Bake brownies according to package directions on the back of the box and let cool, then cut into 1" squares.
In a large mixing bowl, cream together cream cheese, cool whip, milk, oreos and vanilla for the oreo cheesecake layer. Set aside.
Layer trifle by placing half the brownies on the bottom, then half the oreo cheesecake mixture, then half the crushed oreos, then 1 cup cool whip, and then ¾ cup hot fudge sauce. Repeat layers (except for the hot fudge sauce).
To create the spider web on top, use the last ¼ cup hot fudge and draw circles around the top of the trifle, starting with a dot in the center and making your way to the outer edge.
Using a knife or a toothpick, draw out lines from the center to create a spider web look.
Refrigerate until ready to serve.
Notes
If you don’t have a trifle bowl, that’s okay, too. Try using smaller glass cups or bowls (just like this recipe does), or you can do it in a regular serving bowl if needed.