To prepare the strawberries, hull and halve or slice them (halve smaller berries, thinly slice large berries). Transfer about 1/4 of the berries to a large bowl and mash with a fork. Add the remaining berries and 1/2 cup of sugar and toss to combine. Cover with plastic wrap and let stand for 30 minutes.
To make the shortcakes, butter a cast iron skillet or 9x13-inch baking pan (or coat with cooking spray).
In a large bowl, whisk together the flour, 1/3 cup sugar, baking powder, and salt. Add the butter and use a pastry cutter or two knives to work the butter into the flour until the butter is pea-size and coated with flour.
In a small bowl, whisk together the 3/4 cup cream, egg, and vanilla. Fold the cream mixture into the flour mixture using a rubber spatula. When the mixture is crumbly, use your hands to form a loose dough. If the mixture is too dry to come together, add 1 tablespoon cold cream or ice water.
Transfer the dough to a lightly floured surface, or pastry cloth, or between two pieces of parchment paper and roll into a 10x13-inch rectangle (this doesn’t have to be exact). Fold the dough in half lengthwise, then fold in half crosswise. Roll gently until the top is smooth and the dough is 1-inch high.
Dip a 2 3/4-inch to 3-inch biscuit cutter into flour and cut out 6 to 7 biscuits, re-rolling the scraps as needed. If needed, hand-shape the last shortcake.
Transfer the shortcakes to the prepared pan (fit them snuggly; they will help each other rise) and refrigerate or freeze for 20 minutes. NOTE: If you’re using a cast iron pan, transfer the shortcakes to a plate to refrigerate or freeze. Transfer them to the pan just before baking.
Preheat the oven to 425 degrees.
Brush each shortcake with a little heavy cream and sprinkle with sugar.
Bake for 18 to 22 minutes, until the tops of the shortcakes are browned, and the edges are golden brown. If you’re unsure if they’re finished cooking in the middle, lift the top of one shortcake and peek in the middle. If the center is still gooey, keep cooking. If the tops are getting too browned, loosely cover with foil. Cool for 5 to 10 minutes before removing the shortcakes from the pan.
Meanwhile, to make the whipped cream, in the bowl of a mixer fitted with the whisk attachment, beat together the 2 cups of cream, powdered sugar, and vanilla. Beat on high speed until soft peaks form, about 2 to 3 minutes, depending on your mixer. Refrigerate your whipped cream until ready to use.
To assemble the shortcakes, split the biscuits in half crosswise. Top the bottom half with strawberries and whipped cream. Top with the second half of the shortcake, whipped cream, and strawberries. Serve immediately.