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The Best Pineapple Upside Down Cake…has Rum!

The Best Pineapple Upside Down Cake...has Rum!

by Creative Culinary on September 29, 2012

So I hear Pineapple Upside Down Cake is out of fashion; not popular, relegated to the annals of history as something from ‘back in the day.’ Well, guess I’m out of fashion because it’s one of my favorites. I haven’t had one in a very long time though but circumstances beyond my control made this meant to be. I received a gorgeous fruit basket from Harry and David recently and it included a perfectly fresh pineapple. I knew as soon as I saw it that I wanted to use it for this cake; a tweet I saw a few days ago about an ‘Americana’ blogging event sealed the deal.

Upside down cakes have been made for centuries in this country using cast iron skillets that were placed over a fire; the practice of putting fruit and sugar in the bottom made for a simple preparation with the topping cooking at the same time as the cake. Pineapple became a popular fruit for decorating these skillet cakes in the early 1900’s after James Dole’s engineer invented a machine to both core and cut pineapples into rings…the addition of maraschino cherries was to simply add a boost of color.

The first mention of this cake was in 1925 in a Gold Medal Flour ad that featured a full page photo of Pineapple Upside Down Cake and described it as we still know it today; a round cake with slices of pineapple, candied red cherries and a brown sugar/butter glaze.  Researchers have discovered several references through the next decade, most notably the 1936 Sears and Roebuck catalog. I’ve been making this cake for as long as I can remember and I won’t deny that for most of those years it included canned pineapple and a boxed cake mix; those conveniences are certainly what helped the cake gain notoriety during the 1960’s and 1970’s when women were leaving some of their traditional roles and demanding more ease in the kitchen.

Fast forward to today when many of us prefer to circumvent that ease and enjoy doing things ‘from scratch.’ From my experience, the extra effort is so worth it. Even peeling that pineapple was easy. I wasn’t concerned about the peeling which is really pretty easy; cut off the top and bottom and slice the outer skin off by starting at the top and and slicing downwards following the curve of the fruit. My challenge was to figure out how I would remove the core without making a mess that would ruin the whole look. To the rescue? A biscuit cutter! My biscuit cutter has a piece that is removable that make a center hole…so I removed it and used it to core each slice…yes, I was pretty doggone pleased with the results!

This recipe is so old, the card it was written on when I first decided to type it up was barely legible; I think it may have been my Grandmother Vaden’s recipe. I most often remember baking and cooking with my Grandma Bathe, my Dad’s mom, but it was true then and I’m reminded of this fact today; my Grandma Bathe was the ‘pie’ Grandma and Grandmother Vaden was the ‘cake’ Grandma. So if this was handed down from a Grandma of mine…well, Luda Vaden it must have been!

Am I am so single minded in my  thinking that I no longer offer any surprises? I guess we are all creatures of some type of habit right? So…want to guess what I added to this cake? I mean…really, how could I not? Pineapple. Brown Sugar. Butter. Don’t those just CRY out for Rum? I thought so too! I’ve updated this time honored recipe to include some dark rum…oh baby was that a good idea! The title is the truth; The Best Pineapple Upside Down Cake has Rum!

Almost a hundred years of history; my own family history of half that time; pineapples from Hawaii (thank you for joining the Union or I might be in trouble), those bright maraschino cherries…what about all that is NOT American? I hope you will dust off any notion that this is old or old fashioned. I prefer timeless or vintage; it is most definitely a cake that should not be forgotten. Come over and have a slice; you’ll see what I mean.

