Prep the pan: Line a 9x13-inch pan with parchment, leaving an overhang to lift the dessert later.
Lightly grease the sides to prevent sticking.
Make the Oreo base: Crush about 28–30 Oreos into fine crumbs using a food processor or a zip-top bag and rolling pin. Stir in the melted butter until the crumbs look like wet sand.
Press the crust: Pour the crumb mixture into the pan. Press firmly into an even layer with the bottom of a measuring cup.
Freeze for 10–15 minutes to set.
Beat the cream (no overmixing!): In a chilled bowl, whip the heavy cream to stiff peaks. Set aside.
Make the creamy base: In a separate bowl, beat the softened cream cheese until smooth (about 1 minute). Add the sweetened condensed milk, vanilla, and a pinch of salt.
Mix until silky and lump-free.
Fold in the whipped cream: Gently fold the whipped cream into the condensed milk mixture in two additions. Keep it light and airy.
Add the cookies: Roughly chop or crush 10–12 Oreos into bite-size pieces. Fold them into the filling.
If using mini chocolate chips, fold those in too.
Assemble the first layer: Spread half the creamy filling over the chilled crust. Smooth the top with an offset spatula.
Middle “sandwich” layer: Arrange a snug layer of whole Oreos (about 16–18) on top of the filling. Don’t worry if there are small gaps.
Top layer: Spread the remaining filling over the cookies.
Smooth the surface. Crumble 4–6 Oreos over the top for a crunchy finish.
Freeze: Cover the pan tightly with foil or plastic wrap. Freeze for at least 6 hours, preferably overnight, until firm enough to slice.
Slice and serve: Lift the dessert out using the parchment.
Let it sit at room temperature for 8–10 minutes to soften slightly. Use a warm, sharp knife to cut into bars or squares, wiping the blade between cuts.