Pineapple Upside Down Cheesecake – Best Recipe

Pineapple Upside Down Cheesecake – Best Recipe

Eva 28 mayo, 2023
Este post también está disponible en Spanish

For a couple of years I had the idea of sharing with you retro or vintage recipes. A sort of “saga” that would gather some recipes with origins between the years 1920-1960. Those of you who have been reading me for a long time, know that I have a special devotion for this kind of recipes and style. I don’t know if what attracts me so much is the mix of somewhat tacky, but elegant compositions. With that touch that wants to show the interest to surprise our family and friends, but at the same time that abuses a little of an excess of decoration. I think they have a certain charm. I like them a lot. The thing is that, finally, after gathering some recipes I am going to share with you this little recipe book with recipes from this time of the year.

The first recipe of this compilation is this Pineapple Upside Down Cheesecake – Best Recipe. Famous pineapple upside down cake, but also accompanied by a cheesecake base. The original recipe consists only of the inverted pineapple sponge cake. But when I found this recipe combining both elements… I couldn’t resist. Who can say no to a good cheesecake?

My initial idea was just to make the pineapple upside down cake. A simple recipe to carry out and that we will have ready in a few minutes. But then this wonderful recipe with the cheesecake base appeared… Impossible to turn a blind eye to something like that. So in the end I thought, ok I need them, and I made the recipe with both elaborations.

In your case, if you wish, you don’t have to prepare both. You can make just the Pineapple Upside Down Cake, or even prepare the cheesecake and omit the cake. Of course, I warn you in advance that the combination of the two recipes in the same dish is awesome.

Pineapple Upside Down Cheesecake - Best Recipe

Upside Down Cakes.

According to most historians, it was at the end of the 19th century when the term “upside down cake” began to appear. Until that time, this type of cake was known under the term “skillet cakes“.

The reason for this is that, until that time, ovens were not always accessible, skillet cakes were born out of practicality. They were made in the popular cast-iron skillets on top of stoves. The first inverted cakes were made with seasonal fruits such as apples and cherries; canned pineapple had not yet been invented.

A recipe of French origin, similar to this preparation, was the Apple Tarte Tatin, created in the 1880s. On my website you also have this option with quinces, this one with peaches and this one with strawberries and rhubarb.

According to Gil Marks, who wrote about pineapple cake for Tori Avey, the first known use of the term “upside-down cake” was in 1923, for a cake made with dried plums (about 10 years ago, Oh my God!, I left you this Plum Marzipan Upside Down Cake and this one made with blood oranges).

It is likely that the name derived from “upside-down pies”, which appeared in the previous decade.

Pineapple, a luxury not available to everyone.

George Washington wrote that of all fruits, he liked none so much as the pineapple. He first encountered this fruit in Barbados and later bought it whenever possible from the ship captains who traded their wares bringing them from the West Indies. He was one of the lucky few to enjoy this fruit.

It was a very expensive fruit at the time, so much so that some hostesses would rent the fruit from bakers to display as a centerpiece, and then return it uneaten. The pineapple was rented again and again, until it rotted. I find this fact unbelievable… One more proof of how little we value everything we have within our reach today. We are privileged and we are not aware of it.

In British and American cookbooks of the 18th and 19th centuries, recipes with pineapple occasionally appear. But most of them were just instructions for cutting and serving the fruit raw, or for preserving it. As the 19th century progressed, more pineapples were imported from Florida, the Caribbean and Central America, with a consequent increase in recipes for using them. Most were recipes for preserves, compotes and cold dishes such as pineapple salad, ice cream and Bavarian cream.

The manufacture of canned pineapple did not begin until 1901, when Jim Dole founded the Hawaiian Pineapple Company (actually Dole Company) and began producing and marketing massive quantities of canned pineapple.

Pineapples had been grown in Hawaii since the early 1800s, and there were canneries as early as the 1880s, but none on the scale of Dole’s. It had a machine capable of peeling, coring and cutting 100 pineapples per minute. Soon, he and other Hawaiian producers were producing so much pineapple that they needed an advertising campaign to convince Americans to buy it all.

