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My Mom's Pineapple Upside-Down Cake

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Jenny is in perpetual search for easy, weeknight recipes to attempt to feed her family. When they balk, she just eats more.

Pineapple Upside-Down Cake

Is My Mom's Pineapple Upside-Down Cake a weeknight recipe? It depends a little on how much patience you have for cooling. But is it flippin’ delicious? Well, you better run to the store and get that canned pineapple people, and don’t plan for leftovers.

I have always found it a bit curious that pineapple upside down cake has not enjoyed the culinary resurrection that so many old school desserts have luxuriated in. 

In the 20 years I lived in Manhattan, I only remember seeing it on the menu once, and as my husband pointed out last night, when we returned to Time café to get it the second time, it wasn’t even good. Ditto Los Angeles. 

I’ve never been served one at a dinner party. I don’t think I’ve even spotted a slice at the dessert station at Cleburne Cafeteria in Houston but if I did I would probably have ignored in in favor of buttermilk pie so don’t take my word for it. 

Perhaps this neglect is due to the fact that canned pineapple sort of feels synonymous with bomb shelters, or school lunches. Also, pop the cake in the Google and some of the images that come up will be uninspiring. To wit: Pineapple upside down cake, in my view, does not want to be pale in color and insipid against the fork. It does not wish for maraschino cherries hanging around in its pineapple holes. And it does not wish to have the texture of a conventional weapon. 

Instead, it wants to be dark and gooey on top, made so by a whole lot of brown sugar and butter, yet its cake part beneath somehow submissive and airy, resting under its tropical fruit life vest. It may wish to have nuts.

Having failed still to obtain a 9 inch cast iron (mine is 12 inches) I made this lovely guy in regular nine inch cake pan. The author says you must bake this in a black cast iron skillet; that is the best method no doubt but if you don’t have one you will still get a good cake out of this, I promise. 

I melted the butter in the oven as it preheated right in the cake pan, and then added my brown sugar. Next came the pineapple slices; seven fit just right as Abra Bennett promised. Don’t forget to reserve your can for the juice, as you might easily read over that step. 

After I’d gotten my dry ingredients into my beaten yolks and added that juice, I did whip my egg whites with a hand mixer, which I find faster than a KitchenAid when you’re doing low quantities. I would like to talk to you all further about the shortcomings of a standing mixer with eggs, but another day okay? 

I did not use nuts as they have few fans chez moi; they are optional but do look pretty as you can see here. 

This bakes for a while, but watch it because mine was ready to come out after 35 minutes. Yours may not be but please pay attention. 

Then, there is the cooling. Serve dinner while that is happening or you won’t be able to wait. I used a knife to loosen the sides and the cake released magically onto a plate, and I served it up while we watched “You’ve Got Mail.” As Meg Ryan’s AOL dial up sounds lit up my den, so did the ohhs and ahhs for this old time dessert. One guest said it must be the pineapple juice that makes it so feathery against the fork. This could be. I’ll have to have another slice and ponder.

My Mom's Pineapple Upside-Down Cake by Abra Bennett

Serves 8 (unless you decide to eat it all by yourself)

1/2 cup unsalted butter
1 1/2 cup firmly packed brown sugar
1 cup pecan halves
1 20 ounce can pineapple slices packed in juice, reserving 5 tablespoons juice
3 eggs, separated
1 cup sugar
1 cup all-purpose flour
1 teaspoon baking powder
1/2 teaspoon salt

See the full recipe (and save it and print it) here.

Photo by James Ransom

Tags: everyday cooking

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Comments (10)


over 3 years ago bostongal

I made this recipe and sadly found it too sweet. I will stick with the recipe in The Gourmet Cook Book (yellow cover) which is for muffins but that I bake in a cast iron pan and use fresh pineapple in. It's killer.


over 3 years ago dymnyno

You need to serve it with a dollop of unsweetened whipped cream to cut the sweetness.


over 3 years ago nancy d.

I can't wait to try it! I noticed that you mentioned Cleburne Cafeteria in Houston. It is right down the street from my house! I am a big fan and I cannot pass up the Chocolate Icebox Pie. I am going to make your cake and bring the owner a piece - who knows? - it may end up on the dessert station!!!
Thank you for sharing.


over 3 years ago mrslarkin

Mrs. Larkin is a trusted source on Baking.

Felt compelled to try this immediately, regardless of not having a skillet or a can of pineapple rings. Using cored, sliced apples, some oj, and a 9" cake pan. It's super puffy. Hoping it won't explode.


over 3 years ago drbabs

Barbara is a trusted source on General Cooking.

Oh, I wish my mother-in-law were still alive. She used to ask me to make her "pineapple pie," for which I found numerous recipes, but they never seemed to satisfy. Remembering her Yiddish tendencies to reverse words (She called her legs her feet; was a pie a cake?), I wonder if this was what she was craving. Thanks for sharing this recipe, and Happy Passover!


over 3 years ago Maudia

My husbands favorite, I have made this many times. My tip? Try fresh pineapple...sooo good.


over 3 years ago Ephany

My mom made hers with maraschino cherries in he pineapple holes. And in a skillet. I loved it so much,


over 3 years ago BoulderGalinTokyo

My dad's favorite too. Had for several birthdays.


over 3 years ago dymnyno

Thanks for the memory of my mother's cake which she always made for my birthday. True, it is seldom seen on restaurant menus . However, Bev Gannon, who has a little restaurant empire in Hawaii has it on the menu at the Haliimaile Store in Makawao. It is delicious! She makes them in an individual serving size.


over 3 years ago aargersi

Abbie is a trusted source on General Cooking.

A noble choice Jenny! I too have made this cake and heard the ooohs and ahhhhs - it is delicious! And now I want a piece. And I have no pineapple in the pantry. Rough Monday.