I can't see Darth Vadar as being that cool. Characterization in star wars was never that deep.
I considered Chow Yun-fat for "Hard boiled" and "Crouching tiger". But he's a little petulant in the first and I find the "Wise asian martial arts master" to be a bit overplayed.
Haven't seen any of the older clint eastwood movies.
Jules's crazed ranting was fun, but he didn't deal that well under pressure and the Wolf had to come and take care of business.
I voted for
Tyler Durden (his character was written to be the definition of "cool")
Slevin Klevera (supposedly has "ataraxia", a disorder where he never worries about anything...again definition of cool)
Ferris Bueller:
[Ferris has snuck aboard a parade float]
Ferris: Ladies and gentlemen, you are such a wonderful crowd, we'd like to play a little tune for you. It's one of my personal favorites and I'd like to dedicate it to a young man who doesn't think he's seen anything good today - Cameron Frye, this one's for you."
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