Pineapple Upside-Down Cupcakes

I’m pretty really into Mad Men. I’ve been waiting for the season 5 premiere for what seems like a lifetime. (Seriously, Man Men people?! 15 months between seasons?! Don’t do that.)
My friend Leah and I were so pumped for the premiere that we wanted to do something special. We’re getting together tonight to watch it (because…why would I want to watch it alone?), and we decided to have TV dinners (very 60s) and I knew I had to bring something fitting for dessert. I came across these cuties on Pinterest, and though I’m not all that into Pineapple Upside-Down Cake, they looked so cute and seemed so very apropos, so I knew I had to make them. They are so easy and so cute and if Pineapple Upside-Down Cake is your deal, you’ve got to give these a shot.

Pineapple Upside-Down Cupcakes
Makes 12 cupcakes

Cake Ingredients:
6 tablespoons butter
1/2 cup milk
1 cup flour
1 1/2 teaspoons baking powder
1/4 teaspoon salt
2 eggs
3/4 cup sugar
1/2 teaspoon vanilla

Topping Ingredients:
6 tablespoons butter
3/4 cup brown sugar
6 maraschino cherries
1 (20 ounce) can pineapple rings

Heat the oven to 350 degrees. Place the butter and milk for the cake into a small saucepan over medium heat. Warm the mixture, stirring occasionally, until the butter melts. Transfer the mixture to a small bowl to cool.
Meanwhile, prepare the pineapple topping. Into each cup of a 12-cup muffin tin, place 1/2 tablespoon butter (unmelted), and sprinkle with 1 tablespoon of the brown sugar. Place the tin into the oven until the butter melts, about 3 minutes.
Halve each cherry, and cut the pineapple rings into quarters. Place a cherry half, sliced side up, into the center of each muffin cup. Lay a pineapple quarter on each side (2 quarters per cup).
Finish making the batter. In a medium-sized bowl, combine the flour, baking powder, and salt and stir with a fork until the ingredients are blended. In a large bowl, whisk the eggs, sugar, and vanilla until smooth. Add the flour mixture to the egg mixture and stir until the flour is fully incorporated. Add the cooled milk/butter mixture and stir until smooth.
Pour the batter into the muffin tin, dividing it evenly among all the cups. (You may have some left over. I used all the batter and filled them too full. Some of the cups overflowed a bit. Try not to make the same mistake, as it will make it more difficult to take them out after they cool.)
Bake the cupcakes about 25 minutes (I had to do 30), or until the cakes are lightly browned, dry around the edges, and pull away from the pan a little.
Let the cupcakes cool in the pan for about 5 minutes, then run a butter knife around the edges to loosen the cakes. Place a cookie sheet over the top of the pan and invert it, so that the cupcakes are on the cookie sheet. Transfer to a cooling rack to cool completely. Serve at room temperature.






**On an unrelated (sort of) note, I’m moving my blog! Please continue to follow me at Thanks so much!

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