I didn't grow up eating Pineapple Upside-Down Cake. Like most foods that I now love, my Mom likely tried to introduce me to it back in the day. No frosting? That wasn't cake! My husband on the other hand, did grow up eating it thanks to my Grandmother-in-law. He recently started reminiscing about how delicious it is so I decided to buck up and make it. 

I dug through my cookbook shelves (so...many...books...) and pulled out Ad Hoc by Thomas Keller. While this book is his version of "down home" cooking, his recipes still have a bit of complexity to them. Not so with this cake. All ingredients you'll have on hand, no fancy techniques required.

The best part about any Pineapple Upside-Down Cake is that there are two very clear paths you can take - super easy or standard cake baking difficulty. Feel like using a boxed cake mix? No problem, make your schmear, open your can of pineapple, and away you go. Want fresh pineapple instead of canned? Mix and match to your hearts delight. In obvious Keller style, he doesn't take the easy path, but that doesn't mean it isn't right for you (or equally as delish).

The magic in this recipe is truly the schmear that you layer the pineapple on top of. The combination of butter, sugar, honey and other goodies caramelizes the pineapple during cooking and seeps down into the cake giving it extra flavor. 

For whatever reason this retro cake isn't something that you see often in restaurants or bakeries. But why not? If you make this cake for a crowd, be prepared to watch them all wax nostalgic. Enjoy!

Pineapple Upside-Down Cake 

By Thomas Keller, Ad Hoc 

(Serves 8)

Ingredients: 

Pan Schmear

• 8 tablespoons (1 stick; 4oz) unsalted butter, at room temperature

• 1 1/2 tablespoons honey

• 1/2 teaspoon dark rum

• 1 cup packed light brown sugar

• 1/4 teaspoon pure vanilla extract

Cake

• 1 1/3 cup cake flour

• 2 teaspoons baking powder

• 8 tablespoons (1 stick; 4oz) unsalted butter, at room temperature

• 1/2 cup plus 2 tablespoons granulated sugar

• 1/2 teaspoons pure vanilla extract

• 2 large eggs

• 1 tablespoon plus 1 teaspoon milk

• 1 can of sliced pineapple (Thomas calls for a fresh pineapple that you slice)

• Maraschino cherries (optional and not in the version Keller originally created)

Directions:

1. Preheat the oven to 350 degrees Fahrenheit.

2. In the bowl of a stand mixer fitted with the paddle, combine the butter, honey, rum, brown sugar, and vanilla and beat until smooth and well blended. Spread 1/2 cup of the schmear over the bottom of the 9-inch silicone cake pan. sprinkle lightly with salt. (The remaining schmear can be refrigerated for up to 2 weeks or frozen for up to 1 month; bring to room temperature before using.)

*** Note #1: I don't own a silicone cake pan. But if you do, congrats! You pass Thomas's test. My standard 9-inch pan worked out just fine, but I can imagine that it doesn't produce the perfectly smooth lines required in Keller's kitchen. Given I was using my standard cake pan, I wanted to make sure that the cake didn't stick on the bottom so I lined it with parchment paper. Not a requirement, just a safety measure for me given my tendency to leave a bit of cake in the pan.

*** Note #2: I used a bit more schmear than Thomas recommended. I'd like to say it was on purpose, but it really just was an oversight. Butter? Good. Sugar? Good. No harm done. 

3. Cut the top and bottom from the pineapple and cut away the peel. Cut the pineapple lengthwise into quarters, and cut off the core from each section. Cut each piece crosswise into 1/8-inch-thick slices. Beginning at the perimeter of the pan, make an overlapping ring of pineapple slices with the curved side facing out. Make a second ring inside the first one, overlapping the slices in the opposite direction, working toward the center of the pan. Reserve any extra pineapple for another use.

*** Note: Thomas wouldn't be thrilled, but I went ahead and used canned sliced pineapples to save myself an extra step. I'm sure using fresh pineapples makes this cake even more delicious, but this shortcut served me well. A few of my slices were a bit thick for my liking (and Thomas's) so I went ahead and carefully cut them in half. 

4. [OPTIONAL] Should you feel so inclined, dot your cake with maraschino cherries to amp up the old school factor. Thomas doesn't call for it, so feel free to skip. I used the Luxardo Maraschino cherries that are normally reserved for Manhattans in the Slattery house. So much tastier than the bright red cherries you normally find jarred.

5. Sift the flour and baking powder together; set aside. 

6. Put the butter and sugar in the bowl of a stand mixer fitted with the paddle and mix on low speed to combine, then beat on medium speed for about 3 minutes, until light and creamy, stopping to scrape down the sides as necessary. Beat in the milk. Add the flour mixture in 3 batches, beating just until combined. 

7. Pour the batter into the pan and spread over the pineapple. bake for 15 minutes. Rotate the pan for even browning and bake for another 20 to 25 minutes, until a cake tester or wooden skewer inserted into the center of the cake comes out clean. Cool the cake in the pan on a cooling rack for 20 to 30 minutes.

8. Run a knife around the edges of the cake, invert onto a serving platter, and serve warm.