TIP 1 > Fresh pineapple is better than canned, but canned will still taste good once it has the butter-sugar caramel and cake all over it. Grilling the pineapple slices first also amps up the flavor. If you use fresh pineapple, taste-test it to make sure it’s sweet enough and, if not, sprinkle a bit of white sugar on it before using.
TIP 2 > Don’t worry about getting rings out of your fresh pineapple; slices will still look great (see photo). Chunks will work, too, but they might fall off the edges of the cake a bit.
TIP 3 > You can skip the coconut and make just a regular pineapple upside down cake. Or you can add pecans instead. Or throw everything into it. If you really want to go wild, add cinnamon or nutmeg to the batter, or a bit of cayenne pepper to the butter-sugar caramel.
TIP 4 > Whipped cream or coconut ice cream is nice if you want to gild the lily. Maraschino cherries are not recommended unless you like that sort of thing.
TIP 5 > If you want a less sweet version, reduce the butter-sugar amount; if you want it sweeter, increase it (it’s very accommodating, unlike other baking projects).
I’m starting with this recipe because the pineapple is the symbol for welcome, and this is the welcome cake that I make for my new neighbors. I developed this version after starting with America’s Test Kitchen’s (ATK) recipe and finding it pretty ordinary and too similar to many other versions. I wanted my version to be not just different, but delicious enough to tempt me all day as it sits on the kitchen counter.
As you will know by the end of this book, I have a love-hate relationship with America’s Test Kitchen. I love that its recipes are reliable and well-tested, but dislike how sometimes the recipes are overcomplicated yet bland. So, often I will use its recipes as a starting point and then tweak them for more flavor, more variation, and fewer steps. (I also don’t like ATK’s annoying habit of asking me to renew my subscription every other month and threatening to take my firstborn child if I don’t!) I thought that the ATK pineapple upside-down cake recipe had too large a cake-to-topping ratio, so I changed the proportions and modified the ingredients. For one thing, I prefer an 8” round pan for faster and more even cooking over the ATK-recommended 9” size. I also added shredded coconut for more flavor. I tried adding rum to make it piña colada-ish, but the real rum flavor cooked out, and rum extract seemed ridiculously expensive. If you use either one, let me know how it turns out.
To see the original recipe and compare it to my version, look on page 650 of the America’s Test Kitchen Family Cookbook, version
2005, or on page 658 of its version 2014. Here is my version.
2 sticks unsalted butter, at room temperature (kept
¾ cup packed brown sugar
4-5 cups drained pineapple slices or chunks – whatever
fits tightly in the bottom of your pan
1 cup flour
1 teaspoon baking powder
¼ teaspoon salt
½ cup white sugar
2 large eggs (extra-large eggs are okay in this recipe, but
not in all recipes)
1 teaspoon vanilla extract (preferably vanilla bean paste,
which has more flavor, and which you can get at Penzeys
Spices or Williams Sonoma)
¼ cup milk
½ cup coconut shreds
(optional; sweetened or unsweetened, your preference)
1 Preheat oven to 350°F.
2 Put 1 stick butter in an 8” cake pan or cast iron skillet.
3 When oven is hot, put the pan or skillet in the oven for 3-4 minutes until the butter is melted.
4 Stir in the brown sugar, then tightly pack the pineapple into it. If using pineapple chunks instead of slices, scoot them a little bit away from the edge of the pan before covering them with the batter so that when you turn the cake upside down, they won’t fall off the edge. Don’t ask me how I know to do this.
5 If using coconut, sprinkle it over the pine-apple. The coconut is better this way, instead of mixed into the batter.
6 In a medium bowl, whisk together flour, baking powder, and salt.
7 In a large bowl or mixer bowl, beat the other stick of butter with the sugar on medium speed until fluffy, about 5 minutes.
8 Beat in the eggs one at a time, about 30 seconds each.
9 Stir in the vanilla.
10 On low speed, beat in a third of flour mixture, then half the milk, then another third of the flour mixture, then the rest of the milk, then the rest of the flour mixture.
11 The batter will be thick. Spoon it evenly over the pineapple, smooth the top, then gently rap it on the counter to coax out the bubbles.
12 Bake for 40 – 50 minutes, depending on your oven. Rotate it halfway through, and pull it out when a toothpick comes out clean but still has a few crumbs on it.
13 Let it rest for 10 minutes, then put a plate over it, invert it, and let it rest for 1 minute before removing the pan. Let cool before serving.