I have a thing for pineapple. I enjoy it in my cake and in my cocktails. I love it in fried rice and on pizza. Pineapple is the perfect fruit for both sweet and savory applications. It also transcends me immediately to some of the lovely tropical islands I've had the pleasure of visiting.
I'm sure everyone has had pineapple upside-down cake at some point in their cake-eating careers. It's typically made with tinny pineapple rings out of a can, glow-in-the-dark artificial red maraschino cherries, and many times a box cake mix. This is sadly the usual, but not in my kitchen. I knew that in making a pineapple upside-down cake, it would be better than all the rest.
I would cut fresh pineapple, make my batter from scratch, omit the kitschy cherries, and even spike the whole thing with some delicious rum. Because rum and pineapple are just made for each other. I actually used some nice spiced rum from Cane Garden Bay in Tortola (British Virgin Islands). My family took a trip there last year and discovered this delicious rum... made by a local woman in her bathtub. It's better than it sounds. Trust me :)
The cake as a whole is just fantastic. My sister claims it's officially her new favorite cake and insists I make it for her upcoming birthday. It was easily one of the most popular desserts I served recently at my nephew's Christening. Who doesn't love a really well-made, fresh pineapple upside-down cake?
**All photos updated on 3/11/17**
Pineapple Upside-Down Cake
Adapted from Gourmet, February 2000 (via Smitten Kitchen)
Makes 1 cake
1/2 medium pineapple, peeled, quartered lengthwise, and cored
3 oz (6 tablespoons) unsalted butter
3/4 cup packed light brown sugar
1 1/2 cups all-purpose flour
2 teaspoons baking powder
1/4 teaspoon kosher salt
3 oz (6 tablespoons) unsalted butter, room temperature
1 cup granulated sugar
2 large eggs
1 teaspoon pure vanilla extract
1 tablespoon dark rum
1/2 cup unsweetened pineapple juice
2 tablespoons dark rum for sprinkling/brushing 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, such as a 9-inch round cake pan.
Preheat oven to 350 degrees 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. Alternatively, pour sugar mixture into cake pan and arrange pineapple slices on top.
Make batter: Mix 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.
Spoon batter over pineapple topping and spread evenly. Bake cake in middle of oven until golden and a tester comes out clean, about 40 to 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 or brush 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.