Let's talk Coolest Film Characters Ever...with a caveat
The caveat is they must be at least 20 years old. Why 20 years? I don't know, I'm just thinking of cool characters that have stood the test of time, instead of "The Joker", "Iron Man" etc. If you must choose more recent characters, so be it, but I'm going for classic film characters.
Here is my starting list off the top of my head, feel free to add your own:
Cool Hand Luke - Obviously, since were on the Cool Hand Luke board. "Sometimes nothin' is a pretty Cool Hand." He is really cool, and I love how the other guys (especially George Kennedy) go from wanting to pummel him to wanting to be him.
Blondie (The Good The Bad and the Ugly) - I think Eli Wallach owns this movie, but Eastwood is really cool.
Harry Lime (The Third Man) - The way he makes his entrance and the cuckoo clock speech etc. make you understand why everyone likes him, despite his shady behavior. He's cool!
Quint (Jaws) - I just always thought he was cool, the bandana, the boat, the verbal abusing of Brody and the verbal sparring with Hooper...even when he gets eaten he's cool :-)
Chuck Tatum (Ace in the Hole) - A lesser known character, but I think Kirk Douglas is great in this movie. Kind of a sleazy guy, but cool, especially at the beginning when he's trying to get a job at the town paper. Check out the Memorable Quotes http://www.imdb.com/title/tt0043338/quotes or the first 5 minutes of the movie http://www.youtube.com/watch?v=ZSB54h-rvfU and see what you think. You can't go wrong with Billy Wilder...
...which leads me to Walter Neff (Double Indemnity) - Fred MacMurray (yes, Fred MacMurray) is really cool in this classic noir. "Good-bye baby."
JJ Sefton (Stalag 17) - Hmmm another Billy Wilder movie. William Holden is really cool as the guy who they think is a rat cause of all the perks he's got.
I'm sure there's much more, but that's what comes to mind off the top of my head. And as for recent characters, I really like the villian in Oldboy. A messed up twisted guy, but always cool, even in a floppy hat :-)