This was the only film on the list that I had never come across before. Not only had I heard nothing about it, I didn't even know it existed. Parts of me kind of wish I could go back to that state...
I like subtlety in film, I like ingenuity and I like a film to be believable in its logic (not necessarily that the storyline must be plausible just logically possible!). Oldboy is certainly different and interesting, but on the other two it very much falls down.
The premise of the movie is very clever, someone gets imprisoned as an act of revenge which in turn leads to the released prisoner seeking revenge on his jailer. Which sounds fairly straight-forward an idea that I couldn't possibly see as ingenious in any way shape or form. But it is the twists and turns on that story that make it so clever.
The prisoner is held captive for no reason, then released without any explanation. As the story unfolds the prisoner has to figure out who the mysterious man is and what he has done to deserve this revenge. Still fairly straightforward until we hit the big twist at the end, which personally is up there with the Usual Suspects and Seven as quite unexpected.
What doesn't really make sense to me though is the initial act that caused the imprisonment. I just don't buy the idea that someone would go to such lengths to seek revenge for such a minor indiscretion. A throwaway line to a friend about something you saw leads to you being imprisoned and your family killed?! It just doesn't make sense!
In terms of subtlety, I am not the most squeamish person in the world but there are parts of this movie that had me peaking at the screen through my hands. In Kill Bill the outlandish nature of the fighting was pretty damn funny, in Oldboy it just comes across as a bit over the top, without reaching the comic book level. Was it really necessary for the Director to show us that many teeth being pulled out of people's mouths?!!?
Overall, clever idea but I think I would liked to have seen it done slightly differently. Not sure it deserves its place in the Top100 but some quite clever parts just about redeems the movie.