Pineapple Upside Down Cake

Every baker has those times when you make something simple and yet achieve greatness. Enter this insane, off-the-hook-never-try-another-recipe-again pineapple upside down cake. Yes, it was so perfect that I will toot it's horn like that because it deserves every second of the glory. This cake is downright delicious with all the brown sugar caramel goodness nestled around fresh sweet pineapple pieces atop golden, moist cake. This is it folks. Serve this warm with a scoop of vanilla ice cream and you will be a certified kitchen rock star.

Pineapple upside down was not something I grew up eating. Most versions have canned, rubbery pineapple with maraschino cherries dotted all over the top. Sometimes they are dry and don't have much flavor. It reminds me of yellow wall paper, vinyl chairs and jello molds. It kind of freaks me out. I don't know why. This version though, is all class. You use fresh pineapple, first of all, which improves the flavor and texture ten fold. Then you make the caramel sauce, which takes 5 minutes and tastes like heaven. Then the cake you spoon on top of the whole she bang is thick, and flavored with fresh pineapple juice and rum. Once baked, the crumb of this thing is perfect. I might be overusing the word "perfect" but I don't care. This is my new favorite dessert!

I didn't have pineapple juice on hand but I did have a can of crushed pineapple, so I ended up straining the liquid from the can and using that. It worked great. This recipe originally came from Smittenkitchen.com. I love that site.

Pineapple Upside-Down Cake
Adapted from Gourmet, February 2000

Topping:

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

Batter:
1 1/2 cups all-purpose flour
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. If you lack a cast-iron skillet of this size, make the caramel in a small pot and scrape it into the bottom of a similarly-sized cake pan. (I used a 9″ cake pan in the pictures above.)

Preheat oven to 350°F.

Make topping:

Cut pineapple crosswise into 3/8-inch-thick pieces. Melt butter in skillet. Add brown sugar and simmer over moderate heat, stirring, four minutes. Remove from heat. Arrange pineapple on top of sugar mixture in concentric circles, overlapping pieces slightly.

Make batter:

Sift together flour, 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, one 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 40-45 minutes. Let cake stand in skillet five 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.

Do ahead: Cake may be made one day ahead and chilled, covered. Bring to room temperature before serving.

I used the rum that is called for in the cake but did not sprinkle the rest over the top since little kids were going to be eating this as well as adults.