[Note: This recipe got fresh photos in 2019 and we’re glad it did.]
I get so boring in the summertime. As soon as that warm weather hits and a bright blue sky becomes de rigeur and not something worth stopping the presses over, any near-religious attraction I had to the shiny and the new goes into hibernation until the fall. Do I want to start a sourdough that will take seven days to make? Well, since you asked, not really. How about that baked pasta dish that been buzzing like a bee in my bonnet for weeks? Um, well, maybe. If it rains or something and there’s nothing else to do. Do I want to try some new, crazy variant on a classic cake with cardamom? No, no, no!
Well, then what do I want to do? I want to go to the beach, and I want to go to barbecues. I’ve got goals, you see: I want to perfect the mint julep this summer and uncover a way to travel with all the trappings of a freshly squeezed Tom Collins. I want to bring buckets of just-made slaw, make more of my famous vegetable skewers that could fit on eight grills and I want to arrive with the kind of cake you don’t have to make a big deal out of; no frosting, no filling, no baubles, jimmies or piping and a minimal number of bowls. The kind of cake you’ve been eating your whole life yet a bite of it in the off-season will bring you back to a lazy spring weekend.
If you’ve stopped eating pineapple-upside down cake because you were rightly scared off by the seventies wallpaper-like pattern of rubbery pineapple rings filled with unnaturally bright maraschino cherries and the bland, almost pointless cake within that are all-too-accepted as the bakery standard, fear not, you can start again. Just two things separate a great pineapple upside down cake from a cake with, uh, pineapples on top are two things, three if you include the absence of red fruit-like gems: fresh pineapple and a layer of freshly-made caramel.
Don’t be put off by the caramel; if you have a 10-inch cast iron pan, you can make it right in the bottom, and use that as your baking dish. If not, it’s only one extra dish and takes less than five minutes to make. Fresh pineapple is the real turning point, though, and I was deeply saddened to not be able to find any this weekend (that is, until after I made the cake, naturally). It’s sharp, tropical flavor is unmatched by canned version, but in a jam, the can is your friend as it also comes packaged with the pineapple juice required for the cake.
And that’s all the fancy there is to this. You can make and bake in about an hour and a half, tops, and be that much more welcome anywhere you go. I know I was.
Pineapple Upside-Down Cake
Adapted from Gourmet, February 2000
The original recipe for this cake had three teaspoons of cardamom in it, alternately loved and loathed by recipe reviewers. I just wanted a classic pineapple upside-down cake and left it out, yielding the most flawless and easy go-to upside down cake, something I look forward to making every summer.
In the updated photos from 2019, I cut the pineapple into thin slices (I’d aim for 1/4-inch, no thicker) and use a small round cookie cutter to remove the core, overlapping the slices slightly. Since I have kids now and it’s apparently the Right Thing to share cake with them, I don’t drizzle the final rum over the cake anymore, but I do bake a little in. If you’d like to skip the rum in the cake altogether, simply use one additional tablespoon pineapple juice.
1/2 medium pineapple, peeled, quartered lengthwise, and cored
6 tablespoons (85 grams) unsalted butter
3/4 cup (145 grams) packed light brown sugar
1 1/2 cups (190 grams) all-purpose flour
2 teaspoons baking powder
1/4 teaspoon salt
6 tablespoons (85 grams) unsalted butter, softened
1 cup (200 grams) granulated sugar
2 large eggs
1 teaspoon vanilla
1 tablespoon (15 ml) dark rum
1/2 cup (120 ml) unsweetened pineapple juice
2 tablespoons (30 ml) dark rum for sprinkling over cake (optional)
Special equipment: A well-seasoned 10-inch cast-iron skillet. If you lack a cast-iron skillet of this size, make the caramel in a small pot and scrape it into the bottom of a similarly-sized cake pan. (I used a 9″ cake pan in the pictures above.)
Preheat oven to 350°F (175°C).
Make topping: Cut pineapple crosswise into 3/8-inch-thick pieces. Melt butter in skillet. Add brown sugar and simmer over moderate heat, stirring, four minutes. Remove from heat. Arrange pineapple on top of sugar mixture in concentric circles, overlapping pieces slightly.
Make batter: Sift together flour, baking powder, and salt. Beat butter in a large bowl with an electric mixer until light and fluffy, then gradually beat in granulated sugar. Add eggs, one at a time, beating well after each addition. Beat in vanilla and rum. Add half of flour mixture and beat on low speed just until blended. Beat in pineapple juice, then add remaining flour mixture, beating just until blended. (Batter may appear slightly curdled.)
Spoon batter over pineapple topping and spread evenly. Bake cake in middle of oven until golden and a tester comes out clean, about 35 to 45 minutes (I find this cooks more quickly in a 10-inch skillet). Let cake stand in skillet five minutes. Invert a plate over skillet and invert cake onto plate (keeping plate and skillet firmly pressed together). Replace any pineapple stuck to bottom of skillet. Sprinkle rum over cake and cool on plate on a rack.
Serve cake just warm or at room temperature.
Do ahead: Cake may be made one day ahead and chilled, covered. Bring to room temperature before serving.