American Cakes – Pineapple Upside-Down Cake

Pineapple Upside Down Cake on The History Kitchen #vintage #recipe

Pineapple upside-down cake is a single layer basic yellow butter cake inverted after baking to reveal a glistening mosaic of caramelized canned pineapple. Any frosting or additional gilding is unwarranted. A variation of this treat was upside-down pudding, consisting of a Victoria sponge cake inverted after baking to reveal a decorative fruit layer.

Cooking a cake or tart with a fruit layer on the bottom and afterwards inverting it is neither new nor indigenous to America. Among the most famous of these treats is the French tarte tatin, an early 20th century upside-down apple tart. Around that time, Mrs. Allen’s Cook Book by Ida Allen (Boston, 1917) contained four upside-down pies, such as “Upside-Down Apple Pie.” Central Europeans have long enjoyed schmarren by cooking apple slices in a skillet, adding a pancake batter, then inverting it to reveal the apples on top. In a similar manner, the English prepared various skillet custards and puddings called a tansy, the name derived from a European bitter herb that was initially added as a flavoring. Tansy in colonial America, absent the herb, was made by cooking sliced tart apple rounds in a skillet, adding beaten eggs flavored with sugar, rosewater, and nutmeg, cooking it until set, then inverting it onto a plate.

In the 19th century, Americans without access to an oven made cornbreads, biscuits, and shortcakes over the coals of a fire in a spider (a cast-iron skillet with legs – more common than a plain skillet through much of the 19th century), which by the mid-1800s became known as spider cakes. These were frequently served warm for breakfast. As the home iron oven became increasingly commonplace in the country, flat-bottomed frying pans supplanted the spider and the term skillet cake emerged. In addition, Americans began baking chemically-leavened butter cakes in the skillets. To enhance the simple cake, huckleberries might be stirred into the batter or various fruits mixed with a sugar-and-butter syrup before adding the batter to the pan. Blackened cast-iron skillets proved ideal for caramelizing the sugar, while preventing the butter from burning. The June/July 1925 issue (Vol. XXX, No 1) of “American Cookery,” formerly “The Boston Cooking-School Magazine,” noted: “A heavy iron frying pan, from eight to ten inches in diameter, is recommended, and some of our friends make the cake in an earthen baking dish.”

In the early 1920s, a synonym emerged for skillet cakes with a caramelized fruit bottom – upside-down cake. The June/July 1925 issue of “American Cookery,” which suggested both pineapple and prunes as the fruit, explained: “This cake is variously named Pineapple Cake, Pineapple or Apricot Torte, Caramel Pudding, Frying Pan Cake, Skillet Cake, Griddle Cake, Pineapple Glace, Different Pudding, Chesterfield Pie; but Skillet or Upside-Down Cake are the commonest names.” The earliest record of the term “Upside-Down Cake” appeared in 1923 in several sources, including the March 15, 1923 issue of the Syracuse Herald (p. 15), in a column entitled “Unusual Prune Dishes,” which, as the designation connotes, provided a version made with dried plums (and no mention of pineapple). At this early point, the recipe already featured a common element of classic upside-down cakes — fruit arranged atop a brown sugar syrup in an iron skillet:

Upside-Down Cake.

Wash and soak the prunes in warm water for several hours; drain and remove pits; beat one egg till light, gradually add one-half cup of sugar; beat until creamy. Measure one cup sifted flour, sift again with one teaspoon baking powder; add to the egg mixture alternately with one quarter cup milk or water, beat well; add two tablespoons melted shortening, one teaspoon vanilla. Melt two tablespoons butter in a small iron frying pan: spread one half cup brown sugar evenly over pan, then one quarter cup chopped walnuts; cover with prunes, then pour on cake batter. Bake in a moderate oven about 25 minutes. Will serve five persons.

