Pineapple Upside Down Cake

February 8, 2013

Guess what my strangest pregnancy craving has been?

I have not had this dessert in, oohhh, about 20 years. Seriously.  When is the last time you have seen this at a bake sale or a pot luck?  But when I passed ringed pineapple cans at the store, a not so quite voice in my head said, PINEAPPLE UPSIDEDOWN CAKE.

Well.  I guess cravings are not brought on by  a) the power of suggestion or b) anything rational.

But this craving did not lead me astray, because this cake is unbelievably delicious.  Seriously! Why have I not had this more often?!?!  If you have never had this cake, the bottom makes this crazy good carmel sauce that is made by starting the base with melted butter and brown sugar:


Then you place rings of pineapples and cherries, which the kids were more than happy to do, since they got to fight for the leftovers in the cans:

Then you make a super-simple batter and spread over this:

Then you bake it for 50-55 min. While it is still hot you flip it over and get this:


The pineapple juices make their own caramelization, then the butter and brown sugar make a second kind of carmel, soooo, you do the math.  Double carmel.  Which is what they might as well call this, double carmel cake.  But Pineapple Upside Down Cake is fun to say too. Also, cooking with shortening (while bad for you, sure) makes the cake the exact texture of a Twinkie, so if you are going through any withdrawal on the Twinkie front, this should help you.

My 5 year old daughter just walked up to me while typing this, saw these pics and said, “Oh, I LOVE that cake.” Enough said. If you live in New England, make it fast, because the snow+60 mile an hour winds are coming and you need to eat this tonight.


Pineapple Upsidedown Cake (for a printer version, click here)



1/4 cup butter or margarine

2/3 cup packed brown sugar

9 slices pineapple in juice (from 14-oz can), drained

9 maraschino cherries without stems, if desired

1 1/3 cups Gold Medal® all-purpose flour

1 cup granulated sugar

1/3 cup shortening

1 1/2 teaspoons baking powder

1/2 teaspoon salt

3/4 cup milk

1 egg



  1. Heat oven to 350°F. In 9-inch square pan, melt butter in oven. Sprinkle brown sugar evenly over melted butter. Arrange pineapple slices over brown sugar. Place cherry in center of each pineapple slice.
  2. In medium bowl, beat remaining ingredients with electric mixer on low speed 30 seconds, scraping bowl constantly. Beat on high speed 3 minutes, scraping bowl occasionally. Pour batter over pineapple and cherries.
  3. Bake 50 to 55 minutes or until toothpick inserted in center comes out clean. Immediately place heatproof serving plate upside down over pan; turn plate and pan over. Leave pan over cake a few minutes so brown sugar mixture can drizzle over cake; remove pan. Serve warm. Store cake loosely covered.

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