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Fresh Pineapple Upside-Down Cake, from Martha Stewart Living

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Made with Fresh Pineapple

Tart cherries, instead of maraschinos, are folded into the cake, which is baked in a cast-iron skillet.

Yield: Makes one 10½-inch cake, serving 10-12 (possibly more). Source: Martha Stewart Living, July/August 1999

What You’ll Need:

2¾ oz. dried tart cherries [½ cup] ♦ 1 pineapple, (about 3½ pounds), outer skin removed and un-cored ♦ 4½ oz. cake flour [1 cup] ♦ 1½ tsp baking powder ♦ 7½ oz. granulated sugar [1¼ cups] ♦ 6 oz. unsalted butter, room temperature [12 Tbs, or 1½ sticks] ♦ 3¼ oz. packed dark-brown sugar [½-cup] ♦ 1 vanilla bean, split lengthwise, seeds scraped (substitute 1 generous tsp. of handmade, manmade, ideologically superior extract) ♦ ½-tsp pure almond extract ♦ 2 large eggs ♦ 9 oz. whole milk [6 Tbs] ♦ 8 oz. heavy cream, well-chilled [1 cup] ♦ 3 oz. dark rum [2 Tbs]

How To Do It:

Here are the directions, in a condensed form. See the full directions at Martha Stewart.

1. Soak cherries: 10 min; drain, chop. Slice pineapple. Sift flour, powder. 2. Preheat: 350°F. Caramelize 3 oz. sugar 12-inch cast-iron skillet over high heat, to deep amber, about 5 minutes. Off heat, add ½-stick butter. Spread caramel; sprinkle with brown sugar. 3. Arrange pineapple slices. 4. Cream butter, remaining 4½ oz. sugar. Add extracts. Add eggs. Add milk. Slowly add flour. Fold in cherries. Scrape batter into skillet. 5. Bake to golden brown (clean tester), about 40 minutes. 6. Pour off excess liquid. Carefully de-pan cake. Pour liquid on top. Whip cream w/rum to stiff peaks.

Notes:

1. You could probably get away with increasing the cake by 50%.
2. If you can get the cherries in bulk, great. If not, they’re commonly sold in 5-oz. bags. You might think, hey, that’s so close to the 4 oz. that I need … I’ll just use the whole bag. But you’d be wrong. A half-cup equals 4 oz. in a liquid measure; a half-cup of dried cherries weights about 2¾ oz. If you use the whole bag, you’ll nearly double the called-for amount, and your cake will go from pineapple upside down to pineapple over cherry.
3. Take the butter out of the fridge shortly before you start any of your prep work (before cutting into the pineapple, for instance).
4. I didn’t find it necessary to place a baking sheet under the skillet, but I can understand why one might.

4. If you’re one of those people who doesn’t believe in using soap on your cast iron, first you might want to re-think that, but secondly, you had better make damn sure that there’s no residue in the pan that’s going to impart a strange flavor to your cake.
5. With regard to the pineapple, of course you have a Japanese mandoline, don’t you? Use a sharp chef’s knife and simply slice as thin as you dare. I prefer a different pattern, so I quartered my pineapple lengthwise before slicing it.
6. Nuke the cherry water in a glass measuring cup water; I’m not sure what Martha has against the microwave.
7. You can do the sifting in your KitchenAid, and then transfer the flour mixture to a bowl when it comes time to cream the butter.
8. To caramelize the sugar, place it in the pan and swirl the pan to get the sugar into an even layer. If you wind up with some crystallization, don’t fret. Break it up as best you can while stirring in the butter. It will dissolve into the pineapple juice as the cake bakes.
9. To create the pineapple pattern I used for this post, start with a cherry and build your pineapple pattern around it. Start your pattern with the thinnest slices; save the thicker slices for last. If I did it again, I would start by lining the outside of the pan, triangle points facing in, overlapping the pieces, and pushing and bending the backs of the triangles to cover the inside curve of the bottom of the pan. Then spiral in making sure that the points will be exposed to the eventual top of the cake, in as much as possible. Use the thicker slices to re-ring the pan and create a nice side to the pineapple layer.
10. It takes about 3 minutes to cream the butter, ramping up to speed 6.
11. Taking the cake out of the pan is not for the timid. I recommend that you do it while the cake is still quite hot. Pour off the liquid if you wish, but I found that there was so little of it that it didn’t seem worthwhile. Run a knife in between the cake and the skillet. Place the cake plate upside-down, over the cake, and invert the entire thing. When it comes time for the flip, don’t go slowly … don’t try to do it quickly in a literal sense, just do it very deliberately. You can center the cake by tilting the plate, and you can pretty up the sides – if need be – with a large spatula.
12. You can leave the cake at room temperature for quite a while, but eventually, it’s got to go in the fridge.

I really like this cake. I’ve made it several times and have always been pleased. The fresh pineapples kills. I do wish for a bit more cake. Nicely done, Martha’s minions: (4 / 5)

Want to fit Fresh Pineapple Upside-Down Cake into a Hawaiian-themed menu? Follow this link.

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