Wynton Marsalis exudes cool. He’s just got that presence.
I can’t stand rap but I do consider Snoop to be pretty cool. I read an interview with him in some magazine and during the entire interview he was was playing basketball on his PS2 and so was giving one word answers interspersed with the occasional expletive. When asked what were his favorite things to eat when he got the munchies he replied, “Starburst and Funyons.” I just thought that was hilarious.
He’s also surprisingly sharp. Craig Kilborn on The Late Late Show asks him really obscure stuff for 5 questions and he always “get’s it.” i’ve seen him a couple of times and clearly Craig recognizes this as well because they keep getting harder.
I think he exudes “sleaziness” more than “smoothness” personally.
I’ve only seen the trailer for Starsky and Hutch but i thought Snoop seemd pretty wooden in the bits I saw. Wooden aint cool.
See, that’s exactly it. He doesn’t care! He’s not trying to impress anybody. He’s just him.
Richard Burton.
Whoa. No offense, but I’d have a trained professional take a look at your “Poser Filter”. It might be on the fritz.
That, I’ll agree with.
I think Snoop is cool. His rapping style definitely is. He’s genuinely laid back (prolly from all the chronic). But those Nokia commercials took away from the mystique, greatly.
His acting, as another guy said, can be wooden. He doesn’t speak naturally when he acts.
I’ll second Richard Burton.
Steve McQueen.
Not the biggest guy in the world, not the most handsome. He just didn’t care what people think of him, and his on-screen charisma was a result of his true self instead of the other way around. Attitude is everything.
EZ
While taking nothing from Mr. Dogg’s coolness, I must also peep up for Dean Martin, Humphrey Bogart and Cary Grant.
Oh, and definitely Cab Calloway!
Nowhere near as cool as:
Joe Stummer
I mean, c’mon, is there even any debate about it?
For my money, Johnny Depp is currently the coolest guy in the business.
Snoop is the coolest rapper around.
Cite Just watch the interviews.
Snoop, he be kool, baby, but he be jumpin’ dat shark during dem Nokia commercials. His co-starring with Ben Stiller and Owen Whazzitsname–posers, at best–only confirms it. Once he appeared with the Hideous Dweeb from “Girls Gone Wild” fame, it was over. Case closed.
Cab Calloway is definately up there. Dean Martin and Humphrey Bogart too. I can’t comment much on Cary Grant’s coolness though. He always seemed to be the pretty boy actor to me. I’m sure I could be wrong though.
I agree, but like Keith and Iggy, He was pretty rough around the edges, As far as Cool and Smooth punk rockers go, I nominate The very dapper Dave Vanian of The Damned.
Christopher Walken. I don’t really need a punchline.
Fo’ shizzle, mah nizzle. 
Uhhh… Hello?
Cool?
Did we all forget about Shaft?
He is synonymous with cool. Around here we say, " Thats pretty Shaft."
I know I know, but it was based on a real person. Right? Right?!
Oh, yeah. And he was so very sex-ay.
More cowbell?
Actually I see him as more slick and wily. While very cool in his own way, he’s not quite smooth. Not an argument really, just my opinion.