When I was a kid I would rewatch things hundreds of times; My Neighbor Totoro, Star Wars, Blade Runner, West Side Story but now I don't find any use in it.
What are you getting out of There Will be Blood that has you coming back over and over again?
It's small details. Some new connection. Maybe the mood you're in changes the way you interpret a scene (or the whole movie). Maybe your personal experiences since you last watched the movie let you see it in a new (personal) light.
The same applies to books. Even more so maybe. With books you make the movie in your head, so it's more open to your interpretation, and thus changes more according to your mood etc.
I don't know about 100x, but I've reread / re-watches some movies and books to much joy.
Some things are simple enough that once or twice through and you have all that needs to be had.
Others are deep enough that you can discover and learn something new each time.
If you find the book/movie pointless the first time, no amount of reruns will change that. On the other hand, if you loved it and made you think about the issues it raised, it might be worth going through it again, but a big part of the extra deepness you find in the rerun will be placed in there by your subconscious mind.