Pineapple Upside-Down Cake with Toasted Coconut Ice Cream

If you’ve ever seen “Fiddler On The Roof,” you probably know the term “yenta.” A yenta, in Yiddish, is a busybody, a meddler; in “Fiddler,” though, she’s a specific person, a matchmaker.

My whole life, I’ve always been something of a yenta. I love to get involved with people’s life decisions, telling people where to work, where to live, who to date. I’m kind of annoying that way. Which is why, over the years, I’ve pulled back a bit and let people lead the lives they want to lead, not getting too involved. And as far as matchmaking, occasionally I’ll set people up–I have some successes under my belt, some disasters too–though now I think I’m better off applying my skills to food: which is why I decided to pair pineapple upside-down cake with homemade toasted coconut ice cream.

It doesn’t take a yenta to see that this is a very good match: both recipes involve somewhat tropical ingredients (pineapple, coconut, rum) and everyone knows that cake tastes better with ice cream and that ice cream tastes better with cake.

To start, you make your ice cream batter. I used a recipe from my favorite ice cream book, David Lebovitz’s “The Perfect Scoop.” It begins by toasting unsweetened coconut in the oven:


When you start to smell it (and it smells terrific) you know it’s ready:


You add that to a pot of warm milk, cream, and sugar, along with a scraped vanilla bean:


That infuses for an hour, and then you strain it, pressing hard with a rubber spatula to extract all that flavor:


You work that warm mixture into some egg yolks:


Then return to the pot to cook, very gently, scraping and stirring constantly until it’s thick and coats the back of the spatula:


Strain that into more cream:


And there you have it, your toasted coconut ice cream batter. Cover and chill for a few hours; while that’s happening, make your cake.

To start, cut up a pineapple:


You only need half, so cut that half in half and remove the core:


Then cut each quarter in half and into little slices that you’ll arrange prettily on the cake:


In a pot, cook some brown sugar with butter:


This isn’t very precise; the recipe–which comes from Smitten Kitchen–says to cook for 4 minutes. It’ll look something like this:


You could do all this in a cast iron skillet and cook the cake in there, but I’ve had bad experiences doing that before (see here; the cake wouldn’t come out of the pan) so I decided to spray a 9-inch cake pan really well and then to pour the caramel in there:


I didn’t worry too much that the caramel didn’t spread evenly; I knew it would remelt and re-spread in the oven. On top of that, I arranged the pineapple (be careful when you do this: it’s hot!):


The batter’s really easy—just butter, sugar, eggs, flour, baking powder, salt, and pineapple juice—and you pour it on top of your pineapple arrangement:


Into the oven it goes and it comes out looking like this:


Let it cool in the pan for a few minutes, then run a knife around it and place a cake stand (or plate) on top of the pan:


Hold your breath and flip!


Not bad, right? It also helps to bang on the pan a few times before lifting it off. And if pineapple does stick, you can always reapply it manually.

Finally, it’s time to churn your ice cream. That’s as simple as pouring your batter into an ice cream maker and switching it on:


When the ice cream is thick, you’re done:


Spoon it into a container and freeze until you’re ready to serve. It’ll firm up more and will make for nice round scoops.

And there you have it–a match made in heaven; even Yenta the Matchmaker would be proud. And, confession time: I left out the rum because I was too cheap to buy a bottle, but if you add rum to both the ice cream (as the recipe calls for) and the cake (as the recipe calls for) this match will sing even louder than this:

Recipe: Toasted Coconut Ice Cream

Summary: From David Lebovitz’s “The Perfect Scoop.”