The Best Pineapple Upside Down Cake…has Rum!
Prep time
Cook time
Total time
Light and moist, this is the best kind of pineapple upside down cake...not too much cake!
Serves: 8 servings
For the topping:
  • ½ cup butter
  • 1 cup brown sugar
  • 1 Tbsp dark rum
  • Approximately 20 oz of sliced pineapple (use fresh or canned)
  • Maraschino cherries
  • 6-8 pecans
For the Cake:
  • 1 cup flour
  • 1 tsp baking powder
  • ⅛ teaspoon salt
  • 3 eggs, separated
  • 1 cup sugar
  • 5 Tbsp dark rum (or substitute with pineapple juice)
  • 1 teaspoon pure vanilla extract
  1. Preheat oven to 350 degrees; position a rack in the center of the oven.
  2. Add the butter to a 9-inch-round baking pan. Place the pan inside of the pre-heated oven until melted, about 5 minutes.
  3. Remove the pan from the oven and add the brown sugar and rum; stir until mixed well and even.
  4. Arrange the pineapple slices evenly in the pan; place a cherry in the center of each one and fill the center and any other open space with either additional pineapple pieces or pecans.
To make the cake:
  1. In a medium bowl, combine flour, baking powder and salt and whisk to combine.
  2. Using a stand mixer, beat the egg whites until fluffy; scrape into a clean bowl.
  3. Using the same mixing bowl, beat the egg yolks and sugar until thick and creamy; add the rum and vanilla extract and mix well..
  4. Add the flour mixture and beat until well combined.
  5. Using a spatula, fold in the egg whites until just mixed in.
  6. Pour the batter over the fruit in the cake pan and smooth to the edges.
  7. Bake for 40 minutes until the cake is golden brown and a toothpick inserted into the center comes out clean.
  8. Place on a wire rack to cool for 10 minutes.
  9. Run a knife around the edges of the pan to loosen the cake. Place a serving plate over the pan and invert carefully allowing the cake to slide out of the pan.
  10. Serve warm or at room temperature; dollop with whipping cream if desired.
This is the original recipe. To make enough for my large (12") cast iron skillet I increased each item by 50%.

The most difficult part of that? Turning that skillet over with a large plate!


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{ 51 comments… read them below or add one }

1 dalles wellman January 4, 2014 at 12:05 am

great cake! we finished it first day. I would like to make this substituting Granny Smith
apples. any suggestion on how to make them work. or a similar rum caramel recipe.
thanks for you site! it’s wonderful.


2 Creative Culinary January 4, 2014 at 11:18 am

Now I’m craving a slice myself…and I’ve got the goods on hand so this snowy day might just see it happen in a bit!

I would suggest slicing the apples thinly and proceed with all other steps as listed. The pineapple doesn’t have to really cook but your Granny Smith apples will need to soften up, so keeping those slices on the thin side should help.If looking for another change? Try using bourbon with the apples, I think that would be divine!


3 Sadie March 19, 2013 at 6:51 am

Excellent pineapple upside down cake….light, moist and not too sweet! My cake looked almost like the one pictured, with the exception of the caramel topping. Mine didn’t seep into the cake and pool around the bottom as pictured. I’m wondering if you drizzled the cake with additional caramel to serve?


4 Creative Culinary March 19, 2013 at 7:39 am

I didn’t Sadie; I just had some in the skillet and poured it on the cake. Not sure why but then I live at high altitude and sometimes things are just unexplainable here! So glad you enjoyed it; it’s probably my favorite cake.


5 Shoshanah February 12, 2013 at 6:54 pm

I just wanted to thank you for sharing this recipe! I found it on pinterest and thought it turned out delicious! And the friends I made it for devoured it as well. I definitely plan on making it again! If you’re curious, my post on it should be linked below
Shoshanah Most Recent Post: As American As..


6 Creative Culinary February 13, 2013 at 10:16 am

Thanks so much for letting me know Shoshanah; I know we sure love it!


