Preheat your oven to 350℉ (177℃) and prepare a cupcake pan by lining it with colorful cupcake liners.

In a large mixing bowl, combine the semisweet chocolate chips and dark cocoa powder. Pour in the boiling water, stirring gently until smooth. Allow to cool to room temperature.

In a separate bowl, whisk together the all-purpose flour, granulated sugar, baking soda, and salt.

Once your chocolate mixture has cooled, add the vegetable oil, large eggs, and vanilla extract. Beat until smooth.

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

Using a scoop, fill each cupcake liner about two-thirds full with the batter.

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

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

In a large bowl, beat the unsalted butter until creamy. Gradually add powdered sugar, heavy cream, and vanilla extract, whipping until fluffy.

Fold the Oreo cookie crumbs into your prepared buttercream until evenly distributed.

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

Once the cupcakes have cooled, pipe the Oreo buttercream onto each cupcake and drizzle with ganache. Top with a halved Oreo.

Allow the cupcakes to sit at room temperature before serving.