  • 1 cup dried shredded coconut, preferably unsweetened
  • 1 cup whole milk
  • 2 cups heavy cream
  • 3/4 cup sugar
  • Big pinch of salt
  • 1 vanilla bean, split in half lengthwise
  • 5 large egg yolks
  • 1/2 teaspoon vanilla extract or 1 teaspoon rum


  1. Preheat the oven to 350 degrees F. Spread the coconut on a baking sheet and bake for 5 to 8 minutes, stirring frequently so it toasts evenly; when you start to smell it, check the color—it’s easy to go from brown to burnt, so take it out just as it looks toasted.
  2. In a medium saucepan, warm the milk, 1 cup of the heavy cream, sugar, and salt and add the toasted coconut. Use a paring knife and scrape all the vanilla seeds into the warm milk, then add the pod as well. Cover, remove from the heat, and let steep at room temperature for 1 hour.
  3. Rewarm the coconut-infused mixture. Set a mesh strainer over another medium saucepan (I just used a bowl and cleaned the first saucepan) and strain the coconut-infused liquid through the strainer into the saucepan. Press down on the coconut very firmly with a flexible rubber spatula to extract as much of the flavor from it as possible. Remove the vanilla bean pieces (rinse and reserve them for another use; I put mine in a jar of sugar to make vanilla sugar) and discard the coconut.
  4. Pour the remaining 1 cup of heavy cream into a large bowl and set the mesh strainer on top. In a separate medium bowl, whisk together the egg yolks. Slowly pour the warm coconut-infused mixture into the egg yolks, whisking constantly (you don’t want the eggs to scramble), then scrape the warmed egg yolks back into the saucepan.
  5. Stir the mixture constantly over medium heat with a heatproof spatula, scraping the bottom as you stir, until the mixture thickens and coats the spatula. Pour the custard through the strainer and stir it into the cream. Mix in the vanilla or rum and stir until cool over an ice bath (I skipped the ice bath and it was ok); then refrigerate for several hours until the mixture is very cool.
  6. When it’s ready, churn in your ice cream maker until thick (it takes 20 minutes or so) then spoon into a container and freeze until ready to serve.

Preparation time: 30 minute(s)

Cooking time: 5 minute(s)

Number of servings (yield): 8

Recipe: Pineapple-Upside Down Cake

Summary: From


  • 1/2 medium pineapple, peeled, quartered lengthwise, and cored
  • 3/4 stick unsalted butter (for topping) + 3/4 stick unsalted butter, softened (for cake)
  • 3/4 cup packed light brown sugar
  • 1 1/2 cups all-purpose flour
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla
  • 1 tablespoon dark rum
  • 1/2 cup unsweetened pineapple juice
  • 2 tablespoons dark rum for sprinkling over cake


  1. Preheat the oven to 350 degrees F.
  2. Make the topping by cutting the pineapple crosswise into 3/8-inch pieces. Meanwhile, spray a cake pan well with cooking spray. (This is if you’re not using a cast-iron skillet; if you’re using cast-iron, you can do everything in the pan… just make sure it’s well-seasoned before doing that.) Melt the butter for the topping in a pot and then add the brown sugar; stir and simmer over moderate heat for four minutes. Pour into the cake pan and then very carefully arrange the pineapple in a pretty pattern on top (careful, that sugar’s hot and it gets harder the longer it sits).
  3. Now make the batter by sifting together the flour, baking powder and salt. In a mixer, beat the butter until light and fluffy, then gradually add the sugar. Add the eggs, one at a time, beating well after each addition; add the vanilla and rum. Add half of the flour mixture and beat on low speed, then add in the pineapple juice, mix, and then the final flour mixture, just until blended.
  4. Pour the batter over the pineapple topping and spread evenly. Bake in the middle of the oven for about 45 minutes, until the cake is golden and a tester comes out clean. Let it stand in the pan for a few minutes and then place a plate or cake stand on the pan and flip it, carefully, upside down. Bang a few times before lifting: voila! There’s your cake. If any pineapple doesn’t come out, pull it out manually and arrange it on top.
  5. You can serve the cake warm or at room temperature.

Preparation time: 20 minute(s)

Cooking time: 45 minute(s)

Number of servings (yield): 8

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