Preheat the oven to 350°F (180°C) and line 2 cookie sheets with parchment paper. Set aside.

In the bowl of a stand mixer fitted with a paddle attachment (or with a large bowl and a handheld electric mixer), cream the butter, brown sugar, and granulated sugar together on High until pale and fluffy, about 3 minutes.

Add the eggs, one at a time, followed by the vanilla extract. Scrape down the sides of the bowl once or twice to ensure even mixing.

In a medium bowl, whisk together the flour, cocoa powder, baking soda, baking powder, and salt, then turn the mixer to low and gradually mix into the butter mixture. Finally, fold in 30 crushed Oreos until just combined.

With a ½ cup (4 oz/115 g) measuring cup, measure about 2 scoops of dough and form into a ball.

Place the ball of dough on a prepared baking sheet and use the back of the measuring cup to press down into the center of the dough to create a large indent (this will ensure proper spreading and even baking). Repeat with the remaining cookie dough, placing the balls of dough about 2 inches (5 cm) apart.

Bake the cookies, one sheet at a time, for 10-12 minutes, just until the surface starts to look dull.

Let cool on the pan for 10 minutes before transferring to a wire cooling rack to cool completely.

In the bowl of a stand mixer fitted with a paddle attachment (or with a large bowl and a handheld electric mixer), beat the cream cheese on medium-high until smooth, then add the butter and vanilla extract and continue beating until well blended.

Lower the speed to low and gradually add the powdered sugar until combined.

Fill a piping bag fitted with a medium round tip with the frosting and, starting at the center of a cookie, pipe a swirl of frosting almost all the way to the edge of the cookie. Top with some of the remaining 10 crushed Oreos.

Serve immediately or store in a single layer in an airtight container for up to 3 days.