If you can judge a man by his friends then no one could be cooler than Screamin Jay Hawkins: Jim Jarmusch, The Clash, Nick Cave, Serge Gainsbourg and Tom Waits are all buddies and collaborators with this flamboyant, majestic entertainer.
If you're more superficial and believe a man can be judged by the way he looks, he still has everyone beat with his Dracula capes, brocade suits, smoking skull canes, and coffins. He also has tons albums to recommend him as a significant contributor to the world of blues and entertainment (including one hilariously titled Black Music for White People).
But what do you think?