Preheat the oven to 350°F (175°C).
Line a cupcake pan with paper liners.
In a bowl, whisk together flour, sugar, cocoa powder, baking powder, baking soda, and salt.
In a separate bowl, beat the eggs, then mix in milk, vegetable oil, and vanilla extract. Add boiling water and mix gently.
Combine wet and dry mixtures, stirring gently until just combined.
Fill cupcake liners two-thirds full with batter.
Bake for 18-20 minutes or until a toothpick comes out clean.
Cool in the pan for 5-10 minutes, then transfer to a wire rack to cool completely.
For the frosting, beat softened butter until creamy, gradually add powdered sugar, then mix in heavy cream until smooth. Fold in crushed Oreos.
Frost each cooled cupcake generously with the cookies and cream frosting.
Optional: Decorate with extra Oreo shards or crushed Oreos.