7 darlene October 8, 2012 at 11:03 am

this recipe is almost-exactly like the one i use and mine is from the *joy of cooking,* p. 661, (circa 1975 — no updated version[s] for me, please) … an amazing *old school* cookbook that still rocks out the goodies … anyway, i digress … i have never used fresh pineapple, but they are so *available* now — costco’s right down the road — that i’m going to have to try it …

also, a tip: i use my very old, well-seasoned, smooth-on-the-inside, cast iron skillet (OMGosh, does it ever work well!), about 10″ or maybe a bit more — the 3 boxes of already-canned tomatoes are in front of the cupboard where the skillet resides so i can’t really check the size — anyway, i have two round pizza pans, one fits atop my pressure canner rendering it useable for boiling-water-bath canning w/o ruining the delicate fiddlededee of the pressure canner lid, whilst the other is the exact same size as the ….. 10 inch skillet, thereby making it perfect to lay on top of the skillet while i veeerrryyy carefully turn out the baked cake on it … sometimes i have been known to use a large dinner plate, but my skillet is large and it does not always go well with my katty-wampus balancing act …. anyway, give the pizza pan idea a try next time, and i know there will be a next time b/c this is soooo good ….

take a look at this cookbook; it’s very cool, rolled biscuits, p. 632 — always high, light and fluffy — sorry for the ramble ;-))) …. darlene

ps … the *joy of cooking* ladies, the rombauer sisters, both deceased, don’t add rum TO the cake, they sprinkle rum (or brandy — so it says) on TOP of the cake and let it soak in ….


8 addie @ culicurious October 4, 2012 at 5:29 am

Oh I LOVE pineapple upside down cake!! YUMMMMM This one looks like a real winner :)


9 Creative Culinary October 5, 2012 at 10:29 am

Thanks Addie. Um…I might have had to freeze a bunch of it so I would stop having it for breakfast. Just one of my very favorite.


10 Tandy October 4, 2012 at 3:33 am

I really must try and make an upside down cake :)
Tandy Most Recent Post: Lavender And Lime Cheesecake


11 Creative Culinary October 5, 2012 at 10:30 am

Yes you must! The most difficult part of this one? Flipping over a 12 inch cast iron skillet and a 15″ plate. Not for the faint of heart I’ll tell you that!


12 Terra October 2, 2012 at 10:03 pm

I love hearing about your recipe card, and how loved and faded it is! If pineapple upside-down is out of style…..wellllll people are JUST crazy!!! Your cake looks fantastic, love the addition of pecans:-) Yum, Hugs, Terra


13 Creative Culinary October 5, 2012 at 10:34 am

Amen! I always laugh when some pompous person makes a statement like that. Some vintage foods I hope will never fade from our recollection.


14 Jenn October 2, 2012 at 3:49 pm

Yay, I’m so glad you could join in! And thanks for sharing such an informative history (and tasty looking recipe) about pineapple upside-down cake for the Monthly Mingle!
Jenn Most Recent Post: Naturally GF Links Roundup – September


15 Creative Culinary October 5, 2012 at 10:35 am

You know you are welcome…and of course, it meant that I had my favorite on hand too. We all won!


16 Carol Sacks October 2, 2012 at 3:46 pm

Gracious, Barb! Call it old-school, vintage, whatever you want, but give me a slice now! Fun post!
Carol Sacks Most Recent Post: Pear Almond Pie with Figs from Melissa Clark


17 Creative Culinary October 5, 2012 at 10:35 am

I just call it good. :) And, well…gone.


18 Kristen October 1, 2012 at 1:03 pm

Timeless and vintage sounds good to me, as long as we’re talking about cake and not my age :)
Kristen Most Recent Post: Simple Joy {Recipe: Rainbow Tie-Dyed Sugar Cookies}


19 Creative Culinary October 1, 2012 at 4:13 pm

You are a youngster. Hush.


20 Chung-Ah | Damn Delicious October 1, 2012 at 12:54 am

I don’t think I’ve ever actually had this before! I don’t know why but I need to get on this ASAP.
Chung-Ah | Damn Delicious Most Recent Post: Strawberry Frozen Yogurt #SundaySupper


21 Creative Culinary October 1, 2012 at 4:04 pm

Oh my gosh…then you have missed a treat. What I love about this recipe is that the cake is light and proportioned the way I like…I sort of consider it simply a holder of the wonderfulness of that pineapple business…it is ‘the bomb.’


