I'm fairly certain I have never had pineapple upside down cake in my life, so I'm not really sure why I couldn't stop thinking about making pineapple upside down cupcakes for about two weeks straight. Seriously, it made no sense. I wasn't even sure what they would taste like...but I KNEW I wanted to eat them!
I found a recipe for pineapple upside down cake in my Better Homes and Gardens cookbook and thought that it would be perfect. I also knew that I wanted to use a glaze recipe from the same cookbook for the frosting.
The most complicated thing about this recipe was flipping the cupcakes over so that the butter/brown sugar/pineapple combination could seep into the cake. I have wire racks for cooling baked goods, but I didn't want to cool the cupcakes upside down on a wire rack. I didn't want the imprints from the rack on my beautiful cupcakes.
Instead, I turned the cupcakes upside down on a flat cookie sheet. This was also problematic. The cake from the top of the cupcakes got stuck to the cookie sheet. The lesson I took away from this was that I should have lined my pans with waxed paper. I didn't really mind the missing cake on the top of the cupcakes, though...it just provided the perfect little divot to fill with frosting!
Oh, another lesson I learned from this recipe is that the butter/brown sugar/pineapple combination is HOT when you take the cupcakes out of the oven. As I was pulling one of the cupcakes out of its pan, a little of the melted mixture got onto my finger...and I promptly dropped the cupcake on the floor.
I was really happy with the way these cupcakes tasted, but I have to admit that I wasn't prepared for how they ended up looking. You see, once the melted mixture seeps into the cooked cake, there is an empty space at the bottom of the cupcake liner for the cake to sink down into. I didn't really like the sinking cupcakes. However, they were delicious...so it wasn't THAT big of a deal!
Pineapple Upside Down Cupcakes
2 tablespoons butter
1/4 cup brown sugar
1 tablespoon water
1 8-ounce can pineapple chunks
1 1/2 cups all-purpose flour
2/3 cup granulated sugar
2 teaspoons baking powder
2/3 cup milk
1/4 cup butter, softened
1 teaspoon vanilla
- Preheat the oven to 350 degrees Fahrenheit. Place to 2 tablespoons butter in a large saucepan and put the pan in the oven until the butter melts. Remove from the oven and stir in brown sugar and water.
- Put liners in a cupcake pan (unless you make a double batch...then you should use two cupcake pans and make 24 cupcakes).
- Spoon equal amounts of the butter and brown sugar mixture into the bottom of each cupcake liners and then arrange pineapple chunks in the brown sugar/butter mixture (I used 4 chunks per liner).
- In a medium mixing bowl stir together flour, granulated sugar,and baking powder. Add milk, 1/4 cup butter, the egg, and vanilla. Beat with an electric mixer on low speed until combined. Beat on medium speed 1 minute. Spoon batter into the cupcake liners, filling each liner about 3/4 full.
- Bake 25-30 minutes or until wooden toothpick inserted in center of a cupcake comes out clean.
- Cool in pan for five minutes then remove cupcakes from your pan and flip them onto a cookie sheet lined with waxed paper to finish cooling.
Powdered Sugar Icing (I call this glaze)
1 cup powdered sugar
1/4 teaspoon vanilla
1 tablespoon milk
- In a small bowl combine powdered sugar, vanilla, and 1 tablespoon milk. Stir in additional milk, 1 tablespoon at a time, until icing reaches drizzling consistency (I'm fairly certain I only made one recipe of the icing for 24 cupcakes).
- After your cupcakes have cooled, flip them over so they are right-side up again and drizzle them with icing. I topped each cupcake with a pineapple chunk!