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Looking to Make Special Surprise: Pineapple Upside-Down Cake in Cast-Iron Skillet

OK 'Hounds, need your help!
My sister and I were in dire housing straits, will be taken in by our aunt. She remembers a pineapple upside-down cake that our father (her brother, since deceased) used to make. She remembers the wonderful smell and delicous taste when he took it out of the oven.
We just took a tour of her (small) kitchen, and she produced - Wheeee!!! a cast iron skillet!!!
Well, our turn to pay back -
Once we're moved, we want to make a pineapple upside-down cake in her honor, using her cast iron skillet. : )
Your best recipes, PLEASE!!!

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  1. that's really thoughtful of you - i'm sure your aunt will appreciate the gesture :)

    here's an excellent one from Gourmet Magazine. limit the cardamom to 1 or 2 tsp, and add a little cinnamon & ground ginger if it strikes your fancy...

    3 Replies
    1. re: goodhealthgourmet

      Thank you goodhealth, this looks delicious!!

      1. re: aurora50

        Do heed the warning to go easy on the cardamom, unless you're familiar with it and know you want that flavor apparent. It's heady stuff.

        1. re: blue room

          I like to add a dash of spiced rum to the fruit initially, speaking of heady stuff.

    2. I still love Wolfgang Puck's recipe or is Sherry Yard's.... not sure. I made a few changes like adding dried cherries to it. Delisiously moist, I love the cake batter. I didn't use my cast iron on this one but it will give you and idea..
      Actually its the best recipe I've tried, and I've tried using fresh pineapple too, I really love this one.

      6 Replies
        1. re: aurora50

          dug up a few more for ya:


          i can't seem to find Sherry Yard's recipe from Spago that Chicklet mentioned above, but perhaps she'd be kind enough to paraphrase for you if you want it.

          1. re: goodhealthgourmet

            that foodblogga recipe looks classic, except that there's no fat (butter or shortening) in the actual cake. I'm trying to imagine how the cake part would turn out.

            1. re: missmasala

              ooh, and i just re-read it, and it also calls for baking in a pan, not a skillet. okay, forget that one! :)

              1. re: goodhealthgourmet

                I've made Puck's pineapple upside down cake in both a cake pan and skillet. With the skillet you get more crunchy edge and crust, they're both quite good. And actually, the recipe attached to that link is different. Come to think of it, I'm not even sure the one I have from his cookbook is hers, I guess since she does all of his pastry I thought it was hers, looking at it, I don't see her getting credit after all...hmmm.

          2. re: aurora50

            1 1/2 cups sifted flour -AP
            1 1/2 t baking powder
            salt - I use about 1/8 sea salt or kosher
            1/4lb butter - salted - this is different than the recipe
            1 stick of butter softened
            1/4- 1/2 cup of dried cherries soaked in hot water, drained well. Or you can use marachino cherries drained well, cut in half.
            1/2 cup baker's sugar (small grind) not necessary you can use regular)
            2 large eggs - room temperature - in a bowl to drop in one at a time - look for shells or
            I like to use a small strainer to remove the large white thing in the egg. Don't break the yolk.
            1 tsp tahitian or good vanilla (the recipe calls for extract)
            3/4 cup whole milk (doesn't designate what %fat)
            3 T butter- I use salted
            3/4 c packed brown sugar I use what I have - this is a difference
            3/4 can of pineapple chunks, drained well. Or you can use crushed, or whole, fresh pineapple too. I didn't have success the time I used fresh, I probably dry the fresh pineapple well enough..

            Preheat oven 350 F
            1. Spray the cast iron pan with non stick (I have a nice dark 9 inch cake pan-the results are really nice I think)
            2. Sift the dry ingredients 2-3 times - set aside
            3. Melt 3 T butter in the bottom of your pan, swirl it around to coat evenly tip to come up sides a bit, sometimes I use 4 T - Sprinkle your brown sugar spreading it nice evenly.
            4. Make the cake. I use a KA, but if you don't get another bowl for a handmixing.
            For the KA use the paddle attachment, beat the butter on high until its light and fluffy might take about a minute or so. Clean the sides of the bowl down with a spatula, also scrape the bottom of the bowl to pull up anything that's not getting mixed. Continue beating at high speed, now gradually add your sugar. Now add the eggs carefully one at a time, stop and scrape the sides, continue after each egg. Now lastly the vanilla. Mix at a slow speed, using a spatula add the dry ingredients alternating with the milk. Beat until the batter is smooth.
            5. Spread the batter evenly over the pineapple. Bake in the center of the oven middle rack, 35 to 40 minutes. use a tester straw looking for a clean straw, without any batter.
            Remove from the oven - place on a rack to cool - for about 5-10 mins. Then the tricky part is planning this so the brown sugar is nicely melted and you don't have problems getting it out of the pan. I've flipped it too soon before and there were small cracks in the upside down part, but I'd used rings that time. Take your time.
            6. Using mitts or hot pads, you'll need to place a plate or serving dish-flip carefully and gently.

