Preheat the oven to 350°F. Line a 9 x 13-inch metal baking pan with parchment paper, leaving an overhang on the sides.
Beat the softened butter, granulated sugar, and brown sugar until creamy.
Add the egg and vanilla and mix until combined.
Add the flour, baking soda, and salt. Mix just until no dry flour remains, then fold in the chocolate chips.
Press the cookie dough evenly into the prepared pan.
Arrange exactly 24 whole Oreos in a single layer over the cookie dough.
Whisk the melted butter and granulated sugar together for the brownie layer.
Add the eggs and vanilla and whisk until smooth.
Whisk in the flour, cocoa powder, and salt just until combined.
Fold in the semi-sweet chocolate chips.
Pour the brownie batter over the Oreo layer and spread it gently with a rubber spatula.
Bake at 350°F for 40–45 minutes, until the edges are set and the center is slightly soft.
Cool completely in the pan on a wire rack for at least 1 hour.
Lift the brownies out using the parchment overhang. Chill for 30 minutes if desired for cleaner cuts, then slice into 15 bars.