Pineapple Upside Down Cake

June 5, 2024

Mister Sive sharing a super yummy dessert recipe on this Wine & Dine Wednesday that was sooooooo good. Take it away TPS!

A few weeks ago, we had some dear friends stay with us at Hawthorne, a couple one half of whom I’ve known since college days, along with their daughter, and the daughter’s beau, a delightful fellow from the Emerald Isle (aka Ireland). (Come to think of it, fitting for a young woman raised in the Emerald City!) TKW cooked a pretty classic American meal of baked chicken, fab smashed potatoes, and roasted veggies, so I thought the dessert should also be some classic Americana, especially for those of us raised in the mid-to-later depths of the last century: Pineapple Upside Down Cake! This version varies a bit from Craig Claiborne’s New York Times Cookbook of 1966.

Take out your lasagna pan (!), at 9×13 the perfect size. Preheat the oven to 375. Melt 1/3 cup of butter, spread evenly in the baking pan, and then spread 1 ¼ cup of dark brown sugar on top of the butter. Peel and cut a fresh pineapple (the Clairborne recipe of course calls for canned!), and layer ½ inch thick slices on top of the butter/sugar mixture in whatever pattern strikes your fancy, leaving room for the nuts and other fruit—this will take likely 1/3 of the entire pineapple. 

Then, in the spaces between the pineapple slices, place ½ cup or more of whole pecans. 1/3 cup or so of whole cherries is also fun, optionally, placed between the pineapple and the pecan. Remember in all this that the bottom of the pan becomes the top of the cake, so place the prettiest sides of the food upside down. 

Cream ¾ cup of butter with ¾ cup of granulated white sugar until light and fluffy. Then beat in one egg and one egg yolk, and 1 teaspoon vanilla. Sift together 2 ¼ cup flour, 2 ¼ teaspoons of baking powder, ½ teaspoon of salt, and then mix this in with the butter and egg mixture, in 3 or 4 batches, alternately with ¾ cup of milk.

The batter will be malleable, but a bit thick. Spread carefully over the pineapple and mixins, and bake for about 35 minutes or until an inserted toothpick comes out clean. Let the cake cool for only about 5 minutes, run a knife along the edges, and then invert onto a serving platter. This cake works well as a leftover, just nuke individual servings for 20 seconds or so before serving. 

Serve as it is, or with ice cream or whipped cream, and think back on your own childhood dessert memories!