            This is a cake I put out often for parties and gatherings, I've served it with and without whipped cream, with homemad vanilla ice cream and the plate is wiped out. The cake part is just the best.

            This is such a sweet thing to do for your aunt, I know I'd appreciate that someone did this for me, Good Luck! sharon

        2. It's such a great comfort food dessert! Make sure you time the removal (flipping out of the pan) carefully - 5 minutes is about right (wait too long, it can stick -)so pull it out of the oven and set that timer for 5 minutes.

          Cover leftovers at room temp, It's even better the next day.

          1. My grandmother's recipe, from my family cookbook (my notes in parentheses, and further explanation of my tweaks at the bottom):

            Put 1 c. brown sugar in the bottom of a #10 cast iron skillet - 1/2 stick oleo (I use butter) dotted on sugar - drain a can of pineapple slices (I reserve the juice) - place on sugar

            1 1/2 c. flour (see my notes at the bottom)
            2 t. baking powder
            1/3 c. shortening (again, I use butter)
            1 c. sugar
            1/2 t. salt
            2/3 c. milk

            Beat 2 minutes. Add 1 egg and beat 2 minutes more. Pour over pineapple. Bake 20-30 mins at 350.

            My notes: This was originally a typical WWII one-bowl economy/dinette cake, with few rationed ingredients like eggs and butter. Living as I do without ration books, I increase the flour to 2.5 cups, increase the butter in the cake to 1/2 cup, and add another egg. I also add a splash of vanilla, and sour the milk with 1/3 cup of the reserved pineapple juice before adding. I use the creaming method rather than beating everything together.

            This is a tried and true, classic recipe that has won over many a skeptic! :)

            1. When I think Pineapple Upside-Down Cake in Cast-Iron Skillet... I go for the Betty Crocker (red binder) cookbook.

              1. aurora50, what your dad made was probably more like the one from the foodblogga site that goodhealthgourmet posted or the one that LauraGrace posted below.

                2 Replies
                1. re: Wtg2Retire

                  Here's what I did last summer.....

                  Here is the the basic recipe we used to do. Another one was to use cherry pie filling and a chocolate cake mix, then serve with ice cream.

                  Pineapple Upside Down Cake

                  4 Tbs. butter
                  1 cup brown sugar
                  8 pineapple rings
                  8 maraschino cherries

                  Cake Batter
                  1 yellow cake mix
                  1 cup pineapple juice
                  1/3 cup water
                  3 eggs
                  1/3 cup oil

                  Prepare Cake Topping: Melt butter in bottom of a 12" Dutch oven. Sprinkle brown sugar evenly over butter being careful not to touch the sugar once it has begun to dissolve into the butter. Carefully place pineapple rings on top of the brown sugar, 7 around the outside and 1 in the center. Place a maraschino cherry in the center of each pineapple ring.

                  Prepare Cake Batter: In a mixing bowl combine cake mix, pineapple juice, water, eggs and oil; mix well. Spoon cake batter carefully over the top of pineapple rings. Spread batter evenly to edges.

                  Bake: Cover Dutch oven and bake usinge 10-12 briquettes bottom and 14-16 briquettes top for 45 minutes or until top of cake springs back when touched.

                  Let the cake cool for 10 minutes or so in the oven with the lid cracked. Next run a rubber spatula around the inside edge of the oven to loosen the cake. To turn the cake out, first lay a piece of parchment paper across the top of the oven so it lays flat and replace the lid so that it holds the paper in place. Make sure you have an available lid stand resting on your table for the next step. Using gloved hands place one hand on the lid and the other hand under the oven and carefully lift and flip the oven over so the cake falls onto the lid. Rest the oven upside down on the lid stand and tap the bottom and sides of the oven lightly with your hand to make sure the cake didn't stick. Then lift the oven off the lid. The cake will be resting on the parchment lined lid and can be cooled this way or slid off the lid using the parchment paper. Allow cake to cool slightly before service.

                  Serve with vanilla ice cream or whipped cream as topping.

                  Serves: 8-10

                  1. re: Johnny West

                    ....except I did it in a skillet. Here is a link to a cake thread we
                    do at Rick's BBQ forum.


                    Thanks for looking.


                2. Very nice of you to do this for your aunt!

                  An observation...

                  If it were me, I'd use a recipe from whatever all-purpose cookbook your dad would probably have used. That way the cake has a better chance of bringing back the memory.

                  No cardamom or rum or any other spices. The classic pineapple upside-down cake is yellow cake on top of the pineapple-brown sugar-butter business on the bottom.

                  Actually, you can use a yellow cake mix with the pineapple syrup as part of the liquid.

                  One last thing... Get the pineapple in heavy syrup, not juice.


                  8 Replies
                  1. re: I used to know how to cook...

                    Of the dozens of pineapple upside-down cakes I've made, I've never used pineapple in syrup -- in fact, I've never seen such a thing as far as I recall. I invariably find pineapple in juice.

                    But I wholeheartedly agree with everything else you said!! ;)

                    1. re: LauraGrace

                      Hi Laura!

                      I've found the kind in syrup 'sticks' better in the brown sugar. Also not quite as tart as the juice kind.

