Re: Coolest character in film?
I agree with the already mentioned Shaft, Jules Winfield, and Doc Holliday.
And while he wasn't cool for the duration of the entire film, Adam Sandler's character in Punch Drunk Love may have been the coolest SOB alive (well, he's a fictional character, so he's not really "alive") for those few moments when he beat the [censored] out of the phone sex scammers. That was truly bad-ass.
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