Bake the brownie layer: Prepare the boxes of brownies in a 9x13 baking dish and bake according to the package directions. Let cool completely. Cut the brownies into 1 inch cubes. You’ll have some leftover, so if you want to sneak a couple cubes while cutting, they won’t be missed.
Make the pudding layer: Prepare the chocolate pudding mix according to the package directions. Pour into a bowl and cover the pudding with plastic wrap. Be sure to place the plastic wrap right up against the pudding so it doesn’t develop a “skin” on top. Refrigerate until ready to use.
Prep the Oreos: add 10 Oreos to a food processor and pulse until it’s fine crumbs. Set aside to add to the whipped cream.
Place 15 Oreos in a bag and crush with a rolling pin or meat mallet. Leave them in larger pieces, you don’t want it too fine. Set aside for the Oreo layer.
Reserve 6-8 Oreos for the top decoration.
Add the cream cheese to a mixing bowl and whip until smooth. Add in the powdered sugar and vanilla extract and mix again. Slowly pour in the heavy whipping cream while continuing to mix until the cream is incorporated it's smooth and creamy and is soft peaks. Careful not to overmix the whipped cream. Whip just until it comes together.
Add 1 cup or so of the whipped cream to a piping bag with a large star tip to decorate the top.
Assemble: place the cubed brownies in the bottom of a trifle dish in a single layer, covering the bottom.
Spoon over half of the pudding, covering the brownies. Sprinkle half of the 15 Oreos you crushed earlier. Spread half of the whipped cream.
Repeat the layers: place more brownie cubes over the whipped cream, covering completely. You’ll probably have some brownies left over.
Add the rest of the pudding, crushed Oreos and whipped cream.
Place the whole Oreos on top (and extra crushed Oreos, if you have them) nestled in the whipped cream and pipe extra whipped cream in between the Oreos.
