In a large bowl, combine vanilla pudding mix, cream cheese and milk, and mix well.
Transfer the bowl to the fridge so the pudding can thicken. Meanwhile, crush or chop Oreos into chunks. (I cut each Oreo into about 4 pieces, but you can also crush them in a large zip-top bag with a rolling pin.) Reserve any fine crumbs to sprinkle on the top of the finished pie.
Unwrap Oreo pie crust. Remove pudding from fridge and fold in Cool Whip.
Spoon half of pudding mixture into pie crust. Drizzle with strawberry syrup and sprinkle with half of Oreo chunks.
Top with remaining pudding mixture. Arrange the remaining Oreos on the top. Sprinkle with Oreo crumbs and drizzle with more strawberry syrup.