Pineapple Upside Down Cake

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I am not a stuff person by any means. I have no problem letting things go, I don’t worry when dishes break or clothes get stained, but I do have a prized cookbook that I would be very sad to see anything happen to - The Last Course by Claudia Fleming. Every time I think I have a new and original idea, it turns out Claudia Fleming already had it – pre 2001. It’s truly a shame that the book is out of print, copies sell for hundreds of dollars on Amazon and ebay. Every pastry chef  I know treasures their copy. The Last Course is also the book that made me fall in love with pineapple of all things. Caramelized with pink peppercorns, bay and vanilla and served with vanilla ice cream – pineapple is a magical thing.

I have been dreaming of a pineapple upside down cake with those amazing flavors and getting Erin McDowell’s Fearless Baker was just the inspiration I needed to actually do it. I riffed on her upside down cake recipe a bit here, ok I riffed a lot.  Her version includes graham flour (yum!) and is topped with tomato jam (hello!), but I did take her general proportions and the addition of crème fraiche in the batter (yum again!). I don’t think she will mind.

Pineapple Upside down Cake

Very loosely adapted from Fearless Baker By Erin McDowell

Makes one 9-inch cake


4 tablespoons (55g) unsalted butter, softened

1/2 cup (110g) light brown sugar

2 tablespoons rum

1 teaspoon pink peppercorns

1/2 vanilla bean, split

1 bay leaf

2 cups sliced pineapple (fresh or canned – you do you)

pinch salt


1 cup (220g) unsalted butter, softened

1/2 cup (100g) granulated sugar

1/2 cup (110g) light brown sugar

2 eggs

1 teaspoon vanilla extract

2 cups (260g) all-purpose flour

1 1/2 teaspoon baking powder

1/2 teaspoon baking soda

1 1/3 cups (320g) crème fraîche

1 teaspoon kosher salt

Heat oven to 350° F.

Melt the butter and brown sugar together in a 10-inch (or deep 9-inch) cast iron skillet set over medium heat. Whisk until the mixture is smooth and combined. Add the rum, peppercorns, vanilla bean, bay leaf, and a pinch of salt.

Turn the heat down to medium-low, add the pineapple and cook for a few minutes turning the pineapple over in the sauce occasionally until the pineapple begins to soften and release its juices. Off of the heat, use a slotted spoon to remove the pineapple from the pan into a separate bowl or plate, then carefully remove the pink peppercorns from the sauce – I know this is fussy, but you gotta do it unless you want to pick peppercorns out of your teeth. Add the pineapple back to the pan in an even layer - if you have extra pineapple (lucky) just eat it :) Set the pan on a baking sheet, and brush the sides of the pan with a bit of butter. 

To make the cake, in the bowl of a stand mixer fitted with the paddle attachment, cream the butter, sugar, and brown sugar until light and fluffy, 4 to 5 minutes.

Add the eggs one at a time, scraping down the bowl after each addition. Add the vanilla and crème fraiche and mix to combine.

In a medium bowl, whisk the flour, baking powder, baking soda, and salt to combine. Fold the flour into the wet ingredients then pour the batter over the fruit and spread into an even layer.

Bake the cake on the baking sheet until a toothpick inserted inserted into the cake comes out clean, 35 to 40 minutes. Cool the cake in the pan for 15 minutes, then run a spatula around the outside of the cake and invert the cake onto a cooling rack. Cool completely and remove the bay leaf and vanilla bean pod before slicing and serving. 

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Roasted Pineapple Ice Cream with Mascarpone and Black Pepper

Roasted Pineapple, Mascarpone, Black Pepper Ice Cream

I don't know about you, but when I think of combining of dairy and pineapple the "diet plate" at my local diner comes to mind. Well, if I am being completely honest, I think of the aforementioned diet plate in the 1980's. I like to imagine women dressed in spandex and legwarmers gathering after their morning jazzercise classes to share a low-cal meal comprised of a little cup of cottage cheese with canned pineapple on top, an egg white or two and a slice of tomato, maybe a slice of dry wheat toast if they're lucky, but I digress, I'm sure you didn't click on this post in hopes of reading about ladies in leotards. Let's talk about ice cream made from sweet caramelized pineapple and rich mascarpone cheese instead, sound good?

