Vincent's intensity and obsessions are what makes his character interesting. A philosopher-assassin is a fascinating juxtaposition. It is rarely done as well as it is here, but we do see it crop up from time to time. James Bond, for instance, expresses a viewpoint in Casino Royale (the book) that he lives life 90mph, right to the hilt, at all times because he knows death is around every corner. Vincent, I think, spends a lot of his time thinking about how fast life can end and he gets obsessive. Some people are like that, but Vincent realises the thin line separating life from death.
Also, although done before, the hitman-monk (hitmonk?) isn't seen often enough to feel played out. They're still rare, especially as well-written as Vincent.
Why hold out so long? His MO was to get the cabbie to drive him around, do the hits, then bump off the cabbie. It kept things simple and clean. The movie gets messy, but that's part of Vincent's philosophy: roll with it. He improvises. He keeps Max alive because he's become interested in Max and who Max is. Max fascinates Vincent. Why? Never spelled out, but he's pushing all of Vincent's buttons. He dreams big but does nothing - antithesis to Vincent's personal worldview. Maybe Vincent used to be like Max. Maybe he's afraid of being Max and that's what spurs him. Maybe he's just playing with Max like a cat.
Main gripe is talked about in the movie. "I read about this guy who gets on the MTA here, dies. ... Six hours he's riding the subway before anybody notices his corpse doing laps around L.A., people on and off sitting next to him. Nobody notices." Hiding in plain sight is a major theme here - what and who we pay attention to, big pictures, little details, etc. This kind of thing happens all the time. Okay, not gunfights and shootouts, but stuff that people miss because they just can't or won't see it.
I love this movie, and I think it's underrated.
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