Pineapple Upside-Down Cake

This is my first post from the Land of Aloha, where I am currently staying for a few months.  For my first Hawaiian recipe, I decided to try two versions of a favorite retro pineapple recipe:  Pineapple Upside-down cake.  I came upon this recipe on the food network for a pineapple cake that uses fresh pineapple and wondered how it would measure up to a cake made from a mix using canned pineapple.  Fresh pineapples seemed a bit cheaper in the islands than they are on the mainland, so the prices on this post may be somewhat skewed.  For the cake made from a mix, I used Pillsbury pineapple flavored cake mix and followed the directions on the box, using Dole canned pineapple rings.  The homemade cake  was a slightly modified version of the one I linked to above by Emerile Lagasse.  I used all all-purpose flour in my recipe and plain whole milk in place of buttermilk.  Also, I only had an 8-inch skillet available, so I just filled it 2/3 full of batter and baked the cake a few extra minutes.  Here’s the recipe I used:

Pineapple Upside-Down Cake

If you don’t have rum around (as I usually don’t) just use 2 teaspoons of vanilla instead of 1 1/2, or try using a tablespoon of pineapple juice in place of the rum.

Makes 1 10-inch Cake


1/2 ripe medium pineapple, cored and cut into 1/2 inch rings

3/4 cup butter

3/4 cup light brown sugar

2 cups all-purpose flour

1 teaspoon baking powder

1 teaspoon baking soda

1 cup granulated sugar

2 eggs

1 cup milk

1 1/2 teaspoons vanilla extract

1 Tablespoon dark rum

1.  Melt 4 Tablespoons of butter in a 10-inch cast iron skillet.  Stir in the brown sugar and bring to a simmer.  Arrange the pineapple rings over the butter/sugar mixture in the skillet and continue to cook for 2 more minutes, until bubbling and dark brown.  Set aside to cool while making the cake batter.

2.  Preheat the oven to 375 degrees.  In a medium mixing bowl, mix together the flour, baking soda and baking powder.  With an electric mixer, cream together the butter and granulated sugar.  Add the eggs, one at a time, and mix until just combined.

3.  Add the flour mixture a little at a time, alternating with the milk until all the milk and flour is incorporated.  Stir the vanilla and rum into the batter.  Pour the batter over the pineapple rings in the skillet.  Bake in the preheated oven for about 30 minutes, or until a toothpick inserted in the center comes out clean.  Serve warm with whipped cream or ice cream and maraschino cherries on top.

Ingredients measured out for Pineapple Upside-Down Cake

Pillsbury Pineapple cake batter

Pillsbury Pineapple cake batter

After both cakes came out of the oven, I served several tasters a little of each cake, topped with whipped cream and I was surprised at people’s reactions.  Out of six tasters, opinion was split pretty much in half over which pineapple upside-down cake was better.  Some preferred the sweeter, lighter taste of the cake made from a mix, while others liked the dense, mild homemade cake.  I personally liked the homemade cake with fresh pineapple because it was less sweet than the one made from a mix, and both the cake and pineapple were firmer in texture than the Pillsbury cake.   I thought the homemade cake had more the feel and taste of a pound cake while the Pillsbury cake was similar to a light, yellow birthday cake.   In terms of time and cost, both these cakes were pretty similar.  They both took around an hour to make, with the homemade cake taking a little longer, and both cost about $4.50 to make.

Homemade Pineapple Upside-down Cake

Cost:  $4.40

Time:  1 hour 10 minutes

Pillsbury Pineapple Upside-Down Cake

Cost:  $4.61

Time:  45 minutes

Bottom Line: This one basically comes down to personal preference with no clear winner.  If you like pound cake and pineapple, then I think you’ll love the homemade recipe in this post.  However, if you like the lighter texture and sweeter flavor of a yellow cake, then the Pillsbury pineapple cake mix may be more to your taste.  Either way, this classic dessert is a great end to a light, summery meal.

Homemade pineapple upside-down cake on the left, from a mix on the right

Homemade pineapple upside-down cake on the left, from a mix on the right