Pineapple Upside Down Cake on The History Kitchen #vintage #recipe

Besides dried plums and traditional apple slices, cooks early on experimented with various fruits in upside-down cake, generally tart ones to balance the sweet syrup. The “Upside Down Cake” in the September 11, 1926 issue of the Port Arthur News (TX) used pitted sour cherries. Canned apricot halves were another early favorite. However, the paradigmatic upside-down cake appeared when around 1923 someone substituted canned pineapple slices. No one knows the identity of the first person to use pineapple in this cake or where this occurred. Canned pineapple initially became commonplace on the American mainland after World War I and was still an exotic item in the 1920s. The earliest recipe for the pineapple variation may have been in A Book of Practical Recipes by the Chicago Evening American, which unfortunately lacks a copyright date (the newspaper was published from 1914-1939) but the accepted date among book collectors is 1923.

Pineapple Upside Down Cake

¼ pound butter
1 medium can pineapple
1 cup brown sugar

Melt butter slightly in heavy frying pan. Spread over this the brown sugar and then lay on pineapple.

(Batter)

3 eggs
1 cup flour
1 cup sugar
1 teaspoon baking powder
5 tablespoons pineapple juice

Beat egg yolks, add sugar, pineapple juice, flour sifted with baking powder. Fold in beaten egg whites. Pour over first mixture and bake in moderate oven. When done place cake plate on top of pan and reverse. Serve with whipped cream. (Pan should be eleven inches in diameter — and three inches deep.)

A Book of Practical Recipes also included a similar recipe employing the venerable term — “Caramel Pineapple Cake (Skillet Cake)”:

Caramel Pineapple Cake (Skillet Cake)

Put three tablespoonsful of butter and a cupful of brown sugar in an iron frying pan. Let it simmer for a few minutes. Then add sliced canned pineapple just to fit pan. A medium pan requires about seven slices around and one in the middle. Then make a batter of three eggs, one and a half cups of sugar, one-half cup water, one teaspoon vanilla, a pinch of salt, one and a half teaspoons baking powder, one and a half cups flour.

The pineapple concept, under various names, quickly spread nationwide. The August 1924 issue of Dietary Administration and Therapy (Cleveland, OH) provided a recipe for “Pineapple Upside Down Cake.” A cake under the title “Pineapple Glacé” was included in a 1924 community cookbook from Seattle. The cookbook of the Home Extension Clubs of Miami County (1926) contained a “Pineapple Skillet Cake.” In November 1925, a Gold Medal Flour magazine ad replete with four-color picture featured a recipe for “Pineapple Upside-Down Cake” with candied cherries, which further popularized the dish. Early on, many cooks placed pecans or walnuts in the crevices of the pineapple slices and maraschino cherries in the pineapple holes. When Dole held a pineapple recipe contest in 1926, among the 60,000 entries submitted were 2,500 for pineapple upside-down cake; at the time, still an exciting new dish. The 1931 edition of Aunt Sammy’s Radio Recipes (Uncle Sam’s wife) published by the U.S. Department of Agriculture (taken from a five-day a week 15-minute radio show) widely disseminated a printed version of the “Pineapple Upside-Down Cake” (and also “Apple Upside-Down Cake”).

By the mid-1930s, pineapple upside-down cake was one of, if not the most widely made cake in American homes. It was not only a comfort food and bake sale and potluck church social standard, but also dessert for holidays and other festive occasions. Red and green cherries rendered it a Christmas treat. As Americans increasingly purchased standardized baking utensils and lost interest in cast-iron skillets, upside-down cakes shifted primarily to round and square baking pans and the name “skillet cake” all but disappeared. The 1950s and 60s were perhaps the heyday of this cake (frequently made with boxed cake mix), as it became a pop icon. In the 1970s, as American culture and tastes changed, some began viewing upside-down cake as something of a cliché and out-of-style. Nevertheless, many home cooks continue to rely on this retro treat for a tasty dessert. April 20th became National Pineapple Upside-Down Cake Day.

THK Note: If you’d like a more natural (and historical!) alternative to maraschino cherries, check out Martha Washington’s Preserved Cherries. They won’t look as pretty (or retro) as the bright pink maraschino cherries, but the flavor will be quite nice.