Pineapple Upside Down Cheesecake - Best Recipe

Pineapple Upside Down Cake origin.

In 1925, the Hawaiian Pineapple Company sponsored a pineapple recipe contest in which judges from Fannie Farmer’s School, Good Housekeeping and McCall’s Magazine participated. Reportedly, 2,500 of the 60,000 entries were pineapple upside down cake recipes. The company decided to run an announcement about the flood of pineapple upside-down cake recipes it received, leading to the incredible popularity of this recipe.

The winner was a pineapple upside-down cake from Mrs. Robert Davis of Norfolk, Virginia. Dole widely promoted Mrs. Davis’ winning recipe, and soon the pineapple upside-down cake became one of the most popular cakes in North America.

Pineapple upside-down cakes began appearing in magazines, cookbooks and advertisements. In 1927, a booklet entitled Aunt Sammy’s Radio Recipes was published by the U.S. Department of Agriculture’s Bureau of Home Economics and written by Ruth Van Deman and Fanny Walker Yeatman. The booklet was a compilation of 70 menus and some 300 recipes broadcast between October 1926 and June 1927 on the radio service’s “Housekeepers’ Chat” programs.

The first two printings of this recipe were found in a 1924 Seattle charity cookbook under the name Pineapple Glacé and, in a 1925 women’s magazine, there was a full-page ad for Gold Medal flour.

Maraschino cherries had become very popular in the United States in the early 20th century, which may explain why they were chosen as a garnish for this tart. It is likely that artificially dyed cherries were used in the cakes of the 1920s.

During the 1930s, the pie was considered less elegant, but was no less popular. A 1934 article stated that “no woman can really consider herself a finished amateur pastry chef until she has at some point in her career baked an upside-down cake.” In the 1930s, there were many recipes that made the cake with other fruits such as peach and apricot. Also in the 1930s, Omega flour ran an ad in which it gave away an upside-down cake pan to anyone who bought a 10-pound sack of flour.

Pineapple Upside Down Cheesecake - Best Recipe

What ingredients are in Pineapple Upside Down Cake?

This is a really simple cake to make. It consists of pouring a sponge cake batter over pineapple slices that rest on a base of brown sugar and butter, with which we can make a kind of caramel. It is usually made in a frying pan or skillet, although nowadays we can make it in a baking pan. Sometimes pecans and maraschino or candied cherries are added. Although the latter are very common since they add a touch of color.

It is then baked and, finally, it is turned upside down on a dish so that the bottom becomes the top. Hence its name “upside down” or “inverted”.

But… Let’s give it a little twist. In addition to preparing this wonderful Pineapple Upside Down Cake, we will prepare a soft and delicate cheesecake to be placed on the bottom, as a base. The texture of this cheesecake is very reminiscent of a mousse. The cheese flavor is intense… Each spoonful melts in the mouth. A real delight.

Of course, the base of the cheesecake could not be other than the famous base of crushed cookies and butter.

As much as I have searched, I have not been able to find the origin of this incredible combination; cheesecake and pineapple upside down cake. I’ve seen many recipes and even a recipe from The Cheesecake Factory, but it doesn’t detail who the creator was. So if any of you know him, I’ll be happy to read it so I can update the post!

Recipe Pineapple Upside Down Cheesecake - Best Recipe



  • 230 g cookies
  • 110 g unsalted butter


  • 1375 g cheese cream
  • 315 g sugar
  • 125 g heavy cream
  • 5 large eggs
  • 4 large egg yolks
  • 3 tsp natural vanilla extract



  • 120 g muscovado sugar or panela
  • 65 g unsalted butter
  • pineapple slices in juice
  • candied cherries or Marraschino cherries
  • pecans

Pineapple sponge cake:

  • 280 g cake flour
  • 125 g unsalted butter, room temperature
  • 70 g heavy cream
  • 85 g whole milk
  • 2 large eggs
  • 9 g baking powder
  • 3 g salt


*In these products you have a 5% discount on the website Claudia&Julia using this code BAKESTREET. Delivers throughout Europe.



