None of them are touching Marvin Gaye. He was in a league of his own. Marvin Gaye is the coolest of the cool. The youtube video of him performing the National Anthem at the NBA final in '74 is classic Marvin Gaye.

1. I love Barack Obama. Voted for him once, will do so again. But really, he is not cool. It's nice that they found that shot of him looking like he's ready to pounce and wearing Men-in-Black sunglasses, but at the end of the day, he's actually kind of square.

2. Richard Roundtree. He was cool in Shaft, he was cool in everything else.

Of all times?
Toussaint L'Ouverture, The 2 Alexander Dumas (father and son), Le Chevalier de Saint-Georges, Marvin Gaye, Arthur Ashe, Pelé, Djimon Hounsou (pre-Lee Simmons).
Ozwald Boateng is the current coolest supreme one.

Oh….this is such a strange list….??

I guess MSIM when they say 'Brothers', then mean Afro-American. You had in your list English/Ghana-Boetang, French/Benin-Hounson….

@ Josh - I agree. Obama is not really "cool".

I have to throw in a vote for Andre 3000.

Le Chevalier de St George? A cool black man? lol!
The guy actually had a rough time being "mixed race" when he was alive.

Who is cooler than Barack? 07.07.08 : Nobody. Who can wear a PINK tie to please gays and women (?)while preserving his masculine sexiness? Nobody. Notice the position of the tie? Expressing action and energy. The glasses? This pic is a masterpiece of communication art. Gorgeous.

As much as i love Denzel and Jay (and Barack)…all of you guys know pretty well that Samuel L. Jackson is the only guy who can meet the true definition of a "cool brother" here. In terms of cool none of those gentlemen can challenge him.

Hence i mean SLJ just allowed BO to borrow his "swag" for a cool hot pic!

Sorry, RantMagazine.Boohoo, I didn't realise this was only for Americans.

The word "brother" is also used in the same sense in Canada and a few other countries.

Kwame Nkrumah for having the guts in attempting to form the United States of Africa.

msim said:Ozwald Boateng is the current coolest supreme one.

Girl if he ain't the finest man on this earth. Some men just ooze that swagger and he is one of them. I am sure my legs would turn to jelly if I ever met him in person. His wife is so lucky.

Sorry, Rachel. I must disagree.

The only thing Samuel L. Jackson epitomizes is trying-too-hard-to-be-cool. From Shaft to Frozone, he is so over the top, he takes all my energy. The Kangol, the shades, aye-yi-yi. I like my cool a bit more effortless.

Barack looks hot as hell in that pic, but he is not that cool, neither are Alexander Dumas (father or son),Le Chevalier de St George,or even Toussaint L’Ouverture (the only one who actually identified as black). Being a historical figure alone, does not make you "cool".

Samuel, Marvin, and Billy are cool.

Billy Dee Williams is the OG cool brother. Love it!

Well, lots of people in history would be thought of as 'cool' (since we can't see how corny they actually were,) but since we know all the details of these corny people's lives these days, it's hard to keep the swag now.

That said, Nat Turner was cooler. And dude on the Amistad… Cinque… was way cooler. He wasn't trrrrrrying to stay in this country. Dudes wasn't playin.

Summer : cool is more than an outfit… it's an outfit with an attitude! And SLJ has it. And as BO shows it : there is no cool without sunglasses and a bold attitude!

Billy Dee was the very symbol of coolness.

Prince was cool in Purple Rain

He was the "Denzel" of the day! The epitome of cool. He set the tone, along with Sidney Poitier for the standards of cool, and of being….a black male / man.

Any cool list that does not include Gordon Parks, Miles Davis, and Sammy Davis Jr., is not well that cool.

jay

What about Brother Malcolm X??? He is the coolest on my list. A man with no fears!

Nice. Very cool brothers. Not sure about Obama but Prince is still cool at 50