Preheat the oven to 350 degrees Fahrenheit and line a 9X9 baking dish with parchment paper.

Mix together the brownie mix, eggs, vegetable oil and water until combined.

Pour into the prepared baking dish. Bake for 30-35 minutes until a toothpick inserted into the brownies comes out clean.

Let the brownies cool and then cut the brownies into approximately 1 inch bite size pieces.

In a small bowl, combine the chocolate pudding mix with the milk. Whisk for two minutes and refrigerate until the pudding is set.

In a large bowl, beat the cream cheese on medium speed for about 2-3 minutes or until smooth and creamy.

Reduce the speed to low and gradually add the powdered sugar. Once all of the sugar is incorporated, increase the speed to medium and beat for 1 minute, or until smooth.

Add 8 ounces of cool whip and crushed Oreos to the cream cheese mixture and gently stir until just combined.  Be careful not to over mix.

To assemble the trifle, alternate layers of brownies, the pudding mixture, Oreo cheesecake filling and chocolate syrup until you get to the top.

Top with the remaining cool whip.  Drizzle chocolate on top and sprinkle the crushed Oreos on top.

Serve immediately or cover and refrigerate until ready to serve.