I originally adapted this cake from The Unofficial Mad Men Cookbook for a “Mad Men” series premiere party. I wanted to make something kitschy and quintessentially ‘50s/’60s, and the cake, with its decoration of maraschino cherries, seemed perfect. Imagine my surprise when it turned out to be one of the best cakes I’ve ever made, and one of my most trusted recipes. If I am baking for any special occasion where I don’t want the risk of a messed-up dessert, I always make this cake, and it always gets rave reviews. The tartness of pineapple makes it the perfect fruit for an upside-down cake, playing off of the sweet, caramelized topping. And the genius of this recipe is the reserved pineapple juice that you add to the batter, which gives the cake a lovely hint of tanginess that will keep you reaching for another piece. If you want to use fresh fruit, go for it, but make sure you have reserved pineapple juice! I fiddled around with the original recipe, reducing the amount of sugar in the cake, using salted butter for the caramel topping, and adding some pineapple pieces to the batter itself, which also keep things moist. I also add a splash of rum to my version, but you can leave that out and save it for the ‘60s style cocktails!

This cake batter is very dependable, and can be used by itself or with any other fruit, if you’re not a fan of pineapple or canned foods. Apricots would be nice in summer, and apples and pears are always a safe bet for an upside-down cake. If you do use a different fruit, replace the pineapple juice with some orange juice or apple juice.

Pineapple Upside-Down Cake
Serves 10-12

INGREDIENTS

Pineapple Topping
4 tablespoons salted butter
3/4 cup brown sugar
1 can sliced pineapple in it’s own juice (save the juice)
pecan halves (optional)
maraschino cherries/raspberries (optional)

Cake
10 tablespoons softened butter
1 cup granulated sugar
2 eggs
2 cups all-purpose flour
3 teaspoons baking powder
1 teaspoon salt
1/2 cup buttermilk (or 1/2 milk with 1/2 tsp of vinegar)
1/4 cup of pineapple juice from can
1 teaspoon vanilla extract
1 teaspoon rum or rum extract
leftover pineapple from can

PREPARATION

Preheat oven to 350 degrees.
Line a 10-inch cake pan with parchment paper or aluminum foil (in the picture, I used a 9x13 pan. If you do this, the cake to topping ratio will be more 1 to 1. Reduce the baking time to 25-30 minutes) .
For the topping: Melt butter and stir in brown sugar, cooking for 30 seconds-a minute until it dissolves. Pour sugar mixture into bottom of cake pan, distributing evenly.Lay pineapple slices on top and decorate with maraschino cherries or raspberries and pecans if you'd like.
For the batter: In a small bowl, combine flour, baking powder, & salt.
In a measuring cup, combine buttermilk, pineapple juice, vanilla and rum.
Cream butter and sugar. Beat in eggs. Add in any leftover pineapple pieces–you can break them up beforehand, or let the beaters do the work. Alternate adding flour mixture and buttermilk mixture, beating well.
Spread batter over pineapple pieces.
Bake for 45-50 minutes, or until a toothpick inserted in the center comes out clean.
Let the cake cool for 15 minutes before inverting and peeling off parchment paper or foil.