Preheat the oven to 350°F. Grease two 9-inch round baking pans and line the bottoms with parchment paper.

In a large bowl, combine the sugar, flour, cocoa, baking powder, baking soda, and salt.

Add the eggs, milk, oil, and vanilla extract. Mix on medium speed for 2 minutes.

Stir in the boiling water and mix until smooth.

Divide the batter evenly between the prepared pans and bake for 30 to 35 minutes, or until a toothpick inserted in the center comes out clean.

Let the cakes cool in the pans for 10 minutes, then invert them onto wire racks (to flatten domed cakes) and allow them to cool completely.

In a large mixing bowl, beat the heavy whipping cream until firm peaks form.

In another bowl, beat the cream cheese and powdered sugar until smooth.

Gently fold the whipped cream into the cream cheese mixture, then stir in the crushed Oreos.

In a saucepan over low heat, melt the chopped milk chocolate. Remove from heat and stir in the heavy cream until smooth.

Pour the ganache over the cake. (If the ganache is too runny, allow it to cool slightly until thickened but still pourable enough to drip down the sides of the cake.)

Spread the Oreo filling over the bottom layer of the cooled cake.

Carefully place the second cake layer on top.

Spoon the chocolate ganache over the top of the cake.

Garnish with chocolate chips and whipped cream, if desired.