22 Jean | Lemons and Anchovies September 30, 2012 at 8:18 pm

This was my favorite childhood dessert. It’s been a long time since I’ve had it and I thank you for bringing it back into my life. I can see the rum being a great addition. :)
Jean | Lemons and Anchovies Most Recent Post: Local Spotlight: Pescadero, CA (and Cinnamon French Toast)


23 Creative Culinary October 1, 2012 at 4:03 pm

Mine was always a tossup. This or German chocolate cake…and I love them both still today; maybe that will have to be next!


24 Katherine Martinelli September 30, 2012 at 3:50 pm

Love this classic!! Yours looks amazing.


25 Creative Culinary September 30, 2012 at 5:46 pm

Thank you Katherine…just wish I had some help eating it; made a HUGE cake and I’ve still got a lot left. Time to freeze and surprise myself someday down the road huh? :)


26 Paula September 30, 2012 at 2:28 pm

I’m actually surprised that food and desserts are even labelled *old-fashioned.* In my way of thinking, if you like it, if your family/friends like it then it is timeless. Proof right there in your grandmother’s handwritten recipe card. She baked it, everyone liked it and the recipe was shared through the generations and in your case, obviously treasured.
Easy to see why.
Paula Most Recent Post: Smurf Cookies – With and Without a Kopykake


27 Creative Culinary September 30, 2012 at 5:45 pm

Some youngster who knows nothing of tradition does that and then in 20 years they discover it and try to make it sound totally new. We just love it all along. :)


28 Mama's Gotta Bake September 30, 2012 at 9:45 am

You know it’s funny, but the pineapple upsidedown cake was out of fashion for awhile. And it’s one of my favorite desserts. But I’ve seen it make a comeback here in the restaurants in Los Angeles. I think the classic favorites really never go out of style. I will definitely give this one a try.


29 Creative Culinary September 30, 2012 at 10:00 am

I so agree with you; anyone who would call this old fashioned as if it’s not worthy has not had it! Vintage, classic…all those apply and I know my belly is happy I had a slice left this morning for breakfast with coffee. It’s true, I did that. :)


30 Rachel @ Baked by Rachel September 30, 2012 at 5:01 am

The words ‘or substitute’ should not have been uttered ;) Rum it is!
Rachel @ Baked by Rachel Most Recent Post: Maple Apple Chips {KitchenAid Giveaway}


31 Creative Culinary September 30, 2012 at 9:57 am

I know…you’re so right! I should just have a disclaimer for all of my recipes. If there is liquid involved, find some alcohol to substitute; that’s a better use of the word!


32 Baker Street September 29, 2012 at 8:09 pm

My family is a big fan of a pineapple upside down cake, actually any upside down cake. I’m yet to try the cherry cake you baked for my blog but I think using rum here might make me try this one first. Heh. Rum surely is a fantastic addition. Great recipe and lovely pictures, Barb. :)
Baker Street Most Recent Post: Homemade Blends: Apple Pie and Pumpkin Pie Spice Mix


33 Creative Culinary September 30, 2012 at 1:18 pm

That cake was good…but this is my all time favorite upside down cake. I would make it first too. :)


34 Holly September 29, 2012 at 4:37 pm

Mouthwatering photos! I think the addition of rum suits the cake perfectly, what’s not to like? My grandmother always made the boxed version of this cake; it is one of the desserts that I associate with her and it makes me smile to see it so beautifully done here.
Holly Most Recent Post: Brown Butter-Apple Butter Tart and #BaketogetherParty


35 Creative Culinary September 29, 2012 at 7:12 pm

Thanks Holly…I love how food can elicit such strong memories; I could almost feel myself in my childhood home baking this cake for the first time by myself. Well, minus the rum. :)


36 Laura (Tutti Dolci) September 29, 2012 at 12:48 pm

Rum is an absolute must in a pineapple upside down cake! This looks fabulous!
Laura (Tutti Dolci) Most Recent Post: apple, brown butter & maple blondies


37 Creative Culinary September 29, 2012 at 7:10 pm

Thanks Laura…it’s certainly a requierment for our from now on! Thanks for stopping by.