                      I have had to look for the syrup kind lately though. Does seem most is packed in juice. Maybe Dole has my sugar intake as a priority??? LOL!

                      Either way - pineapple upside-down cake is a winner in my book!


                      1. re: I used to know how to cook...

                        And if it goes over well, I like to make it with apples and cranberries rather than pineapples and cherries. Just so you don't get too bored.

                        1. re: coll

                          Wow! Thanks for all the replies, everyone!
                          Just have to decide which one to use, now....

                          1. re: aurora50

                            You haven't indicated the time frame for your dad's original. if it's anything older than 30 years, it was almost definitely along the lines of Laura Grace's recipe. Different spices and fresh pineapple might well make, objectively, a better cake, but your goal here is catering to nostalgia. Go with a basic, no-frills, canned-ring and maraschino cherry recipe.

                            That said, I've started using various fruits and different flavors of batter for upside-down cakes. i prefer them to frosted cakes. They can be simplified by using a regular cake pan lined with parchment. I mix butter with brown sugar and cinnamon, and put that on the bottom, covered with whatever sliced fresh fruit I am using, then the batter. Release and clean-up are simplified this way, though I do lose out on the nice crusty sides. I particularly liked rhubarb with spice cake and pineapple with coconut cake. Individual ones in muffin tins with paper liners work too. That way you can vary the fruits from cup to cup.

                            1. re: greygarious

                              gg, I couldn't agree more about the method being a real winner, and easy for a casual company dessert.

                              Do you have a favorite spice cake recipe? That rhubarb-spice cake combo sounds like a keeper for spring, if it ever gets here...

                        2. re: I used to know how to cook...

                          Card night with some friends this weekend, and even though I'm hosting, I would NOT be invited if I didn't make this cake, so I picked up a can of pineapple while grocery shopping today and -- what to my wondering eyes should appear but pineapple in syrup! For crying out loud! I don't know that I've ever seen (or noticed) it before! It definitely gave me a chuckle in the fruit aisle. Still got the kind in juice though, you know what they say about old habits!

                          1. re: LauraGrace

                            Gosh, LauraGrace, now I have to add pineapple to the shopping list! Gotta bake one SOON.

                            As for getting the kind in juice - like they say - don't mess with success!


                    2. Once it's cooked, does anyone think that fresh vs. canned pineapple is a biggie?

                      1 Reply
                      1. re: blue room

                        For nostalgia's sake I'd go with canned, as back in the day (as they say) for most of the country fresh pineapple was a rare sight indeed. And most canned pineapple, if not necessarily all of it, did come packed in syrup.

                        And I do tend to think that, as you suggest, once it's cooked it's cooked. The canned will certainly be sweeter.

                      2. I don't have a recipe to offer, but another little bit of advice. I once made an apple cake in my cast iron, and it tasted ever so slightly like onion. Maybe I just don't clean my cast iron properly, but my cake picked up the faintest hint of the savories I usually cook in it. Just give it a sniff before you use it ;)

                        3 Replies
                        1. re: Honestly Good Food

                          This may be silly, but I have one cast iron pan that I only use to make Tarte Tatin and a Swedish apple cake.

                          1. re: MMRuth

                            Hi MMRuth,

                            Not silly at all!

                            If you're going to take the time and effort to do a Tarte Tatin or an apple cake, the last thing you need is an aroma picked up from prior use of your pan.

                            I sure wouldn't want to have that happen...


                            1. re: I used to know how to cook...

                              Good point, folks.
                              I'll try to be careful and sniff, investigate, and clean carefully before I use it. : )

                        2. I made a pineapple upside down cake for thanksgiving. A standard "box" yellow cake works fine in a 12" cast iron skillet. Melt a stick of butter in the cast iron pan over med low heat. Add a cup of brown sugar, then line skillet with pineapples and cherries as desired (reserving pineapple juice for cake mix). Make cake mix as directed except use juice in place of water. Follow baking instructions for 13x9 pan (close enough).

                          12" cast skillet is close enough to 13x9 that recipes seem to work fine.

                          Easiest pineapple upside down cake imaginable, and got RAVE reviews despite 7 other dessert offerings (no pineapple upside down leftovers).

                          Btw, only let it cool about 10-15 minutes before "the flip". Too cool, and they start to stick.

                          Hope you enjoy this as much as my family did!

                          Best wishes,

                          6 Replies
                            1. re: Allthegoodnameswere

                              Thanks Art. Was the goo in the bottom sticky/solid enough not to spill during the flip? I made such a mess once that I wondered would it be better to cool longer, flip, scrape adhering fruit out of the skillet, and reassemble on top of the cake layer.

                              1. re: Joebob

                                LOTS of butter in there to start with is the key. Get the skillet hot first, then add too much butter, and go from there after it stops foaming. Still, you might get some hangup, but just keep your attention on the fact that Taste trumps Looks any day, and scrape off whatever sticks without fretting about it. It's still the best damn cake in the universe.

                                  1. re: Will Owen

                                    And if it does stick, you can heat it up just slightly and try again.