Heat oven to 350°F. Prepare two muffin pans with cupcake liners.
In a large mixing bowl, whisk together the sugar, flour, cocoa, baking powder, baking soda and salt in large bowl.
In a second mixing bowl, whisk together eggs, milk, oil, vanilla extract until evenly mixed.
Add the egg mixture to the flour mixture and stir together until just combined. Do not overmix. Stir in the boiling water. Batter will be thin.
Fill each cupcake well about 3/4 cup full of batter. Bake for 22-25 minutes or until wooden pick inserted in center comes out clean, rotating pans halfway through baking. Remove cupcakes from pans and allow to cool on a wire rack. Cool completely. Repeat with the additional cupcake batter (about 6 additional cupcakes)
For the frosting (note this is a triple batch, I always make 3 batches to frost all these cupcakes. If you like high swirls like I do then you will want to make a triple batch as well - but you can cut down the amount if you want) combine the butter and powdered sugar and mix on low, then increase the speed for 2-3 minutes until light and fluffy. Add in your vanilla extract, peppermint extract, and heavy cream. Beat on medium-high for 8 minutes.
With a pastry bag and tip attached, pipe the frosting on each cupcake. Decorate with a cookie. I also crushed up a few cookies and decorated with the cookie crumbs. Store at room temperature for up to 2 days. Refrigerate for up to 3 days, just bring back to room temperature before serving.