I am constantly inspired by everything around me but more than anything, I am inspired by my heritage and family traditions.  Pineapple upside down cake is such a classic Southern dish that was served countless times in my house.  I was always so mesmerized by the creation of this dessert as a child.  I would watch the cake bake in the oven not knowing the unique surprise beneath that awaited me.

When my mom flipped the cake over to reveal the gorgeous decorative pineapple and cherry topping, I would stare in awe.  The cake just seemed so special, so sacred.  

Sometimes playing around with sacred childhood memories can be dangerous but I always loved taking the recipes I grew up with and making them my own, which now brings me to these little lovelies.  They are such wonderful cupcakes.

The base is a moist sour cream cake mildly flavored with rum to give it an extra kick.  Topping it with a pineapple buttercream made it even better but the real surprise is what is underneath.  Little small chucks of pineapple ready to eat with every bite.  

Now don't you want some of that? 


For the Cupcake Batter

  • 1 stick unsalted butter, softened
  • 1 cup granulated sugar
  • 3 large eggs
  • 1 tablespoon oil
  • 1 1/2 cup cake flour
  • 1/4 teaspoon salt
  • 1/4 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/2 cup sour cream
  • 2 teaspoons vanilla extract
  • 1 teaspoon rum

For the bottom of the cupcakes

  • 1 cup brown sugar
  • 1 can (8.25 ounces) pineapple bits, drained (save the juice) or fresh pineapple if in season
  • 1 stick melted butter

For the buttercream

  • 1 stick unsalted butter, softened
  • 4 ounces cream cheese, softened
  • 2 cups confectioner's sugar
  • 2 tablespoons crushed pineapple 
  • 1 teaspoon vanilla extract 
  • 1-2 tablespoon pineapple juice 


For the Cake Batter 

Preheat oven to 350 degrees.
Add butter and sugar to bowl of a mixer and beat on medium high until well incorporated and light and fluffy (about 4-5 minutes).  Next add in eggs one at a time then oil and beat until well mixed.  Sift together cake flour, salt, baking powder, and baking soda.  In a separate bowl, add sour cream, vanilla extract, and rum.  Alternate flour mixture and sour cream mixtures to mixer, ending with the flour mixture, and beat each addition until batter is well mixed without overmixing.

To assemble cupcakes,

Line muffin/cupcake pans with cupcake liners.  Spoon 1 teaspoon of melted butter into the bottom of each liner.  Top the butter with 1 teaspoon of brown sugar.  Then spoon 1 teaspoon of crushed pineapple over the brown sugar and spread out on the bottom of the liner.  

Next using a ice cream scooper, add cake batter to each cupcake liner over the crushed pineapple.  The liner should be filled about 3 quarters of the way.   Bake for 20-24 minutes or until a toothpick inserted into the center of the cupcakes comes out clean.

Allow the cupcakes to cool in the pans for 10 minutes then remove the cupcakes from the pans and place them on a cooling rack to cool completely.

For the buttercream

While cupcakes cool, add butter, cream cheese and confectioners sugar to bowl of a mixer and mix on high for 2 minutes.  Next add crushed pineapple, vanilla extract and pineapple juice in small amounts to frosting (make sure frosting isn't too loose as pineapple juice is added) and mix until ready to frost.  Frost each cupcake once it is completely cool and enjoy!  Makes 24 cupcakes.

Jocelyn Delk Adams is the founder of Grandbaby Cakes, a food blog inspired by her grandmother that is devoted to classic desserts, modern trends and showcasing the pastry and sweets field in an accessible way. She hopes to inspire a new generation of bakers and dessert enthusiasts to learn to bake and not feel guilty about enjoying dessert.  Visit her at www.grandbaby-cakes.com