Pineapple Upside Down Cake

You might think this an odd time of year for pineapple upside down cake, and maybe it is, but it's also one of my most favorite cakes. For as much as I love chocolate, I would choose a nice caramelized pineapple upside down over a chocolate cake or brownie for my birthday any day of the week. And that's just what I did about 25 years ago when my mom invited me and my family to celebrate my birthday at her house for dinner.

Mom informed me that my brother and sister and their families would be there and asked what I would like for dinner and a cake. I asked for any kind of pasta (it was a Sunday after all) for dinner and a pineapple upside down cake for dessert.

Now if you know anything about Italian families, before girls started to grow up and keep their last name and then give it to their children, boys were the key to carrying on the family name. That's the era that I grew up in, so the responsibility (and the homage) sat with my brother. In our house growing up it felt like, at least for Mom, the sun rose and set about my brother.

Now you might think.... sibling rivalry -- at her age? No, I literally can count a dozen friends from Italian American homes who all have experienced the 'my son, my son' mentality from their mom when growing up. Anyway, I bet you're wondering where this is going, well you're about to find out. Let's go back to my birthday dinner.

We load our kids in the car and make the 1+ hour trip to mom's house in the middle of January (yep, my birthday is just around the bend) for my birthday dinner. Dinner is served and it's a pork loin which was then my least favorite food on the earth because mom cooked it until it was gray leather to avoid trichinosis or some such thing. Anyway, I ask about why we're having pork loin and if there's a pasta course coming. Mon says, "Pork loin is your brother's favorite." OK, his birthday is in August.....

So I choke down the meat, looking forward to the cake. We clear dinner away, make the coffee, I get sent to sit, the lights go out, the cake with candles ablaze comes out and everyone singing. I blow out the candles and notice that the cake has chocolate frosting. I look up with a puzzled gaze at my mom who tells me that my brother's favorite cake is spice with chocolate frosting. I am totally sure this was January and not August, the snow on the ground was a great indicator.

Pineapple upside down cake with a perfectly caramelized topping.

Needless to say, I stopped accepting birthday invitations to my mom's and made myself that pineapple upside down cake the following week.

Now that I've had my rant, old wounds die hard, I'll talk about how my mother-in-law Rosalie taught me how to REALLY make the cake. I must have been whining about the dinner at my mother's and Mom Scheckel asked if I ever made pineapple upside down cake in cast iron. She explained that the butter and brown sugar caramelize much nicer in the heavier cast iron. SO... that brought about a whole new dimension to pineapple upside cake for me and now I love it even more.

THE RECIPE:

This is a combination of the ingredients from my mother's recipe and the cooking method from my mother-in-law's. You'll need a cast iron dutch oven or a fryer pot that's at least 4" deep. You'll also need a good set of oven mitts when it's time to take the cake out of the oven. It will work in a regular aluminum cake pan as well but the cooking time will be a bit less and the top (once inverted) just won't be as caramelized and gooey.

1 can sliced pineapple in real pineapple juice

1 yellow cake mix

eggs per the cake box instructions

cooking oil or butter per the cake box instructions

come water

A dozen or so cherries

1 stick of salted butter1-2 c dark brown sugar

Drain the pineapples and reserve the juice.

Preheat the oven to 375 degrees

While the oven is heating, place the full stick of butter in your baking pan and heat in the oven or on the stove until the butter is melted -- keep an eye not to let it burn.
While the butter is melting prepare cake mix according to instructions, BUT use the pineapple juice to replace the water. You may still need to top it off with water, but definitely use the juice. I keep little 6 oz. cans of pineapple juice so I can use all juice and not dilute with water.
Carefully remove the pan from the heat and make sure the butter is distributed evenly in the pan.
Distribute the brown sugar to evenly to cover the bottom of the pan.
Carefully place the pineapple slices to cover the pan, you can cut some in half or quarters to get the best coverage.
Place a cherry at the center of each whole slice and in any larger gaps.
Make sure the fruit is pressed into the brown sugar / butter mixture so it doesn't move when your pour the cake batter in.
Pour the cake batter over the fruit and bake.
Bake at 375 degrees for 10 minutes or so and then reduce heat to 350 degrees and start checking for doneness at about 45 minutes -- especially if you're using an aluminum pan. Cast iron typically takes up to an hour. When a toothpick comes out clean, it's done.

When you take the pan out, while it's still hot, CAREFULLY invert in onto a plate. You might hear the cake drop to the plate, and you might want to peek, but DON'T do it. Let the cake sit until the pan is cool enough to remove with your bare hands.

Carefully lift the pan straight up. If by some chance, anything is stuck to the pan, carefully remove it and place it on the cake.