After starting my Church Cookbook Series recently, my husband asked me to make what he said was his favorite cake — a Pineapple Upside-Down cake. I thought for sure I would find the recipe in one of my church cookbooks, but I came up empty handed. I was kind of surprised, but decided maybe it was either a little old fashion or too fussy for the Church Ladies. My vintage 1961 Betty Crocker Cookbook came to the rescue — but not easily. This cake was not listed in the cake section, but in the “Desserts”. I guess when you gussy up a cake it becomes a dessert. Go figure.
This is also sometimes called a “skillet cake” according to Betty and for this recipe it is baked in a 10 inch heavy skillet — I used one of my antique cast iron skillets, but you can also bake it in a 9×9 inch square pan or a 10 inch round cake pan. I will say that the pineapple circles fits perfectly in the 10 inch pan with 6 around the edges and one in the middle. As Betty says, “It is a handsome dessert to serve at the table.”
The irony of making a cake your husband hasn’t had in 40 years and only remembers his mothers version is that no matter how wonderful something is it never going to be as good as his mom’s. Not deterred by this fact, I gleefully baked this pretty cake and excitedly served him a warm piece and waited for his praise. As he takes a bite, he suddenly remembers his mom used “crushed” pineapple not rings! This might have been useful information when I was making it. After he said this, I insisted Betty would never use crushed pineapple instead pineapple rings — how could she sacrifice the stunning look of this dessert for crushed pineapple — never. I tried to convince my hubby that his mom must have just done that because it was easier, less expensive or something. Then it happens — I am reading the recipe for this blog and NOW I see it there in parenthesizes – (crushed maybe used if well drained). Dagnabit! Don’t tell Eric — I’m pretty sure I had him convinced. Next time, however, I will try it the way his mother made the cake. He did have some good points, which make me think his engineering background might have a little to do with them –it is easier to eat when you don’t have to cut through the pineapple ring and had more pineapple taste in every bite. And next time I hope I can make the cake he remembers!
Moral of the story is if you are trying to make something you or someone else remembers fondly — ask lots of questions so you can find a recipe that most closely resembles that memory. This cake really looked gorgeous and was moist and delicious, but it wasn’t his memory. My opinion — I think you will be pleased whether you are going for stunning look or practical version either way you make it you will be the queen or king of cakes.
Keep it simple and enjoy!
–Mary
Melt 1/3 cup of butter in a 10 inch skillet
Sprinkle 1/2 cup packed brown sugar evenly over melted butter
Arrange pineapple on the butter-sugar coating — Decorate with cherries and optionally pecan halves
Mix flour, sugar, baking powder, and salt in mixing bowl. Add shortening, milk and flavorings. Beat for 2 minutes. Add egg & beat another 2 minutes.
Pour batter over fruit. Bake 40 to 50 minutes.
Immediately turn upside down on a serving plate. Leave the pan over the cake for a few minutes to let it drop out naturally — my husband pulled it off too fast and we had a little messier cake than if it dropped out naturally.
- ⅓ cup butter
- ½ cup butter sugar (packed)
- 1 can sliced pineapple, drained (crushed may be used if well drained)
- 1½ cups of all purpose flour
- 1 cup sugar
- 2 tsp baking powder
- ½ tsp. salt
- ⅓ cup soft shortening
- 1 tsp. vanilla
- ½ tsp. lemon flavoring, if desired
- 1 egg (1/4 to ⅓ cup)
- ¾ cup milk
- Heat oven to 350 degrees. Melt butter in heavy 10" skillet, or pour melted butter in 9x9 pan or 10" cake pan.
- Sprinkle brown sugar evenly over butter.
- Arrange pineapple in attractive pattern on the butter-sugar coating.
- Decorate with pecan halves and cherries if desired.
- Measure flower by dip-level-pour method or by sifting.
- Stir flour, sugar, baking powder, salt in mixer bowl.
- Add shortening, milk flavorings.
- Beat 2 minutes on medium speed in mixer or 300 vigorous strokes by hand.
- Scrape sides and bottom of the bowl constantly.
- Add egg.
- Beat 2 more minutes, scraping bowl frequently.
- Pour batter over fruit.
- Bake 40 to 50 minutes.
- Immediately turn upside down on serving plate.
- Leave pan over cake a few minutes.
- Serve warm with whipped cream
This recipe brought memories back as I remember making one of these in school many years ago, if I’m being honest I cant remember how it tasted (probably not very good but my baking/cooking skills have improved since then!). Might give one of these a bash again but will need to make a gluten/dairy free version now though 🙂
Denise | The Life of Dee
My daughter needs to be dairy free — I often use butter flavored Crisco as a replacement for butter in baked goods — some of the butter replacements like Smart Balance also work pretty well. I’d just watch for water content in this one. I haven’t done a lot with gluten free flours and textures using them, but I think they are getting much better these days. Good luck — I’d be interested in hearing how it comes out.
A pineapple upside down cake is one we used to make while camping. Yes in a 10 inch covered cast iron pan or if we had a crowd in a 12 inch. We have dazzled some friends by making it in the summer too in our back yard. There is a formula of how many charcoal briquettes on top and bottom. I always make it with rings. It is so pretty. That said I do understand using the crushed so more pineapple in every bite!
As a kid I loved Hermit cookies a friend’s mother made. I got her recipe and made them and I guess my tastes have changed in 40 years.
Looks and sounds yummy, been many years since eating my Grandmas pineapple upside down cake…recipe looks easy enough, now if someone would just make it for me..
Now Renee — you could probably handle this one! LOL
I love vintage recipes. This looks so yummy Mary. I like to take a vintage recipe and remake it skinny!
I carefully reread this and don’t see the quantity for milk but my memory tells me 2/3 c. 1/3 combined and beat on low and then 1/3 included. I’m pretty old and made this frequently for my family.
You are so correct — thanks for the good catch! 3/4 of a cup is what the recipe I used had for the quantity of milk, however, when I did a quick Google search I found multiple Betty recipes of varying quantities — some had no milk at all and used the pineapple juice. The recipe with 1 1/3 cup of flour called for the 2/3 cup of milk as you mention and the one I have with 1 1/2 cup of flour calls for 3/4 cup. I’ve updated the recipe. I guess I need a better proof reader than me! Have a great day!
Hi there, if you’ve updated (re: the milk..) I’m not seeing it!? Glad I read the comments though, and maybe you want to update the ing. list to include the milk, which doesn’t seem to be listed at all?
Thanks — I have it updated now — I had 2 recipes one that called for milk and one without…but appears I posted the one that was supposed to have milk without it…duh. Thanks!
No milk listed in ingredient list.
Thanks — I added it again – apparently I didn’t update it properly the last time!
I made this recipe from my 1961 Betty Crocker Cookbook. The milk is 2/3 cup not 3/4. I used oil instead of shortening. I bake mine in a “8” cast iron skillet. I pulsed a can of chunk pineapple which was well drained first and then again after processing. Had rave reviews by the dancers at my Sunday Aledo Dance Class. I was impossible to find the original recipe on the internet. I had requests for the recipe. Thanks for your submission.
There does seems to be a thousand recipes — some with no milk, Betty in 1986 decided 1/2 cup was good enough — I think you could use any good yellow cake recipe and do the topping and it would be wonderful!
The original recipe calls for 3/4 cup pineapple juice, no milk
I am 86 still using my 1950 Betty Crocker cookbook.