Food Photography and Styling by Louise Mellor

Pineapple Upside Down Cake on The History Kitchen #vintage #recipe

Pineapple Upside-Down Cake

Topping Ingredients

  • ¼ cup unsalted butter, melted (½ stick/2 ounces/60 grams)
  • ¾ cup packed light brown sugar, or ½ cup light brown sugar and ¼ cup dark brown sugar (5.75 ounces/170 grams)
  • 6 to 9 pineapple slices (½-inch thick), drained (12 to 20 ounces/340 to 570 grams), or about 2½ cups crushed pineapple, drained (20 ounces/560 grams)
  • 8 to 12 maraschino cherries (optional)
  • ¼ cup pecan or walnut halves (optional) (1 ounce/30 grams)

Batter Ingredients

  • 1¾ cups all-purpose flour, sifted, or ¾ cup all-purpose flour and ¾ cup cake flour (7.5 ounces/210 grams)
  • 1½ teaspoons double-acting baking powder
  • ½ teaspoon salt
  • ½ teaspoon ground cinnamon, ¼ teaspoon ground mace or nutmeg, or 2 teaspoons ground cardamom or ginger (optional)
  • ½ cup unsalted butter or 1/3 cup vegetable shortening, softened (65 to 67°F) (1 stick/4 ounces/115 grams)
  • ¾ cup granulated sugar (5.25 ounces/150 grams)
  • 2 large eggs (6 tablespoons/3.5 ounces/100 grams)
  • 1½ teaspoons vanilla extract or 1 teaspoon vanilla and ¾ teaspoon grated lemon extract, ½ teaspoon almond extract, 1/8 teaspoon coconut flavor, or 1 tablespoon dark rum (optional)
  • ½ cup pineapple juice or milk (4.25 ounces/120 grams)
Total Time: 1 Hour 15 Minutes
Servings: 8 to 10 servings - One 10-inch round or 9-inch square cake
  • Position a rack in the lower third of the oven. Preheat the oven to 350°F (325°F for a convection oven).

To make the topping:

  • In a 9- to 10-inch ovenproof skillet (it will produce flared sides), 10-inch round baking pan (for straight sides), or 9-inch square baking pan, stir in the butter and sugar, then spread the mixture evenly over the pan.
  • Pineapple Upside Down Cake on The History Kitchen #vintage #recipeArrange one pineapple slice in the center of the pan and the remaining slices around it. You can break some of the slices to fill in the gaps in the outer portion. If using, place the cherries and/or pecan halves (flat side up) in the centers and around the pineapple.
  • Pineapple Upside Down Cake on The History Kitchen #vintage #recipe

To make the batter:

  • Sift together the flour, baking powder, salt, and, if using, cinnamon.
  • Pineapple Upside Down Cake on The History Kitchen #vintage #recipeIn a large bowl, beat the butter on low speed until smooth, about 2 minutes. Increase the speed to medium, gradually add the sugar, and beat until light and fluffy, about 4 minutes.
  • Pineapple Upside Down Cake on The History Kitchen #vintage #recipeBeat in the eggs, one at a time.
  • Pineapple Upside Down Cake on The History Kitchen #vintage #recipeAdd the vanilla and, if using, lemon extract (or other flavoring extracts/rum). Add the flour mixture alternately with the juice (4 portions for the flour; 3 portions for the juice) beginning and ending with the flour, and beat until creamy, about 1 minute.
  • Pineapple Upside Down Cake on The History Kitchen #vintage #recipePour the batter over the pineapple.
  • Pineapple Upside Down Cake on The History Kitchen #vintage #recipeBake until a tester inserted in the center comes out clean and the cake springs back when lightly touched or the cake reaches an internal temperature of 190°F on an instant-read thermometer, 45 to 55 minutes.
  • Let the cake cool in the pan set on a wire rack for 10 minutes, then run a knife around the edge, invert onto a serving plate, and lift off the pan. Serve slightly warm or at room temperature. Wrap in plastic wrap and store at room temperature for up to 2 days or in the freezer for up to 2 months.
  • Pineapple Upside Down Cake on The History Kitchen #vintage #recipe
  • VARIATIONS:
  • Buttermilk Upside-Down Cake: Substitute ½ cup buttermilk or sour cream for the pineapple juice, reduce the baking powder to 1 teaspoon, and add ¼ teaspoon baking soda.
  • Oil Upside-Down Cake: Substitute 1/3 cup vegetable oil for the butter, increase the pineapple juice or milk to ¾ cup, and add ½ teaspoon baking soda.
  • Pina Colada Upside-Down Cake: Substitute 2/3 cup unsweetened coconut milk for the juice and add ¾ teaspoon rum extract and 1/3 cup (1 ounce/30 grams) flaked coconut.
  • Although pineapple is the most common fruit used in upside-down cakes, many other types, fresh or canned, make tasty and interesting substitutes, including 3 to 4 (1 pound/455 grams) peeled, cored, and thinly sliced cooking apples, 1½ cups (8.25 ounces/240 grams) drained canned apricot halves, 3 medium (total 1 pound/455 grams) bananas cut into ¼-inch-thick slices, 1½ to 2 cups blueberries, 2 cups (10.5 ounces/300 grams) pitted cherries, 2 cups (7 ounces/200 grams) cranberries, 3 to 4 medium (1 pound/455 grams) peeled, halved, and pitted peaches or nectarines, or 8 (1 pound/455 grams) pitted and thickly sliced plums.

