Traditional Pineapple Upside Down Cake gets a slight upgrade with this Cast Iron Pineapple Upside Down Cake with Basil Rum Glaze that is absolutely incredible!
I really wanted to call this blog post: brown things are hard to photograph. I actually made this cake about a month ago, photographed it, and I hate the photos even though I love the recipe. So, I sat on it. Also, it’s not that it’s just brown. I used fresh pineapple and they weren’t perfectly round and I couldn’t get too many slices in my cast iron skillet (previous one was better). I could go on and on about the imperfection of my photography on this one but I published it. Because, well, life isn’t perfect. Sometimes the photos will have to be “good enough.”
To be clear, this cake is damn delicious and in person, it was lovely. I’m a perfectionist and I’m REALLY working on my photography right now. I actually made and photographed these Open-Faced Tomato and Goat Cheese Sandwiches after I photographed this one but I held off for reasons I’ve already stated. So, I see the progress but ok.
Now that I’ve ranted about photography, let’s talk about this cake. I’m totally one of those fruit cake/pie/dessert people. Growing up, I would ask for Strawberry Shortcake for my birthday. That’s all I wanted. It’s my favorite. Can someone send me some, please?
Pineapple upside down cake comes in a close second though. But, I was eating it earlier this year and I thought: “I bet this would taste amazing with some bourbon and basil.” Guess what? I was right. It is delicious.
And, this recipe doesn’t actually burn off the alcohol from the bourbon because well, I want to get drunk on cake. Just kidding…but I did want to taste the alcohol in the dish. And, the addition of basil adds a fresh, light touch to the cake.
By the way, I totally hacked this recipe together from two amazing recipes I’ve eaten about a half dozen times and then added my own little touch and have delivered you a new summertime favorite! See the recipes here and here. Bake the cake and enjoy!
- 1/4 cup unsalted butter, melted
- 1/2 cup packed light brown sugar
- 4-6 slices of pineapple
- 1 and 2/3 cups sifted all-purpose flour
- 1/2 teaspoon baking powder
- 1/4 teaspoon baking soda
- 1/2 teaspoon salt
- 1/2 cup unsalted butter, melted
- 3/4 cup packed dark brown sugar
- 1/4 cup granulated sugar
- 1 large egg, room temperature preferred
- 1/4 cup yogurt (can sub sour cream)
- 1/2 cup whole milk
- 1/4 cup pineapple juice (reserved from the canned pineapple or use fresh)
- 1 tablespoon vanilla extract
- 1/4 stick butter, unsalted (4 Tbsp)
- 1/2 cup water
- 1/4 cup dark brown sugar
- 10 fresh basil leaves, chiffonaded
- 1/4 cup dark rum
- Preheat oven to 350°F.
- Pour in the melted butter into a 9-inch cast iron skillet. Sprinkle in the brown sugar and make sure the butter and sugar have incorporated. Add in the pineapple slices and set aside.
- Melt the butter for the cake in the microwave. In a medium mixing bowl, mix together the dry ingredients: flour, baking powder, baking soda, and salt. In the bowl of your stand mixer, mix together the brown and granulated sugar with the melted butter. Mix in the egg, yogurt (or sour cream), milk, pineapple juice, and vanilla extract until well combined. Slowly add in half of the dry ingredients until incorporated, then add in the remaining half of the dry ingredients and mix until all of the ingredients are incorporated and there are no lumps. Don’t forget to scrape the sides and mix those in.
- Pour the batter into the cast iron skillet and even out the batter. Bake for 40-48 minutes. And, loosely cover the skillet with aluminum foil at the 20-minute mark to avoid the cake browning too much.
- Melt the butter in a saucepan over medium heat. Add the dark brown sugar and water and then stir. Cook until the sugar dissolves. Then add in the basil leaves and continue cooking another 3 to 5 minutes over low heat until the mixture bubbles around the edges. Turn off the heat and carefully stir in the rum (there might be flames). Then, strain the glaze to remove the basil leaves.
- Remove the cake from the oven and pour 1/2 the glaze over the cake. Allow it to cool for 10 minutes and invert it onto a cake platter. Once the cake is inverted, pour over the remaining glaze.
- And, serve!