Pineapple...SURPRISE!

My cousin Sara's birthday was last week and her daughter planned a surprise birthday party. When my uncle Dave called weeks ago to tell me about the party, I offered up my help. "I'll make dessert," I said. "What is Sara's favorite." I was up for anything. I assumed his reply would be cupcakes or pie or heck - even Crème Brûlée. "Pineapple Upside Down Cake," Dave said.

Huh? I had never made Pineapple Upside Down Cake (which I will from here forward refer to as PUDC). Heck, I'd never even eaten it!

I started some preliminary recipe research. There were thousands of recipes out there. Some used canned pineapple, some fresh. Some used cake mix, some made the cake from scratch. Argh - I didn't know where to start.

Sara and I were out at a bakery a week or so later and I asked her - slyly, like I wasn't doing recon for a recipe - "what is your favorite dessert?" PUDC, she replied. Really, I've never had it - tell me more. She proceeded to tell me how the best ones are made with fresh pineapple and in a cast iron skillet. Now I was getting somewhere.

I still was thrown off by the glut of recipes out there, so I posted a plea for help on Chowhound. Bingo - I got great tips! Out of all the ones I read, the one from Gourmet looked like it fit the fresh pineapple/cast iron skillet requirements best. It also includes Rum.

A kitchen rule I follow sporadically is that you shouldn't try a recipe out on guests that you haven't tried ever before. This coupled with the fact that Dave sent an email saying, "Sonja is making the official birthday cake" sent me to the store for pineapples.

The first attempt was a hit. Oh my gawd! This is PUDC?! Why have we never had this - Gavin and I exclaimed late one Sunday evening, as we scarfed down about half the cake. It was amazing. Sticky sweet and super pineapple-y.

Thankfully I work with a bunch of hungry honest people that will willingly eat food I make and critique it honestly if I ask. They loved the PUDC. I attempted the recipe a second time - for our friend Jason's birthday. He loved it too.

What I learned was that PUDC doesn't look great if you make it the night before. The top gets kind of soggy looking. Tastes great, but looks terrible. Fresh pineapple is a must, but it need not be totally ripe (unless it already is). The cooking time and sugar make up for any sweetness lacking in the fruit. I also substituted cinnamon & cloves for the cardamon in the original recipe. Not because I didn't like it, but because I didn't have it.

Pineapple Upside Down Cake
Adapted from Gourmet

For topping
1/2 medium pineapple, peeled, quartered lengthwise, and cored
3/4 stick unsalted butter
3/4 cup packed light brown sugar

For batter
1 1/2 cups all-purpose flour
1 1/2 teaspoons ground cinnamon
1/2 teaspoon ground cloves
2 teaspoons baking powder
1/4 teaspoon salt
3/4 stick unsalted butter, softened
1 cup granulated sugar
2 large eggs
1 teaspoon vanilla
1 tablespoon dark rum
1/2 cup unsweetened pineapple juice
2 tablespoons dark rum for sprinkling over cake
Special equipment: a well-seasoned 10-inch cast-iron skillet

Preheat oven to 350°F.

Make topping:
Cut pineapple crosswise into 1/2-inch-thick pieces. Melt butter in skillet. Add brown sugar and simmer over moderate heat, stirring, 4 minutes. Mixture should be thick and caramel-like. Remove from heat. Arrange pineapple on top of sugar mixture in concentric circles, overlapping pieces slightly.


Make batter:
Sift together flour, cinnamon, cloves, baking powder, and salt. Beat butter in a large bowl with an electric mixer until light and fluffy, then gradually beat in granulated sugar. Add eggs, 1 at a time, beating well after each addition. Beat in vanilla and rum. Add half of flour mixture and beat on low speed just until blended. Beat in pineapple juice, then add remaining flour mixture, beating just until blended. (Batter may appear slightly curdled.)

Spoon batter over pineapple topping and spread evenly. Bake cake in middle of oven until golden and a tester comes out clean, about 45 minutes. Let cake stand in skillet 5 minutes. Invert a plate over skillet and invert cake onto plate (keeping plate and skillet firmly pressed together). Replace any pineapple stuck to bottom of skillet. Sprinkle rum over cake and cool on plate on a rack.

Serve cake just warm or at room temperature.


So - the day of the party arrives. I borrowed my mom's cast iron skillet so I could make two cakes at once. I got an early start and made a total of four cakes.

The surprise went off without a hitch. Sara was totally surprised and the cakes were a hit. I was dying to know what she thought. She said, "seriously, this is SO GOOD!" Her reaction made it all worthwhile. Plus, I have a new favorite cake too.