About Gil Marks

Gil Marks writes about the history of American Cakes for The History Kitchen, revealing the history and culture of the United States through its classic treat. Gil is a leading authority on the history and culture of culinary subjects, as well as a James Beard Award-winning author, historian, chef and social worker. Read more...
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Category: Baked Goods, Brunch, Desserts, Kosher - Dairy, Recipes, Slide Show, Vegetarian, Vintage Recipes

Comments (46)Post a Comment

  1. Oh my Mother used to make this when we were kids! Beautiful! Thanks for the reminder. Think I will try it out soon on the grandkids! :)

  2. Bonnie Emm says:

    ´Just made one–with gluten free flour–yesterday, using a classic recipe from a 1940´s cookbook that´s been in my family for years. The only change I´ve made recently is to skip the rings and use a whole can of drained pineapple chunks instead. I´m thinking of upping the butter and brown sugar, too, since there´s never enough of that.

    • Tori Avey says:

      Bonnie did you sub the GF flour cup-for-cup? What is your favorite GF flour substitute? I’m sure other gluten free readers would love to hear!

  3. Wow that looks pretty !

  4. My mom always used to make this in her frying pan :-) Brings back wonderful memories!!

  5. Takes me back in time….Mama and Grandma both made using cast iron skillet.yep!

  6. Thanks for always sharing the history behind the recipes.

  7. This is one of my favorite cakes. It has to be baked in a well seasoned cast iron frying pan or simply does not get baked properly.

  8. You can call when you make it and share it with your sister too. I used to make it years ago too! It´s so good! I remember we thought it was such a treat when Mom made it.

  9. Great article and great looking cake! I have my mother´s handwritten recipe still. Makes me want to make it soon. :-)

  10. synchronicity. i just put an apricot one in the oven.

  11. Oh, i want to try pina variety coconut and pinapple! Darn, i just went to the store! I know i am prolly missing some ingredients! You always inspire me to bake! So cool out now bake sales would flurish!

  12. Jan Klein says:

    My father´s all time favorite!

  13. I got custody of Mom´s skillet and will leave it to the kid who knows not to put it in the dishwasher. It was made to use on a wood stove.

  14. I love reading your blog and posts. It is a pleasant mixture of both of my “favs”, history and cooking. Thank you!!

  15. This looks exactly like the one my Mum used to make in the 1960s

  16. jujubees says:

    Is there a gluten free version of this?

    • Tori Avey says:

      Hi Jujubees… a gluten free version was not included in this post, however you could try subbing a gluten free baking mix for the flour such as King Arthur Gluten Free Multipurpose Flour: link to theshiksa.com I’ve had good luck subbing it cup-for-cup in simple cake recipes like this one, however I haven’t tried this particular cake, so I can’t promise it will work. If you try it, let us know how it works for you!

  17. Harriet says:

    The last upside down cake I made, several weeks ago, was for a Family Friday Shabbat dinner, at the synagogue where I am one of the cooks in the kitchen. I had some pears that needed to be used, I had a recipe for a simmering brown sugar, butter, and maple syrup going into the cast iron skillet, before the fruit, carmelizing the fruit, adding the cake topping and baking. I cut back on the amount of butter, brown sugar, and maple syrup, as I did not want to make it too sweet.

