Chef John’s Pineapple Upside-Down Cake

  4.0 – 109 reviews  • Pineapple Dessert Recipes

When this famous American dessert first comes out of the oven, all browned and bubbling, it just appears like a straightforward, rustic fruit cobbler. But after a few minutes, when it’s turned over and that gorgeously caramelized surface is revealed, it transforms into something much more.

Prep Time: 15 mins
Cook Time: 45 mins
Additional Time: 20 mins
Total Time: 1 hr 20 mins
Servings: 12
Yield: 1 (12-inch) cake

Ingredients

  1. ¼ cup butter
  2. ¾ cup light brown sugar
  3. 1 tablespoon pineapple juice
  4. 1 tablespoon dark rum (Optional)
  5. ½ small fresh pineapple – peeled, cored, and sliced
  6. ½ cup butter
  7. 1 ½ cups all-purpose flour
  8. ⅛ teaspoon ground cardamom
  9. ½ teaspoon salt
  10. 2 teaspoons baking powder
  11. ½ cup white sugar
  12. 1 large egg
  13. ½ cup cold milk

Instructions

  1. Preheat the oven to 400 degrees F (200 degrees C).
  2. Melt 1/4 cup butter in a 12-inch cast iron skillet over medium-low heat. Stir in brown sugar, pineapple juice, and dark rum. Cook over medium-low heat until sugar is dissolved and mixture is bubbling, about 5 minutes.
  3. Remove from heat and spread pineapple slices in a layer over the brown sugar mixture, completely covering the mixture. Set skillet aside.
  4. Melt 1/2 cup butter in small skillet over low heat until the butter begins to brown and release a nutty fragrance, about 5 minutes. Watch carefully, butter burns easily. Remove from heat and let cool for 10 minutes.
  5. Whisk together flour, cardamom, salt, baking powder, and white sugar in a large bowl. Whisk in egg and cold milk until just combined. Pour in melted butter and stir to mix thoroughly.
  6. Pour batter over the pineapple slices in the skillet; spread evenly to cover.
  7. Bake in preheated oven until the cake begins to bubble around the edges, the top is browned, and a toothpick inserted into the center comes out clean, about 30 to 35 minutes. Let cool in the skillet for 10 minutes.
  8. Loosen the cake from the skillet by running a knife around the inside edge of the cake. Invert a large plate over the top of the skillet and flip over, releasing the cake to show the pineapple slices on top.

Nutrition Facts

Calories 263 kcal
Carbohydrate 36 g
Cholesterol 47 mg
Dietary Fiber 1 g
Protein 3 g
Saturated Fat 8 g
Sodium 274 mg
Sugars 23 g
Fat 12 g
Unsaturated Fat 0 g

Reviews

Adam Bell
It’s a hit!
Thomas Petersen
Delicious!
John Sutton
We are BIG fans of Chef John!!! We bought a pineapple that wasn’t really great and it was either make something with it or throw it out. Made this DELICIOUS and easy recipe with it! Another 12 out of 10 for Chef John!
Timothy Hines
A big hit with my husband! His favorite dessert and super easy!
Luis Thomas
This was my first time ever trying out this type of cake, and also the first time I tasted a home made one like this. The cake was tasty, but a bit dry. I think I should have let it sit for a longer period of time until it cooled more. Also, my husband said that the top needed to a bit more crunchy (Not sure if this is actually how the cake is supposed to be or just his preference).
Anna Robinson
Not enough batter I think this either needs to be made in a 10” cast iron pan (I know most people have 12” pans) OR the batter needs to be doubled – there just isn’t enough cake!
Shannon Nguyen
This is the very best Pineapple Upside Down Cake I have ever tasted and the best I’ve ever made! AND I am a very good cook. Have been cooking since I was 9 and that was 60 years ago! I was concerned at first, that I had read the ingredient list wrong due to the amount of butter in the batter, but no! It works. It was so incredible, my husband loved it and daughter as well, And I will be making it for other holiday parties, and ask for it for my birthday cake in November! Thank you so much, Chef John, for such a lovely treat! PS I sprinkled some dried cherries on the brown sugar sauce for color, then broken canned pineapple rings – fresh was unavailable during my last pandemic shopping spree –
Joseph Mack
Loved this technique using a cast iron skillet. However the batter was too thick. I added more milk, 1/4 C or so. Next time I make this recipe, I will adjust recipe for high altitudes over 5000 ft. by decreasing the flour, extra milk and/ or pineapple juice to achieve a smooth batter.
James Cruz
It was a bit dry, next time more milk.
Tara Stanley
baked for 25 minutes, not dry-perfect! Thank you Chef John!
Melissa Hill
Outstanding! Be sure to watch the video for tips on ingredient combining and handling. My husband loves Pineapple USD Cake. He said this version was the best he had ever had. I agree. It was easy to make and didn’t last long! If you are feeding a crowd better make two! The dark rum cooks off leaving a hint of a taste that adds texture to the flavor. I followed the instructions exactly except I used dark brown sugar.
Dr. Matthew Mcclure
People commented a bit dry so I added one more tbls of juice as well as cut the flour down a tbls. it was perfecto! oh and added some frozen dark cherries on top of the pinnapple before cooking as well.
Jeffrey Webb
A Very easy, and fun, cake to make, so long as you have the equipment and the ingredients. Recommended for all.
Debbie Flores
I liked the flavor of this cake, however the cake batter didn’t have enough liquid in it and the cake came out dry and cracked. I guess I should have watched it closer and not baked it for the full time or maybe we just live in different climate than Chef John. Either way the flavor was there.
Cory Villarreal
made 2 right off the bat very good
Jake Banks
Substitute milk with buttermilk
Kristen Carlson
Outstanding great taste and totally moist
Michael Rodriguez
I did not use marjoram the first or second time I made this. When I made the second cake, I added coconut and almond flavoring to the brown sugar and butter mixture and the cake batter, too.
Jose Clements
Easy! Tasty!
Michelle Finley
Made this for my dad’s birthday since upsidedown pineapple cake is his favorite. Everyone who was there ate it and thought it was the best cake upsidedown pineapple they ever had. I myself thought it was delicous as well. To add a bit of appeal, I waited till the cake cooled down and sprinkiled powdered sugar on the top of the cake.
Tara Wilson
I followed the recipe exactly. The flavor was wonderful but I found the cake to be rather dry. I only baked it for 25 minutes. If I try it again, I think I will use a 10 inch skillet, increase the amount of the butter/brown sugar sauce and perhaps add some oil to the cake batter. As I said, the flavor was spot on, just a little dry.

 

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