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TO MAKE THE CUPCAKES: Preheat the oven to 350F.
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Grease standard-size (3-inch-diameter) muffin cups with butter or cooking spray, sprinkle with flour, and knock out the excess.
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In a large bowl, stir together the flour, granulated sugar, brown sugar, cocoa, baking powder, baking soda, and 1/2 teaspoon salt.
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In a bowl, whisk together the buttermilk, melted butter, eggs, and 2 teaspoons vanilla.
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Pour the egg mixture into the flour mixture and whisk until combined.
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Add the boiling water and whisk until the batter is smooth.
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Evenly spoon about 1/4 cup of batter into each of the prepared muffin cups, filling about 3/4 full.
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Bake until a toothpick inserted into the middle of a cupcake comes out clean, about 15 minutes.
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Remove the cupcakes from the pan and cool on wire racks about 20 minutes before filling and icing.
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TO MAKE THE CREAM FILLING: Using an electric mixer fitted with the paddle attachment, beat the 1 cup butter and powdered sugar on medium-high speed until the mixture is light and fluffy, about 5 minutes.
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Add the 1/4 cup whipping cream and beat for 1 minute more.
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Set aside.
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TO MAKE THE ICING: Set the chocolate in a bowl.
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In a saucepan set over medium heat, bring the 1/2 cup whipping cream to a gentle boil.
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Pour the hot cream over the chocolate, stirring constantly until it melts completely.
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Stir in the syrup, 1 teaspoon vanilla, and pinch of salt.
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Let the icing cool for about 20 minutes before spreading over the cupcakes.
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TO ASSEMBLE THE CUPCAKES: Using a spoon, fill a pastry bag fitted with a round number 10 tip three-quarters full with the cream filling.
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Set the cupcakes upside down on a work surface.
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For each cupcake, push the metal pastry tip into the center of the bottom of the cupcake three-quarters of the way in, squeezing filling out as you go.
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Refill the pastry bag as needed and repeat with each cupcake.
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(There will be extra filling; youll use it to decorate the tops of the cupcakes.)
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Turn the cupcakes right side up and use a spatula to ice their tops.
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Let the icing harden for about 15 minutes.
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TO FINISH: Embellish the top with curlicues of the leftover filling piped with the same number 10 tip; 2 or 3 plumpish curls will fit on top of each cake.
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For a more authentic look, spoon the leftover filling into a plastic sandwich bag, snip off a tiny corner, and squeeze out the filling to make 5 or 6 thin curls on each cupcake.
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The cupcakes can be made, filled, and stored on a tray or platter and covered in plastic wrap up to 1 day in advance without refrigeration.
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Covered and refrigerated, theyll keep 2 days.
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Ice before serving.
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No buttermilk?
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Heres a substitute: put 1 tablespoon lemon juice or distilled white vinegar in a liquid measuring cup.
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Add enough milk to measure 1 cup and stir.
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Let the mixture sit for about 15 minutes; stir again.