38 Renee - Kudos Kitchen September 29, 2012 at 11:33 am

Delicious post Barb! I’ll bet spiced rum would be a wonderful addition too. How could you go wrong?
I’m also a fan of pineapple upside-down cake. In my mind, it has never gone out of style.


39 Creative Culinary September 29, 2012 at 7:09 pm

Someone else mentioned that too Renee; I’ve got some that a brand sent me and didn’t think of it; heard it’s just seasoned with sugar and vanilla so I’ll remember that next time (and save the good stuff for drinks!).


40 Johnny West September 29, 2012 at 10:01 am

That looks perfect! I make one using a cast iron skillet and also one in a dutch oven while camping. I will definitely try yours with rum – bet it would be good with one of the spiced rums as well.



41 Creative Culinary September 29, 2012 at 7:06 pm

I have a spiced rum that was sent to me but the fellow at the liquor store said it’s terrible. Starts with Captain? I also hear the spiced is really just vanilla and maybe sugar? I should have used it and will for baked good and save the good stuff for sipping; thanks for the idea.


42 Suzanne September 29, 2012 at 9:23 am

Timeless and delicious, I don’t think a pineapple upside down cake could ever really go out of fashion it’s just so darn good, I love the rum, what a brilliant addition, Wish I could stop by for a slice, you did one of your Grandma’s proud.
Suzanne Most Recent Post: Meatloaf Plain And Simple


43 Creative Culinary September 29, 2012 at 7:05 pm

I feel the same way but I read that somewhere recently…not that I believe all I read! For me food is not about trends at all; I think some of them are horrible and I love the heritage/vintage, time worn recipes…they bring with them such memories. I honestly don’t think kale chips will be doing that. ;)


44 Lana @ Never Enough Thyme September 29, 2012 at 9:10 am

Pineapple + Rum = Yum!

I love making vintage family recipes and get so frustrated by cooks who disparage old recipes. Funny that some of them in the next breath will act as though they’ve just made the discovery of a lifetime and are actually speaking of something that has been around for 50 or more years, fallen out of style, and they’re just re-discovering and believing it new. Sigh.

I say let’s bring back the classics and really celebrate them!
Lana @ Never Enough Thyme Most Recent Post: Baked Apples with Cranberries and Pecans


45 Creative Culinary September 29, 2012 at 7:02 pm

You know how I feel. Some recipes are important traditions that we need to share and pass down; I honestly don’t think Oreo stuffing is going to stand the test of time. :)


46 Chris September 29, 2012 at 8:27 am

Who cares what is in fashion anyway. As long as it tastes yummy, I don’t care whether the recipe is 1, 30, or 1000 years old. This upside down cake looks delicious and … well, rum is involved … I see no reason why not to like it.
Hm, I can’t remember ever to have had an upside down cake.
Chris Most Recent Post: La Soupe Aux Choux – Herby cabbage Soup


47 Creative Culinary September 29, 2012 at 8:47 am

My thoughts exactly and yummy this is. You should make one; they’re really quite easy and so good.


48 Barbara @ Barbara Bakes September 29, 2012 at 7:53 am

Love the idea of using the biscuit cutter to cut out the core. Looks scrumptious!
Barbara @ Barbara Bakes Most Recent Post: Chocolate Cheesecake Cake


49 Creative Culinary September 29, 2012 at 8:50 am

You know how it is when you’re determined right? Well I was and was also lucky it was sitting right next to the cutter cutter I was thinking of using that was too big. Score!


50 Maureen | Orgasmic Chef September 29, 2012 at 7:14 am

I read that too but seriously… I’m ready to head back to the 80s to get this cake. The addition of rum is even better.
Maureen | Orgasmic Chef Most Recent Post: Asian Salad


51 Creative Culinary September 29, 2012 at 8:29 am

I say give me this over an Oreo stuffed cookie any day, right? Where’s that time machine, I’m ready!


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