Oh, you knew this was coming. How could I not have this in my repertoire? The thing is, although this is simple and I think it’s delicious, I make this very rarely. I did recently but not for years before that. I remembered I used a boxed cake mix. When it comes to boxed cake mixes I am an uberfan. Off to the Betty Crocker website I went and found two pretty much identical recipes, except for one you use a bundt pan and for one you use an oven-proof skillet. You can also use a cake pan, an 8 X 8 or 9 X 13 baking dish, etc., but the ingredient amounts will vary.
I’ll do the bundt pan one first, because that’s more fun, and that’s the one I actually did, and then the skillet one. You’ll see how twinsies these are. So without further ado…
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Pineapple Upside-Down Bundt Cake
2 tbs. butter, melted
1/4 cup packed brown sugar (“packed” in this sense means you don’t just pour it into your measuring cup, you tamp it down with spoon so you get the full mount without a lot of air)
6 pineapple slices from a can. Slices, so pineapple rings, not chunks. These seem to come in standard depths and diameters, but make sure you get 6 of them.
6 maraschino cherries. Maraschino cherries are surprisingly ubiquitous. You probably overlook them but your grocery store should have them. These are also eerily standard-sized.
1 box of Betty Crocker Super Moist yellow cake mix. This is important, because Bets produces 50 or 60 different varieties, so go for this one. These boxes are also standard-size.
1 cup of the pineapple juice your pineapple rings came in
1/2 cup vegetable oil
3 eggs
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Preheat your oven to 350 degrees. In a bundt pan sprayed with non-stick cooking spray, pour in the melted butter. Spoon over an even layer of brown sugar. Arrange your six pineapple rings in a ring on top of this. In the middle of each pineapple slice place a maraschino cherry.
In a bowl, mix the cake mix, the pineapple juice, the oil, and the eggs slowly until everything’s combined. Then mix on high speed for 2 more minutes. Pour this into the bundt pan over the be-maraschino’d pineapple slices that are lying on their bed of butter and brown sugar.
Put this in the oven for 40—45 minutes. Your cake will be a nice warm golden brown, but also do the toothpick test just to make sure. Take it out and let it cool down for a few minutes. Now place whatever you’re going to serve this on (a heatproof plate or whatever) upside down over the pan and *carefully* flip it over. You do this carefully so that the pineapple slices with their cherry centers stay in place. Do it quickly though so it doesn’t slip around. The non-stick cooking spray should ensure that it comes right out. Remove the pan and there you have it!
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Pineapple Upside-Down Skillet Cake
[Not personally vouched for by the Cousin Matthew Test Kitchen™ but this will surely work just fine]. You’ll need all of the above, but 12 pineapple slices instead of 6, 16 maraschino cherries instead of 6, 3 tbs butter instead of 2, and 1/2 cup of packed brown sugar, not 1/4.
Experience a sense of déjà vu. Preheat oven to 350 degrees. In a large, oven-proof skillet, pour the butter in an even layer and then the brown sugar, as above. Layer in 8 of the pineapple rings so they cover the bottom of the skillet but don’t overlap, like in a honeycomb pattern. Each one gets a cherry in the center. Slice the remaining 4 in half and arrange those 8 halves along the sides of the skillet sort of “face up” so they’re smiling at you, not frowning. Place a cherry in the hollow of each half ring.
Prepare the cake mix as above and pour into the skillet, being careful that your pineapple-half fence maintains the position. Into the oven it goes, same 40—45 minutes, let cool for a few minutes, top with the upside-down serving plate big enough to catch all of this, and flip, carefully. Everything should hold together.
Whichever way you do this, rejoice in the fact that it’s 1959 and Hawaii has just been admitted to the union, so there’ll be more pineapples stateside than ever!
I’m all about the cherry in the center! Yummy, Cousin M!
This was my father’s savorite cake, I always made it for his birthday. I do mine in a cast-iron skillet and add bourbon to the brown sugar and butter mixture.
Came here to be Team Cast Iron Skillet. Sooo, soooo good.
So I’m one of those fat adults that was a chunky kid. And to my everloving frustration, we actually didn’t eat bad. My dad’s little sister was diagnosed as type 1 diabetic in the 1960s, so he grew up where you didn’t have rolls, didn’t have candy, didn’t have dessert, etc etc etc. This was just how we cooked when I was a kid in the 80s and 90s, too.
Not a household where we had bread with meals, so my definition of a “fancy” meal or restaurant was where you had rolls, especially crescent rolls. We didn’t have dessert in the house except maybe once a month, we didn’t even have soda in the house until I was in high school. And yet I was still a chunk. Really unfair in retrospect.
But I digress.
Pineapple upside down cake was an extra fun bonus dessert because it didn’t require the entire can of pineapple rings and juice and my mom would let me have the extra in the can as a treat!