Pineapple Upside Down Cake


I’m an early riser.  Usually up between 5 am and 6 am.  I don’t leave for work until around 9:30 so I have a lot of time to kill.   Yesterday morning I decided to bake something.  Pineapples were on sale this week for $2.97.  Beautiful ripe golden pineapples.   What better to bake than a Pineapple Upside Down Cake.

There are lots of recipes to choose from, but one that I have seen on a regular basis recently is Thomas Keller’s version.  I found a great picture of his cake on a number of blogs including Jun-Blog, Sea Salt With Food and Sweet Cakes.

 Many Pineapple Upside Cake recipes call for baking in a cast iron pan.  Thomas Keller’s recipe specifies a silcone cake pan.  This apparently makes it easier for those that are uncomfortable with tipping a cake, dripping with hot caramel, out of a cast iron pan and on to a plate.

I followed the recipe almost to a “T” except for two things. I skipped the rum and added more vanilla to the “smear” and I baked my cake in a cast iron skillet.


Moe enjoyed a piece of warm cake with his coffee.

Pineapple Upside-Down Cake


Pan Schmear
8 Tbsp (1 Stick; 4 oz) Unsalted Butter, at room temperature
1 ½ Tbsp Honey
½ tsp Dark Rum
1 Cup Packed Light Brown Sugar
¼ tsp Vanilla Paste or Pure Vanilla Extract
Sea Salt

1 Gold (Extra-Sweet) Pineapple

1 1/3 Cups Cake Flour
2 tsp Baking Powder
8 Tbsp (1 Stick; 4 oz) 

Unsalted Butter, at room temperature
½ Cup Plus 2 Tbsp Granulated Sugar
½ tsp Vanilla Paste or Pure Vanilla Extract
2 Large Eggs
1 Tbsp Plus 1 tsp Milk


Preheat the oven to 350˚F.

In the bowl of a stand mixer fitted with the paddle, combine the butter, honey, rum, brown sugar, and vanilla and beat until smooth and well blended. Spread 1/3 cup of the schmear over the bottom of a 9-inch silicone cake pan. Sprinkle lightly with salt. (The remaining schmear can be refrigerated for up to 2 weeks or frozen for up to 1 month; bring to room temperature before using.)

Cut the top and bottom from the pineapple and cut away the peel. Cut the pineapple lengthwise into quarters, and cut off the core from each section. Cut each piece crosswise into ¼-inch thick slices. Beginning at the perimeter of the pan, make an overlapping ring of pineapple slices with the curved side facing out. Make a second ring inside the first one, overlapping the slices in the opposite direction, working toward the center of the pan.

Sift the flour and baking powder together; set aside.

Put the butter and sugar in the bowl of a stand mixer fitted with the paddle and mix on low speed to combine, then beat on medium speed for about 3 minutes, until light and creamy, stopping to scrape down the sides as necessary. Mix in the vanilla. Add the eggs one at a time, beating until the first one is incorporated before adding the second and scraping down the sides as necessary. Beat in the milk. Add the flour mixture in 3 batches, beating until combined.

Pour the batter into the pan and spread over the pineapple. Bake for 15 minutes. Rotate the pan for even browning and bake for another 20 to 25 minutes, until a cake tester or wooden skewer inserted in the center of the cake comes out clean. Cool the cake in the pan on a cooling rack for 20 to 40 minutes.

Run a knife around the edges of the cake, invert onto a serving platter, and serve warm. (Leftover can be stored at room temperature for up to 2 days.)

NOTE:  This cake would be even better with more sauce.   Next time I make it I’ll double the “Smear”.

Serves 8

18 Comments Add yours

  1. I haven't had a pineapple-upside down cake in ages!! This looks delicious. Copying this recipe! Thanks, Ann!

  2. Too funny! I was just commenting to a neighbor that I hadn't made an upside down cake in a while. I'm going to try this version!xoxo Pattie

  3. Karen says:

    Your cake looks so yummy! You're not only a great cook but great photographer. KarenLadybug Creek

  4. Linda says:

    This looks fabulous Ann…bookmarked and I will make this for Mike when he gets back from Brussels at the end of May…he loves Pineapple Upside down cake..I have not had it in ages…Gorgeous!L~xo

  5. Foodiewife says:

    This is a beautiful cake, indeed. I love my cast iron skillets, so that's how I'd make this. I buy pineapple on a regular basis, and it's high time I make this classic cake. Great recipe!

  6. I remember reading that the cast iron skillet was the best vehicle for this type of cake! Your cake is picture-perfect!

  7. Cathy says:

    One of my favorite desserts! And pineapples are at their best right now. I think I'll try using my cast iron skillet too and hope the fruit doesn't stick.

  8. Kathy Walker says:

    This is the cake that I always requested that mom make for my birthday! She added a few cherries on top for me. I think it is time to break out the cast iron skillet!

  9. Memória says:

    This looks so good. Oh goodness!! I want some now. I've never made any type of upside-down cake. I need to fix that pronto. I'm so glad you subbed the rum for vanilla. Now I know what I can do whenever I make this.

  10. oh yum! just made pineapple upside down cupcakes for my baking blog myself! cheers to that! :)

  11. Cherine says:

    Gorgeous looking cake!! I love this cake!

  12. lbrookscooks says:

    You should check out the article comparing Keller's version of a fried chicken dinner to Pioneer Woman's, including this cake. It's an interesting contrast. Your cake looks so good!

  13. Valen says:

    This cake looks so good! I'm also an early riser, it will never be any other way.

  14. Deana Sidney says:

    I'm making this puppy this weekend… It looks amazing and how can you go wrong with a Keller recipe???

  15. This looks amazing! Another excuse to use my cast iron :)/I'm giving away Ad Hoc At Home at my blog if you guys are interested:

  16. Anonymous says:

    I would NOT be able to cook without my huge collection of cast-iron. Trick is to keep them clean.If allowed to get grungy just take a fine grade of sandpaper scrub them then re-oil pan. It will be like new. I always use PAM.

  17. Unknown says:

    Noticed the price you paid for the pineapple in 2010. Amazing that I can occasionally find them sale priced for $1.99 to this day. Granted that's usually a whole pineapple, but often can find for $2.50 already cut and cored.

  18. Even today I very seldom find pineapples on sale for less than $2.99. They are more often in the $3.99 to $4.99 range.

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