Preheat your oven to 350℉ (177℃) and line a cupcake pan with colorful liners.

In a medium bowl, mix together the semisweet chocolate chips, dark cocoa powder, and boiling water until smooth.

In a large mixing bowl, whisk together the all-purpose flour, granulated sugar, baking soda, and salt until evenly combined.

Add the cooled chocolate mixture to the dry ingredients along with the vegetable oil, large eggs, and vanilla extract. Mix until smooth.

Gently fold the wet ingredients into the dry mixture until just combined.

Scoop the batter into the prepared cupcake liners, filling each about two-thirds full.

Bake for approximately 20 minutes or until a toothpick inserted comes out clean.

Allow the cupcakes to cool in the pan for 5 minutes before transferring them to a wire rack.

In a clean bowl, beat the unsalted butter until creamy, then gradually add in the powdered sugar, vanilla extract, and heavy cream.

Fold in the Oreo cookie crumbs into the buttercream.

Heat chocolate chips and heavy cream in a small saucepan over low heat, stirring until smooth for ganache.

Pipe the buttercream onto cooled cupcakes, drizzle with ganache, and top with halved Oreos.