Plus, he almost had actual sex, in 1986, ON AN AMERICAN CARTOON. And if THAT isn’t cool, I don’t know what is. And that’s not even bringing up the whole interracial thing. 
Bolt Crank, from Eat Man ‘98, is saddled with a goofy power, (he can eat anything, then re-create it out of his hand) and a goofy wardrobe (about 15 layers of green cloth, a green yarmulke, and Buddy Holly sunglasses) and he still manages to be utterly cool.
To say nothing of the goofy situations he has to endure. Anybody can be cool while turning around and slowly walking away from a giant explosion if they’re wearing a long coat that blows forward dramatically. It takes something more to be cool while cutting a truck in half with a ‘magic’ sword, that you had to cough up because it was giving you ‘indigestion,’ defending a woman who might be a prostitute, and a goofy old man giving the truck’s driver a lecture on not being evil. In the aforementioned bright green outfit.
Besides, he’s got one of those ‘honorable mercenary’ ethical codes, and a really, really deep voice that he almost never uses. Always a winning combination.
The original Bubble Gum Crisis’ Largo. Pretty much the acme of 80’s anime bad guys. I respect a man who can maintain a God complex without giggling to himself. Raw power? Check. Aside from having his asskicking super-boomer form, he was mentally linked to orbital satellite weapons letting him call down particle beams from the sky. He took on the most powerful megacorporation in the world, with no help besides an android sex toy, (somebody’s gotta drive the car) and came within about half a step of taking it over.
Proper coldblooded, manipulative attitude? “Is it dead yet? I suppose I should say, ‘Has it stopped functioning.’ It is a machine, after all. Oh, is this hurting you? Well, it’s not like you can do anything about it now.” Check.
Plus, he actually managed to kill the heroine, which is pretty impressive for any villain. (Though she was resurrected at the last minute by fan pressure. Fans ruin everything) And he ripped off the last scene from Lone Wolf and Cub. Man knows his classics. Also, he can fall straight down the side of a pyramid. Lets see Spock do that. 
Jean-Paul Rochina, from VOTOMS, was pretty cool. Not the coolest ever, but probably the coolest French guy ever. By far the coolest guy to ever be called John-Paul, anyway.
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“For the crime of injuring me, a god, I demand, as atonement, death.” How can you NOT love this guy?