Prepare crust.
  1. Place the cookies in a food processor and grind until completely pulverized. If desired, we can put the cookies in a zip bag and crush them with a rolling pin.
  2. Transfer crushed cookies into a bowl and pour the melted butter. Mix until completely homogenized.
Prepare the mold.
  1. Line a square baking pan with baking paper, grease the entire inner surface with butter or release spray.
  2. Place the cookie mixture on the base of the mold. Smooth the surface with the help of a spoon or a small rolling pin.
  3. Bake at 345ºF/175ºC for 8 minutes.
  4. Remove and set aside on a cooling rack.
Prepare cheesecake.
  1. Preheat oven to 345ºF/175ºC with heat up and down. Place, at half height, a wide dish with boiling water. Bake the cheesecake in a bain-marie.
  2. In the bowl of the KitchenAid, add the cream cheese, sugar and vanilla. Mix with the whisk to soften the texture.
  3. Begin to add the eggs, one at a time and wait until they are fully integrated before adding the next one. Whenever necessary, stop the mixer and lower the cream from the sides with the help of a silicone spatula.
  4. Once the eggs have been incorporated, add the yolks. We will do it in two batches and wait until they are completely integrated before adding the next one.
  5. Finally, add the cream and mix until homogenized.
  6. Pour the mixture into the mold, on the cookie base, and bake in a bain-marie for 1 hour and 20-30 minutes. We will look at the central part of the cheesecake, it should not be sunken, but straight. When moving the mold, the cheesecake will be "dancing", we will see that it has a swaying. When the last 20 minutes of cooking time are left, reduce the temperature to 320ºF/160ºC and remove the upper heat.
  7. After the baking time, turn off the oven and with the door closed, let the cheesecake stand inside for 1 hour.
  8. Remove from the oven, without unmolding, let it cool completely on a wire rack.
  9. Cover the surface with plastic wrap and refrigerate until the next day.
    Pineapple Upside Down Cheesecake - Best Recipe


  1. Unmold the cheesecake. My initial intention was to remove it with the strips of baking paper that I prepared in the mold... But it didn't work. To unmold this cheesecake in a fixed and not removable mold, we will have to turn the cheesecake over a wide plate and turn it again to place it in the correct position.
  2. It is important to use Teflon squares or baking paper when flipping the cheesecake to avoid damaging the surface. In the video I show you how to do it.
Prepare the topping for the pineapple cake.
  1. We will use the same mold in which we prepared the cheesecake. Wash it well and line the inside with baking paper except for the base. This will only be greased with butter.
  2. In a saucepan add the butter, 65 g, and sugar, 120 g, of the topping. Place over medium-low heat and allow to melt completely.
  3. Next, pour this "caramel" inside the mold and spread it so that it covers the entire base of the mold.
  4. Decorate the base with pineapple slices, candied cherries and pecans. In my case I have left a suggestion of presentation, but you can carry out the one you like best or that fits the shape of your mold (round, square or rectangular).
  5. Set aside.
    Pineapple Upside Down Cheesecake - Best Recipe
Prepare the sponge cake.
  1. In the bowl of the KitchenAid add the butter and sugar. Mix with the whisk until a slightly creamy texture is achieved.
  2. Begin to add the eggs, one at a time and wait until they are fully integrated before adding the next one.
  3. Mix the flour together with the baking powder and salt, set aside.
    Change the whisk for the flat beater and proceed to incorporate, alternately, the dry and liquid ingredients. Add a little of the flour mixture, while mixing at the lowest speed, alternating with the milk, vanilla and cream.
  4. Mix only until no flour remains, be careful not to over mix the cake batter.
Pour in the mold and bake.
  1. Pour the batter into the reserved mold and over the fruit. Smooth the surface.
  2. Bake in a medium oven at 345ºF/175ºC with heat up and down for 35-40 minutes. Before taking it out, check that the cake is ready. To do this, prick with a toothpick in the central part of the cake, it should come out clean or with no remains of batter stuck to it.
  3. Remove from the oven, let stand 2 minutes in the mold and proceed to unmold. We must turn it over, in the same way we did with the cheesecake.
  4. Place on a large plate and, being careful not to burn ourselves, turn it over.
  5. We can let it warm or cool before placing it on top of the cheesecake, as we prefer.
Assemble Pineapple Upside Down Cheesecake.
  1. The last step is to place the pineapple cake on the cheesecake. To do this we can use a baker's shovel (like the ones for pizza) or a large pastry spatula.
  2. We will place the pineapple sponge cake on the cheesecake, very carefully, and trying to adjust it as best as possible.
  3. NOTE: If there is a wide gap between the sponge cake and the pineapple slices on the surface, once baked, we can fill those gaps with pecan nuts cut lengthwise.
  4. Serve.
    Pineapple Upside Down Cheesecake - Best Recipe


