Upside Down

Here's our cake. Don't you love my sister's new cake plate(from Williams-Sonoma,

Yesterday was National Pineapple Upside-Down Cake Day.
I’m not a slave to food holidays. So many of them were created by commercial interests. (I can find no evidence that Mr. Dole invented this one, and yet I can’t help but wonder…….)
Nevertheless, pineapple upside-down cake has long been a favorite of mine.
It’s a dessert with many associations. The pineapple itself has long symbolized hospitality and elegance.
To me fresh pineapple is a magical fruit—a perfect blend of sweetness and acidity. I know the pineapple we get in the northeast can’t compare with its cousins in their native climes. Nevertheless, if left to ripen for a few days a fresh pineapple can give us Yankees the illusion of living in a tropical paradise.
I generally eat the fruit plain—but I’ve been known to put it in fruit salad or salsa.
Pineapple upside-down cake is a simple comfort food I remember with joy from my childhood.
Even made with canned pineapple it delights eaters. When I worked as a demo cook at Bloomingdale’s I kept canned pineapple on hand for days on which I was uninspired. A quick batch of upside-down cake made even the most fussy of customers happy.
The cake is even better when made with fresh pineapple. To tell you the truth, the flavor isn’t terribly different. By the time you bake fresh pineapple pieces they taste a lot like canned ones. Nevertheless, I love having more substantial chunks in the cake than one can achieve with canned pineapple.
I think it would taste even better with a little rum added along with the vanilla, but I couldn’t find rum in the house so I don’t know for sure.
If you’re interested in the history of pineapple upside-down cake, take a look at the Food Timeline’s copious notes on this item, which include vintage recipes.
If you’re interested in making your family happy, bake this cake!

Pineapple Upside-Down Cake
for the upside-down topping:
1/2 stick butter (1/4 cup)
3/4 cup brown sugar (I used dark brown as that is what I had, but light brown might look prettier)
2 cups pineapple, cut into chunks
for the cake:
1/2 cup (1 stick) sweet butter at room temperature
1 cup sugar
2 eggs
2 teaspoons baking powder
1 pinch salt
1-1/2 cups flour
1/2 cup milk
2 teaspoons vanilla
Preheat the oven to 350 degrees.
First make the topping (which goes on the bottom!).
Melt the butter in a skillet—a 9- or 10-inch cast-iron skillet, if possible. Stir in the brown sugar and cook, stirring, until it melts and bubbles—3 to 4 minutes.
If you’re using the cast-iron skillet you may continue with the recipe at this stage and cook the cake in the skillet. If not, transfer the brown-sugar mixture into a 9-inch round cake pan. Spread it through the bottom of the pan. Arrange the pineapple pieces on top as artistically as you can.
In a separate bowl cream together the butter and sugar. Beat in the eggs, 1 at a time, beating well after each addition. Beat in the baking powder and salt.
Add the flour and milk alternately, beginning and ending with the flour. Stir in the vanilla.
Spoon the batter over the pineapple in the cake pan or skillet, and place the pan in the oven. Bake until the cake tests done (in about 40 minutes).
Let the cake stand for 10 minutes; then invert it onto a serving plate. You may need help with this if you use the cast-iron skillet as it feels a bit heavy during the inverting process.
This cake is best served slightly warm with or without a little whipped cream.
Serves 6 to 8.

Colonial Williamsburg created this lovely pineapple wreath.

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12 Responses to “Upside Down”

  1. Donna says:

    This is one of my favorite desserts of all time. Yes, it’s the sticky sweet pineapple cnd cherries that I love from my childhood. Since we had an electric stove in the house I grew up in, my Mom would heat the butter and brown sugar in the cake pan, on the burner. She did not make this often, it was a special treat. I think I’ve made it once or twice in my 8×8 square glass pan. I have a sinking feeling this may be my weekend project…

    Now, have you got a good recipe for a Boston Cream Pie? That was my absolute favorite dessert as a kid. It fostered my love for anything with custard to this day. Eclairs, creme brulee, a custard doughnut, the list goes on. I need your help as I want to make and conquer the art of making pastry cream, it will be the death of me, I am certain. That and sausage and bacon.

