Pineapple Upside Down Cake

Pineapple Upside Down is one of my favorite cakes, if not my favorite!
I believe I first saw this cake when I was probably 10 or 11 years old on TV, being made by Sanjeev Kapoor. That used to be a time before the internet, and I would sit in front of the TV with pen and paper writing down the ingredients and procedure. Who does that anymore?
I took the recipe to my mom and we made it together. And our family loved it!! I eventually lost that recipe. But now we have the internet, and I found a good recipe of Epicurious.

Pineapple Upside Down Cake begins with melting butter with brown sugar until it starts to caramelize. This mixture is then poured into a cake pan and fresh pineapple slices (or you can use canned pineapple slices) are placed on top. If you like you can also garnish the top with maraschino cherries or candied red cherries (as shown in picture). A buttery cake batter is then poured over the pineapple slices and the cake is baked until golden brown. Once the cake cools, it is inverted onto a cake platter so the top of the cake features the pineapple slices that have become wonderfully soft and sweet from absorbing all that delicious caramelized sugar.

This is also one of the first cakes I baked after moving to the US, and my husband devoured it!
The second time I made it was a complete disaster, I'm guessing because I got a 'stick' of butter wrong and used 2, thinking I had half sticks. I didn't make it for a long time after that.
This spring, I came across a huge line of fresh pineapples at our local farm. I decided to buy one, as they come in really handy for snacking at the office. My husband however wanted the cake, so I decided to bake him one again. It turned out pretty close to the first time I tried it.
The recipe on Epicurious uses a cup of sugar, but I reduced it to 3/4 cup because I read many reviews suggesting it, and also I don't have a big sweet tooth. That was perfect for us. But if you like it sweet, go with 1 cup. Also, many reviews said that 3 tsp of cardamom powder was too much, or too overpowering. I used all 3 tsp since we love the flavor (we're Indians, duh!) and I thought it compliments the pineapple. If you don't like cardamom, then reduce it to 1.5 or 2 tsp, and you will get a more subtle flavor.
Also the recipe suggests you make this in a 10-inch cast iron skillet. I did not have one, but I highly recommend using it if you have. It will help get the pineapples nice and caramelized.
I used a 9 inch springform, which I regret because the caramel was oozing out the sides. I remedied it in time by wrapping the pan with aluminum foil. But next time I would use a regular cake pan, or hopefully a cast iron skillet.

Ingredients:

For topping:
1/2 medium pineapple, peeled, quartered lengthwise, and cored
3/4 stick unsalted butter
3/4 to 1 cup packed light brown sugar
5 or 6 maraschino cherries (optional)

For batter:
1 1/2 cups all-purpose flour
2 to 3 teaspoons ground cardamom
2 teaspoons baking powder
1/4 teaspoon salt
3/4 stick unsalted butter, softened
1 cup granulated sugar
2 large eggs, at room temperature
1 teaspoon vanilla
1 tablespoon dark rum
1/2 cup unsweetened pineapple juice
2 tablespoons dark rum for sprinkling over cake (Black Seal or Myers would work great!)

Special equipment:
a well-seasoned 10-inch cast-iron skillet

Method:

Preheat oven to 350°F. Butter the cake pan.

Make topping:
Cut pineapple crosswise into 3/8-inch-thick pieces. Melt butter in skillet. Add brown sugar and simmer over moderate heat, stirring, 4 minutes. Continue cooking, without stirring, for a few more minutes or until bubbles just start to appear around the outside edges of the mixture (the sugar starts to caramelize). Then remove from heat, and pour into your prepared cake pan. Arrange pineapple on top of sugar mixture in concentric circles, overlapping pieces slightly. You can also cut the pineapple into semi-circles and arrange them like in the photo below (taken when I made it the first time). I also arranged a few halved maraschino cherries upside down, for added color coz I had them lying around. But this is purely optional.
A traditional method is to have the whole pineapple rings arranged in a circle with a marschino cherry in the center of each ring. I find this pretty but there's a lot of wasted space and you may not get enough pineapple with every bite.
Note: The original recipe asked for 3/4 cup brown sugar. I used 3/4 cup initially but found there was still a lot of butter, so I added another 1/4 cup of brown sugar. What you're looking for is a sticky caramel sauce.

Make batter:
Sift together flour, cardamom, 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.)
Tip: If you dont have a sifter for the dry ingredients, just combine them all in a bowl using a wire whisk.

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.

This cake may be made a day ahead and chilled, covered. Bring to room temperature before serving.