Preheat oven to 350 degrees. Combine chopped chocolate and cocoa in a bowl, pour hot water, and whisk until smooth. Chill in the fridge for 20 minutes (or 10 in the freezer), stirring halfway.
Simultaneously, in one bowl, blend flour, granulated sugar, salt, and baking soda. In a separate bowl, combine canola oil, eggs, vinegar, and vanilla. Next, pour the chocolate mixture into the oil mix and stir until thoroughly combined. Finally, add the flour mixture and whisk until a smooth consistency is achieved.
Divide the batter evenly into 12 paper-lined muffin cups, filling each with about 1/4 cup. Bake in the preheated oven until a toothpick inserted into the center comes out clean, which should take around 17 to 19 minutes. Afterward, allow the cupcakes to cool in the baking tin for a few minutes before transferring them to a wire rack for complete cooling.
Portion batter evenly into 12 lined muffin cups, each receiving about 1/4 cup. Bake until a toothpick comes out clean from the center, which typically takes 17 to 19 minutes. After a brief cooling period in the baking tin, transfer the cupcakes to a wire rack to cool completely.
Start by piping whipped cream onto the cupcakes, then top each one with a cherry and garnish with finely chopped chocolate or sprinkles. Afterward, store them in an airtight container in the refrigerator. Prior to serving, allow them to rest at room temperature for approximately 20 minutes.