Chef John's Pineapple Upside-Down Cake

Chef John's Pineapple Upside-Down Cake

Chef John 21760

"This iconic American dessert looks like a simple, rustic fruit cobbler when it comes out of the oven, all browned and bubbling, but a few minutes later, when it's turned over and that gloriously caramelized surface is revealed, it becomes so much more."


1 h 20 m servings 263 cals
Serving size has been adjusted!

Original recipe yields 12 servings



  • Calories:
  • 263 kcal
  • 13%
  • Fat:
  • 12.3 g
  • 19%
  • Carbs:
  • 35.9g
  • 12%
  • Protein:
  • 2.7 g
  • 5%
  • Cholesterol:
  • 47 mg
  • 16%
  • Sodium:
  • 274 mg
  • 11%

Based on a 2,000 calorie diet

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  • Prep

  • Cook

  • Ready In

  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.
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  1. 71 Ratings


UNBELIEVABLE!! This cake is absolutely amazing and so easy to make. It was gone in 10 minutes at my house. Very earthy and fulfilling. I'll be making this again and again...It is "The perfect de...

So I watched the video of this recipe that was posted on the home page, and decided to try it...Had to improvise a bit (apologies to you review purists) used Capt. Morgans spiced rum and had no ...

Sorry- I thought the cake was dry. There are other recipes I find much more moist and have more flavour. The cardamom did not add the "special" element I thought it would.

I was surprised by this, because I expected the dough to be liquidy, as usual for cake. The dough was actually very thick, almost knead-able, even after I added a splash more of milk to try and ...

Great, reminds me of my mom's cast iron pineapple upside down cake. Only difference I have made in recipe is to use canned unsweetened pineapple slices with a maraschino cherry placed in the cen...

I was looking so forward to trying this recipe I even bought a cast-iron skillet! I don't know if I did something wrong (I can't see that I did), but it was disappointing. It looked pretty, just...

What no cayenne? Have not made yet just surprised to see Chef John and no cayenne pepper. i will updated tonight when i make it ****UPdate***This was a great cake, i only gave it 4 stars becaus...

This was quite good, but I'm sorry to say that I likes the box mix version my brother made for me better. He used a yellow cake mix (substituting applesauce for the oil - cake was really moist ...

i like my betty crocker recipe better moist i will not make this again.. but fun trying ..