From Life, Love and Sugar, edited for ease and clarity
1 box brownie mix (I used Ghirardelli)
Oreo Cheesecake Layer
2 8-ounce packages cream cheese, room temperature
3/4 cup granulated sugar
3 tablespoons milk
2 teaspoons vanilla extract
1 1/4 cups heavy whipping cream, cold
1/2 cup powdered sugar
1 1/2 cups Oreo crumbs (about 16 Oreo cookies)
Whipped Cream Layer
1 1/4 cups heavy whipping cream, cold
1/2 cup powdered sugar
1 teaspoon vanilla extract
Extras
1/2 cup Hershey‘s special dark chocolate syrup
10 Oreo cookies, rough chopped (you should have 5 to 6 left in the package, use those as a garnish on top)
Prepare brownies according to package directions. Set aside to cool, and then cut into small squares.
Place cream cheese and sugar into the work bowl of a stand mixer. Beat on high speed until smooth and creamy. Beat in milk and vanilla extract until well combined. Set aside. In another bowl beat the heavy whipping cream with the powdered sugar to stiff peaks. Slowly fold whipped cream mixture into cream cheese mixture until combined. Fold in Oreo cookie crumbs.
Beat remaining heavy whipping cream with powdered sugar and vanilla extract until stiff peaks form; set aside.
To assemble trifle, divide brownies in half. Crumble half of them on the bottom of the trifle dish. Top these with half of the cheesecake filling, smoothing it to cover with a spatula. Sprinkle 3/4 of the chopped Oreos on top of the cheesecake filling. Drizzle chocolate sauce overall. Layer 2/3 of the whipped cream on top of the crumbled Oreos spreading to even out. Add another layer of brownies, then remaining cheesecake filling. Top trifle with remaining whipped cream, either swirling or piping it on top in a decorative fashion. Continue decorating top with remaining chopped Oreos and chocolate syrup. Place whole Oreos upright on top in little mounds of whipped cream. Refrigerate until ready to serve. This keeps in the refrigerator up to three days.