Roasted Pineapple, Mascarpone, Black Pepper Ice Cream

The base of this frozen treat is a cinch to put together, there is no cooking of custard, no waiting for it to chill before churning (no churning at all!), and when it comes time to add the black pepper you might be tempted to skip it but please give it a try. The small amount creates a gentle warmth which cuts through the richness of the caramelized pineapple and the ice cream base. If you want to torture your neighbors, leave your doors and windows open while you roast the pineapple because the scent is absolutely intoxicating.

Did I mention that you don't even need an ice cream machine to throw this together? The texture is unbelievably smooth and if your freezer is crappy like mine it will stay perfectly soft and scoopable even if it's been in there for a few days (good luck keeping it around that long). Maybe make it for your pops, I hear dads like bourbon.

Have a great weekend!

Roasted Pineapple Ice Cream with Mascarpone and Black Pepper

Roasted Pineapple Puree 

adapted from The Last Course by Claudia Fleming

This pineapple tastes great on it's own or on top of  store bought ice cream if you don't want to make your own.

1 cup sugar

1 medium pineapple, peeled, cored and cut into eight rings

1 vanilla bean, split lengthwise, seeds scraped

pinch salt

1 tablespoon bourbon

1 ounce butter

Preheat oven to 375º

1. In a large skillet, combine the sugar and 1/4 cup water. Cook the sugar and water, swirling the pan occasionally until the mixture if a deep amber caramel 5-7 minutes.

2. Add the vanilla bean seeds and salt and stir gently to distribute them then add the pineapple slices and vanilla bean pod. Slide the pan into the oven and cook until the pineapple is tender and translucent, basting every 10 minutes.

3. When the pineapple is cooked, remove the slices from the liquid and set aside. Put the skillet full of juices over medium heat, add the bourbon and simmer gently until the mixture has reduced by half, then whisk in the butter off of the heat. Reserve the liquid for serving.

4. When the pineapple slices are cool enough to handle, take 5 of them and pulse in a blender or food processor until they are chopped into very small pieces, but not completely liquid. Cut the remaining 3 slices into chunks and reserve to serve with the finished ice cream.

Black Pepper Ice Cream Base (no churning required!)

adapted from Everyday Food

1 14 ounce can sweetened condensed milk

4 ounces mascarpone cheese

2 cups heavy cream

1/4 teaspoon salt

1/4 teaspoon freshly cracked black pepper

1. In a large bowl, whisk together the condensed milk, mascarpone, salt and pepper.

2. In a separate large bowl whip the heavy cream to stiff peaks. With a rubber spatula, gently fold the whipped cream into the condensed milk mixture.

To Assemble

You'll need a wide, shallow glass or metal pan, roughly 9x9 inches

Black Pepper Ice Cream Base

Roasted Pineapple Puree

freshly cracked black pepper

Pour 1/3 of the black pepper ice cream base into the baking dish and smooth to even it. Dollop heaping tablespoons of the roasted pineapple mixture on the surface, about 1'' apart. Top with 1/2 of the remaining ice cream base, dollop with roasted pineapple, then finally top with the remaining ice cream base. If you have a bit of extra pineapple puree, just eat it! It's delicious on it's own. Smooth the top to cover most of the pineapple, then using a knife or toothpick, gently swirl the pineapple and base together. Be careful not to mix too much, you just want to create pockets of pineapple in each scoop. Crack a bit of fresh black pepper over the surface and freeze at least 4 hours before serving. Serve with the reserved pineapple slices and gently warmed pineapple caramel.