Turn That Frown Upside Down (Cake)

Pineapple Upside Down Cake

Pineapple Upside Down Cake

If you’re ever feeling a lil bit grumpy, I have just the thing for you! Brown sugar caramel, pineapple, and maraschino cherries, soaking into a cake rich with butter and sour cream…if it doesn’t make you smile, it will at least make your tummy happy! Plus, how fun is it to pull a regular-looking cake out of the oven, turn it out of the pan, and BAM! All kinds of stuff happening there! The beautiful browned pineapple and bright cherries, the gooey caramel oozing down the sides, it’s like finding a treasure hidden in your oven.

I love the look of a pineapple upside down cake, and I’m a huge fan of caramelized anything, but my favorite part of this recipe is actually the cake. It contains sour cream and a lot of butter. It’s dense but tender, and brings to mind the flavor of a decadent pound cake, with the added flavors of brown sugar and pineapple layered over the top.

Pineapple Upside Down Cake 2

This isn’t what I would consider an “everyday/anyday” cake (mostly because I usually don’t have pineapple rings on hand!), but it’s simple enough to put together, much easier than the presentation of the cake suggests. But even if you do keep pineapple rings stocked in your pantry, I do not recommend that you make this regularly. You may think it’s strange for me to discourage repeated use of a recipe on this site, but this cake absolutely has got to be bad for you. It has 3 sticks of butter in it. And a lot of sugar. I don’t think the “…but it has fruit in it!” health claim works in this situation, and I’m pretty sure your doctor will send me hate mail if you make this too often.

Turn That Frown Upside Down (Pineapple Upside Down Cake)
Prep time: 
Cook time: 
Total time: 
Serves: 10-12
Brown sugar-caramel, pineapple, and maraschino cherries soaking into a cake rich with butter and sour cream.
  • 1 C firmly packed brown sugar
  • ½ C butter
  • 1 can (20 oz.) pineapple rings
  • 5-6 maraschino cherries
  • 1¾ C granulated sugar
  • 1 C butter, room temperature
  • 4 eggs
  • ¾ tsp vanilla
  • 2 C Bob's Red Mill 1-to-1 Baking Flour
  • ¾ tsp baking powder
  • ½ tsp salt
  • ¾ C sour cream
  1. In a small saucepan, melt the butter and brown sugar over medium heat until the sugar is dissolved.
  2. Stir continually for several minutes until the mixture is bubbly.
  3. Pour into a non-stick 10-inch diameter cake pan, and swirl to coat the bottom.
  4. Arrange the pineapple slices in a single layer, and place a cherry in the center of each slice.
  1. Preheat oven to 325 degrees.
  2. Beat sugar and butter until light and fluffy.
  3. Add eggs, one at a time, mixing well after each one.
  4. Beat in vanilla.
  5. In a separate bowl, lightly whisk together the flour, baking powder, and salt.
  6. Add half of the dry ingredient mix to the butter/sugar/egg mixture, followed by half of the sour cream, mixing well after each addition.
  7. Repeat with second half of flour mixture followed by second half of sour cream, making sure everything is well-blended.
  8. Spread batter over the caramel and pineapple in pan.
  9. Bake for 1 hour to 1 hour 45 minutes, until toothpick inserted in center comes out clean.
  10. Cool in pan for 10 minutes, then carefully turn out onto a platter.


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