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Pineapple Upside-Down Cobbler

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A pineapple cobbler served with whipped cream and luxardo cherries.
Photo by Mary Kang

While many BBQ joints offer up cobblers as a sweet reprieve from all of the smoked meats, Barbs B Q, one of our Best New Restaurants of 2024, offers up something a bit different: a unique (and irrefutably delicious) upside-down cake-cobbler hybrid. To make it, a technique not unlike that used to make a dump cake is employed: A scattering of crushed pineapple and sour cherries is strewn into a baking dish alongside melted butter, topped with a simple batter made with milk, sugar, and self-rising flour, and even more pineapple and cherries are scattered atop. A final flourish of turbinado sugar is sprinkled over top and the magic happens: The ensemble bakes into the most tender, ooey-gooey cobbler perfect for topping with whipped cream.

“Barbs’ menu is deeply rooted in traditional recipes we ate growing up reinvented with a modern twist to bring the nostalgic into the present. My mother was not a very good cook, and we hardly ever ate dessert, but when we did it was boxed pineapple upside-down cake,” says Barbs B Q investor and baker Joanne Irizarry. “For Barbs’ menu, I wanted to create a recipe that was my own version of something I ate growing up. At the other restaurant I owned, I made many different varieties of cobbler, and after some experimentation, this pineapple upside-down cobbler was born. My mother died the week I entered culinary school, and we had a very disconnected relationship at that point, so this recipe is special to me as part of the healing process. It was created in her honor.” —Jesse Szewczyk, senior test kitchen editor

Editor's Note: Canned crushed pineapple varies by brand. Some are extra juicy. Buy a few extra cans to ensure you have enough pulp after draining.

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What you’ll need

Recipe information

  • Total Time

    1 hour 30 minutes

  • Yield

    12 servings

Ingredients

¾ cup (1½ sticks) unsalted butter, melted
3⅓ cups (417 g) self-rising flour
2½ cups whole milk
1½ tsp. Diamond Crystal or 1 tsp. Morton kosher salt
2½ cups plus 2 Tbsp. (525 g) granulated sugar
36 drained sour black cherries in syrup (such as Amarena; about 1 cup), divided, plus more for serving
3 cups drained crushed pineapple, divided
½ cup (100 g) raw sugar
2 cups heavy cream
2 tsp. vanilla extract

Preparation

  1. Step 1

    Place a rack in top third of oven; preheat to 375°. Pour ¾ cup (1½ sticks) unsalted butter, melted, into a 13x9" glass or ceramic baking dish and swirl to evenly coat bottom and sides. Whisk 3⅓ cups (417 g) self-rising flour, 2½ cups whole milk, 1½ tsp. Diamond Crystal or 1 tsp. Morton kosher salt, and 2½ cups (500 g) granulated sugar in a large bowl to combine. (Batter will be loose; some lumps are okay.)

    Step 2

    Scatter 18 drained sour black cherries in syrup (about ½ cup) and 1½ cups drained crushed pineapple evenly across bottom of prepared baking dish. Gently pour batter over. Scatter remaining 18 drained sour black cherries in syrup (about ½ cup) and remaining 1½ cups drained crushed pineapple evenly over batter. Sprinkle ½ cup (100 g) raw sugar on top. Place baking dish on a rimmed baking sheet and bake, rotating halfway through, until top of cobbler is golden brown and a tester inserted into the center comes out with just a few moist crumbs attached, 65–70 minutes.

    Step 3

    Beat 2 cups heavy cream, 2 tsp. vanilla extract, and remaining 2 Tbsp. (25 g) granulated sugar in the bowl of a stand mixer fitted with the whisk attachment on medium-high speed until soft peaks form, about 2 minutes. (Or, use a hand mixer and a large bowl.)

    Step 4

    Divide warm cobbler among bowls or plates. Top each with a dollop of whipped cream and more cherries.

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