Pineapple upside-down cake + boozy raspberry mash

Pineapple upside-down cake + boozy raspberry mash

I had plans for this week. Plans that included jumping on the popsicle bandwagon because it's popsicle week and I have a really, really delicious three-ingredient, raw fudge pop recipe that I've been meaning to share for far too long. But then I posted a photo of pineapple upside-down cake and some of you lost your shit. Like, (one of you in particular) emailed me three times over the course of 24 hours-lost your shit. And then proceeded to tell me that if I didn't post the recipe by the end of the week, OLC was going to be removed from your reader. THE HORROR. Although my typical (pre-wedding) response would have been this (what a bitchy feisty, little thing, I used to be), I crafted an email (accompanied by this GIF, instead) and explained that things have to be tested and photos have to be taken and then edited, and how all of that takes time that I currently do not have because I just got back from my wedding and am neck-deep in two too many ambitious projects that no one should try to tackle simultaneously. There was a day of no emails followed by an apology. And a half-joking, "Ok, I guess I'll give you until next week."

I laughed - so hard that I cried - because I realized that people can be so damn kooky (read: batshit crazy) when it comes to food. And I am no exception. I mean, I was so impatient at dinner the other night that I couldn't wait for Thom to finish carefully spooning salsa over his tacos before barking SWEET BABY JESUS I AM EATING WITHOUT YOU! And then I devoured an entire taco before he took his first bite.

(They have a word for that sort of unsavory behavior. And it's called being hangry.)

So here I am at 9PM on a Tuesday, eating dark chocolate nonpareils in bed and getting ready to binge watch start season three of OITNB (by the way, my friend wrote a brilliant piece on the show) (which I don't recommend reading unless you've started season three or thoroughly enjoy spoilers, like me). But before I reacquaint myself with the fine ladies of Litchfield Penitentiary: Here ya go, Samantha. Here's your pineapple upside-down cake that I spent all of Sunday morning photographing, for you. Then all of Monday evening - ignoring my husband (!) - so that I could edit the photos and compile them into this post, for you. And if you don't make this cake and email me a photo of it (preferably while you're shoveling it into your face) by tomorrow at midnight, I'm registering you for every Cute Kid Contest I can find on the internet.

I'm kidding. I'll give you until 10AM, Thursday morning.

Pineapple juice
Into the bowl
Brown suga
Boozy raspberry mash
Pineapple upside-down cake + boozy raspberry mash
Pineapple upside-down cake + boozy raspberry mash
Pineapple upside-down cake + boozy raspberry mash
Pineapple upside-down cake + boozy raspberry mash

Notes: I've made this cake with fresh raspberries and blackberries (the color from them doesn't bleed the way the mash does), but prefer the texture and look of berries have been smashed with a bit of booze. I've also made this cake with both fresh and canned pineapple, and have to say I prefer pineapple that hasn't been sitting on a grocery store shelf for six months. If you don't want the topping to be too sweet, you can omit the coconut oil and reduce the brown sugar to one tablespoon, and simply sprinkle it over a lightly greased pan. And if you want your cake to be aesthetically pleasing (pineapple upside-down cakes are inherently ugly, you know), omit the oil + sugar topping and just lightly grease your baking pan and sprinkle with 2-3 teaspoons of brown sugar, instead.

And because this recipe wouldn't have been possible without him: big thanks to Todd, the kind employee at my neighborhood Whole Paycheck Foods (SUP CAP HILL!) who dropped some serious pineapple knowledge on my ass while I was shopping for the perfect pineapple for this cake. And when the store didn't have any Todd thought were suitable for baking (I took an unripened one home, anyway), he sent me on my way with one of their peeled + cored varieties, and is basically the only reason you're looking at this recipe today (instead of two weeks from now).


15-20 fresh raspberries
1 tablespoon golden (or spiced) rum

2-4 tablespoons brown sugar
2 teaspoons refined coconut oil
5 fresh pineapple rings, about 1/2" thick

1 3/4 cups (225g) all purpose unbleached flour
1/4 teaspoon baking soda
1/2 teaspoon baking powder
1/2 teaspoon fine sea salt
2/3 cup (148g) cane sugar
1 tablespoon (11g) potato starch

1/3 cup (68g) refined coconut oil, melted (but not hot)
1 1/2 teaspoons pure vanilla extract
1 tablespoon (14g) golden (or spiced) rum
1/2 cup (110g) soft silken tofu puree
1/2 cup (120g) pineapple juice

Preheat oven to 350˚F. In a small bowl, smash the raspberries with a fork and mix with rum; let sit for five minutes. Line an 8" square baking pan with parchment paper. Lightly grease with oil then sprinkle with brown sugar and line with pineapple slices. Remove raspberries using a fork, making sure to shake off the excess liquid, then stuff into pineapple openings; set pan aside.

In a medium sized mixing bowl, sift together the flour, baking powder, baking soda, and salt; set aside. In a large mixing bowl, stir together the cane sugar and potato starch, then whisk in the coconut oil. Whisk for 30-45 seconds, just until the starch starts to act as a binder. Add the vanilla extract, rum, and tofu, and mix until combined. Stir in the pineapple juice and 2/3 of the flour mixture, and whisk until the clumps disappear. Using a spatula or wooden spoon, stir in the remaining flour. Pour batter over the pineapple slices and spread with the back of a spoon. Tap on counter to ensure the batter squeezes between the pineapple slices. Bake at 350˚F for 36-40 minutes, or until a toothpick comes out clean. Remove from oven and cover with a towel for at least 20 minutes, which will trap steam and ensure tenderness. Invert onto a wire rack and cool for at least an hour. Cake will keep for up to two days, but is best on the first day.

Yield: 10 slices