Preheat the oven to 350 degrees F. Drain the cherries, reserving the cherries and syrup separately. Combine the cherry syrup, chopped chocolate, sugar, butter, and the 1/4 cup brandy in a saucepan.
Over low heat, stir until the chocolate has melted. Pour into a large mixing bowl and whisk in the egg. Sift together the flour, cocoa, and baking powder into a small bowl, then fold gently into the chocolate mixture.
Fit 12 cups of a muffin tin with paper liners and spray with non-stick oil. Pour the batter evenly into each cup. Bake for 30 minutes, or until the cupcakes are firm to the touch. Let cool for a few minutes and then transfer to a wire rack to cool completely.
Mix the remaining 1 tablespoon brandy with the remaining 1 tablespoon sugar and stir into the whipped cream. Cut a quarter-size hole into the top of each cupcake and fill with canned cherries, Frost with the whipped cream and top with shaved chocolate, and a fresh cherry.