  2. tinkyweisblat says:

    Here you go, Donna. It was a little flat (maybe I didn’t have the eggs at room temperature?) but very tasty.
    I hope it isn’t REALLY the death of you!

  3. That looks wonderful! I’ve only made pineapple upside down cake once because I never grew up eating it but it was delicious, (I added some extra sharp cheddar cheese to my batter) So thanks for the reminder…I’ll be making this again soon-Thanks!

  4. Grad says:

    I lived in Hawaii for about 4 years as a young bride, and the pineapples were heaven! Even though most of them come from Hawaii still, they don’t seem to taste the same when eaten in Georgia. Maybe pineapple is a state of mind. But, pineapple upside down cake is one of the cakes I could actually sell to my kids. They used to eat the top (bottom) part and leave the cake part, though. Yours looks super (and so does the cake plate).

  5. I think we have these sort of food days/weeks here, but I’ve never heard of pineapple upside down cake day!!

  6. A friend gave us a fresh pineapple from his garden last week – wish I’d seen this then! But I’m sure we’ll get more and will look forward to pineapple upside down cake.

  7. flaneur says:

    As a kid my favorite cake was undoubtedly my mother’s chocolate cake. But in retrospect, faulty memory, or an evolving taste, my favorite cake has got to be pineapple upside down cake. I quite agree that the question of fresh versus canned pineapple is rendered moot after the cake is baked, but the virtue of labor-saving canned pineapple are the rings, which when arranged delicately produce a wonderful stained-glass effect (with cherries at the center hole of each pineapple ring). I have a 22″ diameter paella pan (don’t ask why) and I can imagine, given enough colorful fruit and relying on some of the citron used in fruit cakes, creating a huge upside down cake with the luminosity of the rose window at Chartres cathedral. On the other hand there is the technical problem of upside downing a cake that large.

    There is only one way in which a pineapple upside down cake can disappoint: when too little brown sugar is used and that marvelous, emphatic caramelized taste (which brings out the glory of the baked pineapple) is insufficient, one cannot help feeling something is missing. As with stained glass, the glass (fruit) is important but so is the lead (brown sugar) that solders the pieces and seals the deal. In future years (next year) it will become traditional and de rigueur to send friends a pineapple upside down cake. The cake may not travel well in the hands of UPS (not our delivery guy at any rate) but the taste will be divine. I should give you my mailing address…

  8. Laurie says:

    Hi Tinky! I love pineapple upside down cake by my favorite cake is tres leches. Thinking about making it for an upcoming Cinco De Mayo party!

  9. Sue Haas says:

    Yes, a well-loved special cake for company at my mother’s in Michigan in the ’50s and ’60s. I remember canned pineapple rings with half of a maraschino cherry plopped in the center of each ring. My mother also made rhubarb upside down cake with fresh rhubarb–also yummy. Let me know if you’d like the recipe. At the Trophy Cupcake shop in Seattle I recently saw their “Pineapple Upside Down Cake” cupcake–complete with a cherry on top. Fun!

  10. andrea says:

    OK… if we’re gonna be friends, I’d better keep my gym membership up-to-date. I gained 5 pounds just reading the recipe — but it was totally worth it.

  11. Charles "Buckey" Grimm says:

    It has been ages since I have had Pineapple Upside Down Cake, The recipe sounds so great. It is now officially on this weekend’s menu.

  12. tinkyweisblat says:

    Thanks, all, for the enthusiasm. Flaneur, I wish I could send you a cake! Abigail, I’m jealous of you, living as you do near “real” pineapple. Sue—yes, yes! Andrea, thanks for leaving my 1000th comment. And Laurie, I also love tres leches. You’re giving me some Cinco de Mayo inspiration, too……

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