  • For the crust of the cheesecake we can use the variety of cookies we want. In my case I use some similar to Digestive cookies because I like their flavor, but we can choose the ones we like or prefer.
  • It is important to use a good cream cheese because the flavor of the cheesecake will be conditioned by this ingredient. We use a lot of it.
  • My square mold is this one. It is ideal for elaborations that are baked in a bain-marie, besides it is very easy to unmold if you follow the steps that I detail.
  • It is very important to bake the cheesecake in a bain-marie to make it moist and prevent the surface from cracking or splitting.
  • We will know that the cheesecake is ready when the entire surface is straight. You will notice that as we bake it, the central part will be slightly sunken and it will acquire volume as it bakes. We must not exceed the baking time to prevent it from being dry.
  • We should not omit the final rest of the cheesecake in the oven with the door closed to help it gradually lose temperature and prevent the surface from cracking.
  • We must let the cheesecake rest overnight in the refrigerator so that it acquires consistency, as soon as it is baked it will be extremely tender.
  • With the leftover egg whites we can prepare a Molotof, egg white pudding, macarons, Meringue Dream Cake...
  • In case your mold is like mine, it can not be disassembled, you must unmold as I show you in the video.
  • To bake the cake, we will use the same mold we used to bake the cheesecake. We need it to have the same shape.
  • In my case I lined the sides of the mold, to prevent the cake from sticking, but not the base. We will only spread a little butter on the base and then pour the caramel.
  • If desired, we can use fresh pineapple instead of canned pineapple.
  • The pineapple upside down cake is always decorated with pineapple and candied cherries. In some cases, also with pecans. I leave you a suggestion of presentation, but you can carry out the design you prefer.
  • When preparing the pineapple sponge cake, we must mix the batter only until there are no dry ingredients left. Never overmix the batter, otherwise the cake will be too dense.
  • Once the cake is baked, let it rest for a couple of minutes before unmolding it. If the cake is left to cool in the mold, the base with the fruit and caramel will stick to it.
  • Be very careful when unmolding the cake because it will be very tender. And be careful not to burn yourself.
  • Once it has cooled or lukewarm, place on the cheesecake and serve. In case of serving it warm, remember to temper the cheesecake before placing the sponge cake on it.
  • It can be kept refrigerated for 4-5 days.
    Pineapple Upside Down Cheesecake - Best Recipe

I hope you are encouraged to try this marvel, Pineapple Upside Down Cheesecake - Best Recipe, because I can tell you that it is a real marvel. It combines two elaborations that marry very well, enjoying sweet, citrus, fresh touches, without forgetting an endless number of textures. The cheesecake is... Really, it's extraordinary!

On the other hand, I've been wanting to give a twist to my videos for a while now. I'll go little by little, but I'd love to know what you think of these changes.

I wish you a wonderful Sunday!

Lots of love,

Sources:What's Cooking America, Quaint Cooking, Revolutionary Pie

Video source "Hand vintage retro radio" by Yaroslav Shuraev from Pexels

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