My grandma Ann used to make a classic pineapple upside down cake in an ancient skillet with lots of rum. She’d serve it with ‘satin sauce’ which was some sort of special whipped cream reserved only for grown-ups. It felt like the fanciest thing I’d ever seen.
How did the pineapple go from the bottom to the top? What did rum taste like? How do you even make caramel? Once I grew up a little and discovered rum was really not for me (you learn a lot in college), I also decided that pineapple upside down cake was very much not cool. I went to culinary school in Manhattan in my early twenties in the mid-2000s. Go ahead, do the math, I’m old. At that time everything was either miniature, a cupcake or both. I never thought much more about that pineapple upside down cake until recently. If you think about it, it’s sort of the perfect dessert. It comes out of the oven ready for its beauty shot, no fancy piping required. It also comes ready to go with a gorgeous caramel sauce. You can make it with almost any fruit, and although it seems fussy, it’s a breeze to pull off.
In this version I’m using blood oranges because they are in season and give the cake a beautiful jewel tone. Any type of orange you prefer would work here, you just want to make sure you cut them into thin, even wheels. I added bourbon to the caramel because YOLO, but you can skip it if you learned in college that bourbon is not your thing.
Blood Orange Upside Down Cake
- 4 tablespoons butter, plus more to prepare the pan
- 1/2 cup light brown sugar
- 1 tablespoon bourbon
- 4 medium blood oranges, skin and pith removed, cut into wheels
- 1 1/2 cups all purpose flour
- 1/2 teaspoon baking soda
- 1/2 teaspoon kosher salt
- 1/4 teaspoon baking powder
- 1 cup sugar
- 2 small oranges, zested
- 2 eggs, at room temperature
- 1/2 cup olive oil
- 1/2 cup Greek yogurt, at room temperature
- 1/4 cup fresh squeezed orange juice
- 1 teaspoon vanilla extract
For the Caramel and Oranges:
For The Cake:
Preheat the oven to 350˚F. Butter an 9-inch cake pan. Place the butter in a medium heavy-bottomed saucepan and set over medium heat until melted. Add the brown sugar and bourbon and cook, stirring often, until the sugar has completely melted, about 4 to 5 minutes. Pour the caramel into the bottom of the prepared baking dish, then working quickly, arrange the orange wheels on top of the caramel, working to fill the entire bottom of the pan. Set aside.
To make the cake batter, in a medium bowl sift together flour, baking soda, salt and baking powder. Set aside.
In a separate large bowl, combine the sugar and orange zest and massage with your fingers until evenly combined. Whisk in eggs, olive oil, Greek yogurt, orange juice and vanilla. Add the dry ingredients and fold until no streaks of flour remain.
Pour the batter into the prepared pan and smooth into an even layer.
Bake for about 35 minutes, or until a cake tester inserted in the center of the cake comes out clean. Cool the cake for 10 minutes, then run a knife around the edge to loosen it from the pan. Invert the cake onto a plate or platter and say a prayer. You should hear it sort of thump out. If needed, gently tap on the bottom of the pan with a wooden spoon to loosen it. Let cool completely before serving.
I’ve had the bourbon shortbread cookies and they taste like a true “Old Fashion”.
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