive right-side up. If you serve it that way, you can use a large serving spoon to extract portions the way you would a bread pudding.
  3. I prefer it warm or at room temperature, although it’s not bad leftover and refrigerated.
  4. The cake I modeled this one after had a custardy quality that this cake does not have. Why? I suspect because of the longer bake time and lower temperature, which I felt were necessary to effectively caramelize the pineapple and cook the increased amount of batter. However, although this cake’s texture is more like a traditional cornbread in some ways, the pineapple juices seep into it when you invert it, and that part becomes sticky-licking heavenly.

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Pineapple Upside-Down Cornmeal Masa Cake

Credit for images on this page: Make It Like a Man! This content was not solicited by anyone, nor was it written in exchange for anything. This cake’s sweet spiciness is exhilarating. I gave to Robert Dinero just before he walked on-stage at the Tonys last night, and, well…

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"Pineapple Upside-Down Cornmeal Masa Cake," from Make It Like a Man!

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25 thoughts on “Pineapple Upside-Down Cornmeal Masa Cake

  1. My Lynne has an addiction with jalapenos Jeff so the thought of caramelized pineapple and spicy jalapenos together already make this a cake recipe that would be welcomed in our house!

  2. Well ain’t that an absolute BEAUT!! I have never had cornbread or a pie made of pineapple so I have no idea what flavors to be thinking about right now HOWEVER I do know what they smell like and mannnnn do they smell GOOD!

    • Well, baked pineapple is incredibly good. It gets sweeter and softer, but still has this kind of … almost umami character.

  3. Jeff, I wish I’d read this sooner as I had a fresh pineapple cake disaster a couple of days ago. Instead of cake, it ended up with more of a spoon bread. Tasted good though.
    Your recipe sounds great, I’m going to give it a go using corn flower instead of masa harina. I love the idea of adding the peppers.
    Ron recently posted…The fresh potato and the Swedish obsession with them…

    • Good luck! I found that with masa, I had to check extra carefully for doneness. I don’t know if corn flour will create a similar situation. Also, I on the fence about whether it has enough sugar, too much, too little. I thought it was delicious, though. The peppers were Eva’s idea. They’re there more for color than flavor – but I think it’s an essential element. Without them, the pineapple blends in too much with the color of the cornmeal, and then the pops of green aren’t especially appetizing. Somehow, the red brings it all together and makes it look like a party. (The traditional cherry, though, I think would’ve been a poorer choice.)

    • Hmm, well, the pineapples break down in the oven, and the texture turns … I don’t have an easy way of describing it … soft, almost like a stiff gel, but with just a bit of the fibrousness still left in them. It’s incredibly satisfying. I would not think they could be grilled any more than sautéed apples could. But that is the direct affect of two things, I think: 1) their having been thinly sliced. If you slice them into thick steaks, their oven stint will not be long enough to break them down. I know that from experience. 2) I layered them such that they are a distinct layer, with batter resting on top of them. In the more traditional version, the pineapple rings kind of get nestled into the batter, which probably insulates them to some degree. (I’m guessing at that.) In any case, I think that if you cut them very thick, you might be able to grill them after the cake’s been baked.

  4. What a gorgeous pineapple upside down cake! I’d love to serve this to my dinner club after a Tex-Mex feast—so fun!

  5. Pineapple upside down is my new favorite you know 🙂 I love this cake. the pineapples are perfectly caramelized (or perfectly cooked and in roasted;) ) plus cornmeal is added which I never tried and a very well presented. yeah, this is a awesome recipe.

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