Make the Chocolate Cupcakes:
- Preheat oven to 350°F (176°C) and line a cupcake pan with cupcake liners.
- Beat butter and sugar until light in color and fluffy, about 3-4 minutes.
- Add eggs one at a time, beating just until blended.
- In a separate bowl, combine vanilla extract, water and cocoa powder. Whisk until smooth.
- Add chocolate mixture to batter and mix until combined. Scrape down the sides of the bowl as needed to make sure everything is well combined.
- In a separate bowl, whisk together flour, baking soda and salt.
- Alternate adding the flour mixture and milk to the batter. Begin by adding half of the dry mix, then mix well. Add the milk and mix well, scraping down the sides as needed. Add the remaining flour mixture and mix until smooth.
- Fill cupcake liners about 3/4 way. Bake for 15-17 minutes, or until a toothpick inserted comes out with a few crumbs.
- Allow cupcakes to cool about 2-3 minutes, then remove to a cooling rack to finish cooling.
Make the Cherry Filling:
- Combine the sugar, cornstarch and water in a medium-sized saucepan over medium heat and stir to combine. Heat until the mixture is wet and the sugar begins to melt.
- Add the cherries and stir to coat them with the sugar mixture.
- Continue to cook until the cherries start to soften and let out juices.
- Remove from heat when cherries are juicy and the juice has begun to thicken. Pour the mixture into another bowl and refrigerate until cool.
- Once cool, remove the centers from the cupcakes with a cupcake corer or knife.
- Fill the centers with the cooled cherry filling.
Make the Whipped Cream Topping:
- Add the heavy whipping cream, powdered sugar and vanilla extract to a large mixer bowl and whip on high speed until stiff peaks form.
- Pipe swirls of whipped cream on top of the cupcakes using a large round piping tip. Finish them off with some grated chocolate and a cherry. Refrigerate until ready to serve.