If you grew up in the 1950's or '60's, chances are your mom or grandmother made a Pineapple Up-Side-Down cake on occasion. Most everybody I knew who made the cake used canned pineapple as it was more readily available than fresh then.
Canned will do in this recipe ~ but fresh just moves it up a notch.

When I saw a version that Tyler Florence serves at his San Francisco "Wayfare Tavern" restaurant I was reminded that I hadn't made this cake in a long time.
I wanted to make individual cakes but the dilemma was finding the right size baking containers. I have seen recipes where the cake is baked in jumbo muffin tins, but unless you get an exceptionally small pineapple, you have to trim the pineapple rings to fit. That idea didn't appeal to me so much, so I ended up using these little Chantal® crockery pie dishes. They hold about 11 ounces. If I had smaller suitable containers, perhaps an 8-ounce size, it would have worked out better as I felt this size portion was a little too large, we ended up serving 1/2 cake for each serving.

To me what makes this dessert really special is the combination of tropical flavors ~ so quite honestly, the next time I'd skip the hassle of making individual servings and just make the cake the usual way ~ in an 8 or 9-inch baking pan.
You'll get the same luscious flavors with a fraction of the work!
I'm all for that.
The Macadamia nut brittle is a nice extra touch, but it certainly could be omitted. It provides a nice counterpoint to the not-too-sweet coconut ice cream. For the brittle I just used my favorite nut-brittle recipe, substituting toasted macadamias and sprinkled a little Fleur de Sel on top while it was cooling.
To make assembly of the dessert easier, I made the brittle two days ahead and stored it in an air-tight container. I made the Coconut Ice Cream the day before, and baked the cakes the day of.
If you're looking for a great recipe for coconut ice cream, look no further... and it is as easy as can be.
I always use 'Coco Lopez Cream of Coconut'® (yes, the same ingredient that makes killer piña coladas.) I've tried other brands, but this one is the best, in my opinion. And even though it is sweet, sweet, sweet straight out of the can, by the time it is mixed with the milk and cream, it is just perfect and not cloyingly sweet at all.
You can also add toasted coconut to the ice cream, but this time I thought there was enough going on with cake and the nut brittle, so I left it out.
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About the cutter for fresh pineapple ~
I've used the plastic pineapple cutter, but unfortunately a plastic part broke after only a couple of uses, rendering it useless ... money wasted.
I like that this one is made entirely of sturdy metal, PLUS it cores and cuts the pineapple flesh into a hollow cylindrical shape so you can cut the pineapple into thick or thin rings or spears. For the cakes, I cut them thicker than canned pineapple rings, a delicious improvement!
It also leaves the pineapple shell in tact which allows you to serve tropical drinks in it (or use it as container for fruits, desserts, etc.)
Other suggested uses (from the label):
"Use it to chop & mince fruit, vegetables & hard boiled eggs. Great for breaking up ground meat as it browns. It can cut better into sugar/flour for recipes. Also great as a cookie/donut cutter"
AND, it is proudly made in the USA!
So, the verdict regarding this dessert?
1.) These are fabulous flavors that were meant to go together.
2.) Canned pineapple is okay, but fresh is far superior.
3.) The Macadamia Nut Brittle is delicious, and a nice extra but definitely not a necessary component.
4.) The Coconut Ice Cream put this over the top... (it has been a family favorite for years.) I urge you to try it even if you skip the cake.
And # 5... Ice Cream is a PAIN to photograph. Thankfully the room temperature was not too warm. :)
If you would like printable copies of the recipes, please check out my recipe blog HERE.
Thank you for stopping by today, friends!