These go well with chili, as the hint of spice in the cake is mellowed nicely by the sweet bourbon glaze. These are also simple in appearance, so they are a perfect palette for decorating with piped frostings and other decorations.
For the cupcakes:
Preheat oven to 325 degrees. Line 36 muffin tins with cupcake liners and set aside.
In a medium bowl, whisk together flour, baking soda, baking powder, salt, and chili powder, and set aside.
In the bowl of an electric mixer fitted with the paddle attachment, cream together the sugar and butter until light and fluffy, about 3 minutes. Add chocolate and beat on medium speed until well combined, about 2 minutes. Add eggs, 1 at a time, mixing well after each addition. Add sour cream and vanilla and mix until well combined, about 2 minutes.
With the mixer on low speed, add the flour mixture and water in three parts, alternating between the two, and beginning and ending with the flour mixture. Beat until just combined, about 2 minutes.
Fill prepared muffin cups 3/4ths full with batter. Transfer to the oven and bake for 20 minutes, or until a toothpick inserted into the center of a cupcake comes out clean. Rotate the cupcake pans halfway through for even baking. Let cool completely before frosting.
For the glaze:
In a heavy-bottomed saucepan, over medium-low heat, combine the butter and cocoa powder and let them melt slowly, making sure not to burn the chocolate.
Whisk together the milk and vinegar and add to the butter/cocoa mix. Add the confectioners’ sugar, a little at a time, whisking as you go. Stir in the bourbon and the vanilla. Remove from the heat and allow to cool. The icing should harden a bit. When it is spreadable, ice the cupcakes.