1. Bake cake according to directions. Let cool completely. Cut into bite-size portions.
2. Mix together pudding mix and milk. Fold in half of the cool whip.
3. Layer half of the cake, half of the pudding mixture, and half of the crushed Oreos. Repeat steps.
4. Top with remaining cool whip.
5. To make the web, pour on chocolate syrup in a spiral. Starting in the middle. Draw lines with a toothpick. Add spider (for decoration).