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