    There was nothing left… I believe our new Rabbi’s spouse ate most of it, as he raved about it…

  18. Sonny Jaben says:

    Oh. Emm. Gee. My mother used to make that. My alltime favorite.

  19. Cheryl says:

    I make this every other Thanksgiving…perfect fall dish. ONLY…I go to Joann Fabrics and purchase some silk leaves and put them around the cake. Even more Fall color plus LUCIOUS!!

  20. Jennifer Onaits Legler says:

    My Mom made this often. Don’t recall her having a cast iron skillet. She just used a regular cake pan. Yummy.

  21. I remember being told that the cake was actually a mistake…!!! Sometimes those are the best kind… <3

  22. I remember baking this with my mother…

  23. So glad that you started this blog. Learning about different cultures and history is one of the things that initially drew me towards expanding my cooking!!!

  24. Yummy I have made quite a few of these !!!!!

  25. this is my most favorite cake to make..

  26. Jenny Busch says:

    Great teaseing cake, it runs even with devils food cakes in my opinion. Again that what Momma and Grandmother made, along with her Strawberry chiffon pie. Oh dear, now I’ve made my self hungry! JB

  27. Barry Scott says:

    Wow, does that bring back memories. Can’t wait to try it.

  28. one of my favorites…:)

  29. Faigi says:

    B”H

    Streamline the work by mixing some butter and brown sugar in a plate, and placing it in chunks on the bottom of the baking pan randomly. It will melt during baking and form that beautiful and yummy glaze.

  30. strange I just downloaded a recipe on Friday…it is really delicious and simple to make…great dessert!!

  31. Lisa stark says:

    But how do you make it with a sponge cake batter made with 13 eggs and no flour? When it rises how do you turn it over???

  32. My mother used to make this and I never got her recipe. So glad I found it on The History Kitchen page!

  33. Mibi Astron says:

    Wow! I haven’t thought if this cake ages. I learned how to make it in Home Economic’s class. (Mom wasn’t much of a baker). I think I’ll make it for the niece. Thanks for the memory.

  34. Kathi Montoya says:

    My absolute favorite cake, hands down…It is the only ritualized bit of cookery I do. I drain the pineapple slices, on a bed of thick paper towels, then blot them until they are bone-dry. I make the sugar and butter mix, always adding just a tiny bit more than called for in the recipe. The pineapple slices are cut in half, so they nestle into into each other and form half-moon patterns.I do NOT add the cherries, until the cake is un-molded. Then cherries are added…the crusty brown bits, the glistening fruit half-rings, the frankly artificial vivid red of the cherries…love other cakes, but not one can equal this…

  35. Esti says:

    Excited about the gluten free options for this recipe, great idea for Rosh Hashana!

  36. My mother made this in a cast iron skillet on top of thestove – best smell on earth coming home from school in the cold weather!!1

  37. Absolutely the best cake on earth. :-)

  38. Bridget Connors says:

    I just came across this recipe & had to share this story. My mom’s home ec class in high school had to make this cake. Everyone was partnered & they all had to do each step together at the same time. Well, the cakes were made, cooled enough to turn the cakes out, and when they did, everyone’s cake had pineapple on top except my mom’s! The sister teaching the class asked my mom if she put the pineapple in the pan or did she eat the pineapple, my mom swore she didn’t, her cooking partner swore mom didn’t (Mom’s partner was already sworn to become a nun, so the sister believed her). When they cut the cake, the slices were EXACTLY in the middle of the cake! Mom said nobody in the class (including the sister teaching) had ever heard or seen that happen to a pineapple upside-down cake, and it never happened to Mom again!

  39. Tammy Perkins says:

    My husband LOVES pineapple upside down cake. I make it for his birthday every year. This year, after enjoying the cake, my husband asked if I could make it next time with a brown sugar glaze in the middle of it (along with the brown sugar pineapple on top). He wants the sweetness swirled in middle like a coffee cake might have. I am not sure how to do this, or if it can even be done. I have searched the internet but haven’t found a variation that does that. Do you have any idea how I could accomplish this challenge? Thank you for any help you can provide :)

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